We talked about this in the episode :

"And if you don't define that enough, you just keep changing your rules. Goalposts keep moving. You have to define your enough and then do not change the goalpost."

Before you can chase any fire number, you need to know your enough.

The minimum viable amount that keeps you safe if everything stopped tomorrow. Not luxury. Not your aspirational lifestyle. Just stable.

That number starts with your fixed costs.

Rent. Utilities. Groceries. Transport. Obligations that don't stop regardless of your income.

Separate those from your variable costs, the things that flex when life changes. Your fixed costs are your floor, and your floor is where your real fire number begins.

From there, the math is straightforward.

Multiply your annual survival spend by 25. That is your minimum fire number, based on the 4% withdrawal rule. If your survival spend is $60,000 a year, your number is $1.5 million. That is survival fire.

If you want your current lifestyle with a bit more flex, double your survival spend to $120,000. Multiply by 25. You are looking at $3 million. That is base fire.

If you want full margin, five trips a year, kids' college, genuine comfort, your spend sits around $150,000. Multiply by 30. Your number is $4.5 million. That is comfortable fire.

Your fire number is not one number. It is a range. And it starts far lower than the headlines suggest.

Income layering and diversification makes every number in that range more achievable. A portfolio of income sources like Dividends, rental income, consulting, digital products. If other income covers part of your monthly spend, you withdraw less from your portfolio. Compound interest keeps working. The math becomes far more forgiving than most fire conversations admit.

We ended the episode with one question that I think lands everything.

Your assignment: Calculate three numbers. Your survivor fire. Your base fire. Your comfortable fire. Then ask yourself which one gives you peace. Not prestige. Peace. That is your real enough. Write it down.

FIRE doesn't have one definition. For some it's options. For some it's agency. For me it's peace. My money compounding quietly while I live my life. Whatever your word is, find it.

You might be interested in listening to these pods

• Should you invest or pay off your debt

• What FIRE means

• From Credit card debt to FREEDOM

Two Paths to FIRE is hosted by Olamide Amosu. New episodes weekly.

I used to think acquisitions were only for PE firms. Big corporations. Institutional money. That was the frame the only way to own multiple businesses was to have millions in backing and a team of lawyers.

Then I took a class on Entrepreneurship Through Acquisition (ETA) during my MBA and everything shifted.

I learned that not all founders want to sell to private equity. Many prefer selling to people like me, people who’ll actually carry what they built instead of dismantling it for parts. Business school taught me what to look for: profitability, tenure, revenue, retention. It taught me about self-funded acquisitions where you own outright. Search funds too. It all felt approachable.

Except it didn’t. Not really.

What business school never showed me was how small you could actually start. Four figures. Not millions. The framing was all institutional structures. No breakdown of digital acquisitions as their own category. No actual path from learning to buying.

Then I met Natia Kurdadze. Natia is an experienced IP Strategist & Serial Entrepreneur.

How She Got Into Acquisitions

I wanted to understand what drew her to this specific path.

Olamide: Walk me through how you got into business acquisitions. What was the first deal actually like?

Natia: I’ve always been obsessed with building digital businesses. I realized that buying something with existing customers, revenue, and proven demand is often less risky than starting from zero.

I didn’t start in business, I started in intellectual property. That taught me what makes a business valuable and, just as importantly, what makes one fragile.

Olamide: So your first deal, and how did it change your tragetory?

Natia: - My first opportunities were small digital businesses, apps, and SaaS products.

I fell in love with ideas and started looking at businesses like assets. Everything became numbers, systems, customer retention, and growth opportunities.

Today I look at acquisitions as another growth channel. Sometimes the best startup isn’t the one you build. It’s the one that’s already working but has an exhausted founder.

How Natia Actually Finds Deals

I wanted to understand where the real opportunities were hiding. Most people think you find deals on marketplaces. Natia’s answer surprised me.

Olamide: You mentioned sourcing from platforms, but also direct outreach. How much of your deal flow actually comes from unlisted deals versus the listed marketplaces?

Natia: I don’t rely on one marketplace. I source through platforms like Acquire.com, Flippa, TrustMRR, private founder communities, X, LinkedIn, Indie Hackers, Reddit, and increasingly through direct outbound.

The biggest edge isn’t finding listings.

It’s finding businesses before they become listings.

Olamide: So where are you actually finding these founders?

Natia: I buy from are developers who I have worked with in my IP role, and some acquired through my growth network. Once you start buying, more developers start reaching out and sharing opportunities with you.

Olamide: How do you actually approach a founder who isn’t advertising? Doesn’t that feel cold or pushy?

Natia: Most founders don’t wake up thinking, “I’m selling today.” But many are burned out, changing careers, or simply stuck. Those conversations create the best deals.

When I evaluate opportunities, I ask a few simple questions: Is revenue consistent? Is growth organic or entirely paid? Is customer acquisition repeatable? Is the codebase maintainable? Is there founder dependency? Could I improve this business within 90 days?

Most listings fail those tests.

The Due Diligence That Actually Matters

I realized most people skip this part, which is exactly why they overpay or buy broken businesses.

Olamide: When you’re evaluating a deal, what documents or access do you actually need to see? And how do you verify the numbers are real?

Natia: I never rely solely on screenshots. I request: Stripe, LS, Creem or Paddle Screen recording during the meeting. Analytics access, Google Search Console, Customer retention, Churn, Traffic sources, Financial statements, Infrastructure costs.

Olamide: What specifically are you looking for in those recordings? Like, what would make you walk away from a deal?

Natia: Revenue is only one part of the story. I also care about operational complexity. A business making $8,000 MRR with two support emails per day is often more valuable than one making $20,000 MRR that’s completely dependent on the founder.

Olamide: So when you’re calculating what to pay for a business, how do multiples actually work?

Natia: As for multiples, it depends on growth, margins, churn, and risk.

I’m less focused on buying cheaply than buying businesses where I already know exactly how I’ll create additional value.

But here’s what matters: I’m not just buying cheaply. I’m buying businesses where I already know how I’ll add value. If I see SEO opportunity, or a pricing increase that’ll work, or a feature gap customers have mentioned, that’s worth paying a higher multiple for, because I know exactly how I’ll improve it.

The Real Entry Cost (Spoiler: It’s Smaller Than You Think)

Olamide: This is what surprises people most. Everyone assumes you need serious capital. What’s the real entry cost to get started?

Natia: The biggest misconception is that acquisitions require millions. They don’t. Many digital businesses sell for the price of a used car. You can start with four figures, or even less if you’re partnering with someone, using seller financing, or structuring creative deals. The bigger investment is learning how to evaluate businesses. Knowledge compounds much faster than capital.

Olamide: so like $2k, $5k, $10k? What’s a realistic first acquisition look like?

Natia: You need to learn the metrics first. A seller’s aspiration price is typically around a 3.5x to 4.5x ARR multiple. Your target ZOPA (Zone of Possible Agreement) should be closer to a 2.5x to 3x ARR multiple, depending on the business’s quality, growth, and risk profile.

For someone starting with limited capital:

First, learn the metrics. Second, study dozens of listings without buying anything. Third, talk to founders. Fourth, understand SaaS metrics, cash flow, retention, and acquisition channels. Then save enough capital for a small acquisition, or structure a creative deal through seller financing or partnerships. Don’t rush. The best investors say no far more often than they say yes.

The 30-60-90 Day System

Olamide: Once you close a deal, what’s your actual plan? What do you do in those first weeks?

Natia: The first mistake new buyers make is changing everything immediately. I do the opposite.

First 10 days: I observe. I document systems. I understand customers. I fix obvious leaks.

Days 10–30: I automate operations. Improve onboarding. Increase retention. Improve pricing if appropriate. Clean up analytics.

Days 30–60: Now we focus on growth. SEO. Content. Partnerships. Distribution. New acquisition channels. AI automation. New features.

The goal isn’t explosive growth. It’s building a stronger, more valuable business that becomes increasingly independent of me.

Olamide: How much do the numbers typically move in 90 days?

Natia: It depends on what’s broken. If it’s a pricing problem, or If it’s marketing, if you optimize SEO.

Building a Portfolio

Olamide: You mentioned a $10K MRR target. Is that coming from multiple acquisitions, or are you also building products? What does your actual income breakdown look like?

Natia: I build products. I invest. I create content. I advise founders. Some assets I’ll hold for long-term cash flow. Others I’ll improve and eventually sell. The objective isn’t flipping businesses. It’s building multiple independent income streams that don’t rely on one client, one employer, or one platform.

Olamide: Love to hear about the 100 Apps Challenge. What’s that actually about?

Natia: The goal isn’t simply building one hundred apps. It’s creating a diversified portfolio of digital assets, learning faster through repetition, and identifying breakout winners. Some apps will remain long-term cash-flow assets. Others may eventually be acquired. The portfolio itself becomes increasingly valuable over time.

Olamide: How many have you sold so far as a part of the challenge?

Natia: 6

When & How to Sell (or Hold)

Olamide: You mentioned sometimes you flip businesses, sometimes you hold them. How do you decide? And when you do sell, what’s the actual process?

Natia: I don’t buy businesses planning to sell immediately. I improve them until the next opportunity cost becomes larger than continuing to operate them.

The exit process itself is fairly straightforward:

• Organize clean financials

• Document SOPs

• Reduce founder dependency

• Prepare metrics

• Find strategic buyers

• Negotiate terms

The easier a business is to operate, the higher the multiple buyers are willing to pay.

Olamide: Walk me through the actual math. If I’m selling a business, what multiples should I expect?

Natia: It depends on growth, margins, churn, and risk. For example, if a business is generating $500 MRR ($6k ARR annually), you could sell it for approximately 12 × $500 × 3.5 = $21,000. (Revenue matters the most)

But that’s assuming a 3.5x multiple. Other variables might be at play.

What Year One Actually Looks Like

Everyone asks about returns. But first-year expectations are usually wrong.

Olamide: Let’s be real about this. Someone hears “digital business acquisition” and thinks they’ll make $50k profit in their first year. What should they actually expect?

Natia: The range is huge depending on the deal. Most people expect life-changing income after one acquisition. Reality is slower. Year one is about learning. You’ll probably spend more time sourcing than buying. You’ll reject dozens of deals. You’ll make mistakes. If you stay disciplined, your first acquisition becomes a foundation, not a finish line.

Olamide: What are the mistakes that trip people up in year one?

Natia: The biggest mistakes are: skipping due diligence, overpaying, chasing hype, ignoring customer retention, trying to change everything immediately.

What Financial Freedom Actually Looks Like

Olamide: When you say financial freedom, what does that actually mean to you? Is it a number, or is it something else?

Natia: Financial freedom isn’t owning a Lamborghini. It’s owning your calendar and location. It’s waking up because you want to, not because you have to. It’s having systems that generate income while you focus on creating, learning, and spending time with people you care about. For me, that’s the real goal. Money is simply the tool that buys freedom.

WHY THIS MATTERS

Most people assume acquisitions need institutional backing. Massive capital. Business school made it sound doable but still out of reach. Natia made it real.

There are thousands of digital businesses right now: generating revenue, running smoothly, owned by people who are done. These aren’t failures. They’re working assets. Someone just needs to know how to improve them. And you don’t need investors or search funds to start.

Freedom through systems isn’t just building things. It’s owning multiple income streams that don’t depend on you. Acquisitions can be a part of your portfolio for multiple income streams.

KEY TAKEAWAYS

• You can start smaller than you think: no investors, no search funds, no millions. just capital you have.

• Digital business acquisition is its own category: founders, apps, SaaS, platforms making $500–$10k/month are available at prices you can move on.

• Unlisted deals exist: most founders don’t advertise. the edge is finding them before listings through direct outreach, communities, relationships.

• Know what matters: profitability, tenure, revenue, retention, industry growth. due diligence isn’t optional.

• Observe first, then grow: first 30 days you understand. next 60 days you scale. don’t change everything at once.

• Systems beat complexity: a $8k/month business running cleanly is worth more than $20k/month that depends entirely on one person.

• Year one is learning: expect to say no way more often than yes. best investors build foundations, not exits.

• Diversification over flipping: some assets you hold for cash. others you improve and sell. the whole portfolio gets stronger.

Connect with Natia

1:1 Strategy Call: wa.me/natiakurdadze
Collaboration: natia@natiakurdadze.com
Follow her: x.com/natiakourdadze

You might be interested in reading these

• Don’t Spend Money You Don’t Have

• One Stream. One Investment. One Collapse. Unless you build a system

• I Inherited the Blueprint. Then I Forgot Everything.

• Two Generations. Similar Money

• They Move the Needle: Special SEO Edition with Natia Kurdadze

In this episode I sit down with guest, Omasan and we take opposite sides. Omasan treats debt as a tool, using arbitrage to grow wealth while servicing loans. I prioritize mental and financial freedom, keeping debt minimal and intentional.

Together we build a four step framework to help you decide what to do with your money right now.

What you will walk away with: how to sort your debt by interest rate and priority, when to invest instead of pay off, why credit card debt is non-negotiable to eliminate first, and how to pay yourself first even while in debt.

Your assignment:

Write down every debt you have.

The amount, the rate, the type.

Then ask: is this debt changing how I make decisions?

Two Paths to FIRE is hosted by Olamide Amosu.

New episodes weekly.

My mother had a simple rule: don’t spend money you don’t have.

not “avoid credit cards.” she was specific: the actual act of not spending what doesn’t exist yet.

I thought it was deprivation when i was young. turned out it was strategy.

She learned it watching her own family build generational wealth. She’d seen people lose businesses, lose homes, lose everything because they borrowed thinking they could repay. The banks had other plans. so she spent cash, delayed purchases until the money existed. refused to borrow for consumption.

This principle became the foundation for everything for me.

The thing that gets me is how universal it actually is. Growing up in a cash economy meant you didn’t have access to easy credit. Banks were selective, My mum knew bankers and saw how flexible their interest rates were when they wanted you to get credit, they offered credit as if it were a prize.

In credit economies (the US, the UK), the system flips. credit is everywhere, easy to access without any financial explanation or literacy. The cultural message is: buy now, pay later. build now, figure it out later.

The underlying danger is the same in both systems. Debt transfers power from you to the lender.

Whether you’re in Lagos or London, when you borrow money you can’t repay quickly, you’re giving someone else control over your future earnings, your assets, your options. that’s the trade-off nobody wants to say out loud.

My friend’s parents understood this. when they visited the US, they’d use their credit card but pay it off immediately: same day, at home: with cash from their account. no balance carried. no comfort with owing. they brought the cash economy mindset into a credit economy and stuck with it. that’s what mattered.

Waiting actually looks like this:

You want a $1,500 laptop for your business but you only have $500 saved. The wait principle says: build the remaining $1,000 first. if you save $250/month, that’s 4 months. Four months of waiting for a tool that will help you earn more. that’s not deprivation: that’s strategy. or my own example: travel. I wanted to travel internationally but couldn’t afford it on salary alone. so i waited built side income. saved aggressively for two years. then I could travel without debt. now it’s part of my lifestyle without the monthly payment stress.

The timeline depends on what you’re buying and why. a house might take years. an expensive dinner: that’s a week or two of passing.

debt isn’t equal though.

Bad debt funds consumption. credit cards for shopping. car loans for depreciating vehicles. lifestyle purchases. this debt works against you. you’re paying interest on something that loses value and that’s just math.

Good debt builds assets. a mortgage on real estate that appreciates. , a business loan that generates revenue. a student loan that increases your earning potential. Healthcare falls into this category as well, this debt can work for you. the asset or income it creates can outpace the interest you pay.

the difference is simple: does this debt build something that generates value, or does it fund something that depletes?

Most people reverse this. they take on massive debt for consumption (cars, clothes, status symbols) and not for assets that compound or grow.

my rule is: borrow only for things that build or an emergency. everything else? wait.

the real cost isn’t interest.

• when you carry bad debt, you’re not just paying interest. you’re paying with your options.

• debt is a tax on impatience. every dollar borrowed works against you for years. interest, stress, opportunity cost. the compound damage of money working for the bank instead of for you.

• debt stops you from taking risks.

• you can’t leave a job that doesn’t align with your values because you need the paycheck to service the debt.

• you can’t start a business.

• you can’t move cities.

• you’re locked in, dependent, stressed. that’s the part that got me. that’s what i saw.

  Subscribe now

most people misunderstand delayed gratification.

they think it means: don’t live your life (YOLO). don’t enjoy anything. that’s wrong.

I’m saying: be intentional about what you choose.

Most people increase spending the moment income increases. that’s the trap. that’s how you stay dependent, and this is called Lifestyle Inflation.

If you want freedom, you have to choose carefully. Find one thing you genuinely enjoy and will sacrifice other things for. for me, it’s travel. Now I pass on designer bags, expensive dinners, status symbols. but I invest in experiences and exploration. that’s my line in the sand.

If you’re living paycheck to paycheck buying everything, you can’t focus to build assets. but if you have discipline on lifestyle: if you’re intentional about what matters: you create space for real wealth to compound. that’s not deprivation. that’s design.

Generational wealth is fragile if it’s built on more debt than asset.

The generation my parents grew up in built their foundation first and was less focused on a flashy lifestyle, it was slower but the built the foundation first.

but it also meant: they had assets to transfer to the next generation. no inherited obligations. no financial stress passed down as inheritance.

when you transfer wealth without debt attached, you transfer actual freedom.

Freedom also looks like not owing anyone.

When you refuse bad debt, you’re buying the only thing money actually buys: options.

you can quit. you can take risks. you can invest aggressively. you can say no to bad deals. debt removes these options. it locks you into obligation.

Here’s what to do:

Task: Audit your current debt. not all of it: just one piece after the other.

Ask: does this build assets or fund consumption? is this debt working for me or against me?

if it’s against you, that’s where the work starts.

Stay tuned 🎙️

Tomorrow on the Two Paths To FIRE Podcast, I’m hosting a debate with a guest about one of the biggest money questions: Should you invest or pay off your debt first?

Listen to New Episode

It’s a nuance this post can’t fully cover because the answer depends on your debt type, your interest rate, and your timeline. We go deep into when borrowing makes sense, when it doesn’t, and how to think about the trade-off.

Also in This Series:

• One Stream. One Investment. One Collapse. Unless you build a system

• I Inherited the Blueprint. Then I Forgot Everything.

• Two Generations. Similar Money

For some it's quitting work tomorrow.

For others it's a number on a spreadsheet.

For some it's freedom from debt.

For others it's owning your time.

In this episode, Olamide sits down with Omasan to break down what Financial Independence, Retire Early actually means, beyond the buzzword, and why getting clear on your definition is the foundation everything else is built on.

Olamide shares her operating system: pay yourself first, automate before you spend, never make emotional decisions when the markets move. Omasan brings a different lens, a dual system of passive and active investing built on one core belief: you need to be an owner, not just a worker.

Together they share three rules that will change how you think about money.

Your floor, the minimum savings habit you keep no matter what.

Your pillow, the buffer that catches you when life happens. Your ceiling, the lifestyle cap that stops wealth from leaking out as fast as it comes in.

Your takeaway this week:
Write down your three money rules. The ones you'd follow on your worst week. If you can't name them, you don't have them yet.

Two Paths to FIRE is hosted by Olamide Amosu, Founder of Unusual Strategist.

New episodes weekly.

One of my five money values is Diversify Everything Income, Portfolio & Assets.

I inherited the foundation from my mother. In my previous post, I shared how I inherited it, lost it, and my reset to building my path. I have since crafted my personal finance and money values. This principle has defined how I build for the path of FREEDOM.

Diversification

Everyone knows diversification is smart. Almost not everyone does it because it requires admitting something uncomfortable:

If you work a job, your job controls your freedom. If you run a business, your market does. If you own one investment, one sector crash is your crisis.

I understood this early because I watched my mother build systems, not single bets. But I had to learn it through my own mistakes through running multiple businesses simultaneously, through watching one income source slow down and having others carry the load, through building redundancy because I’d seen what happens when you don’t.

Here’s what made diversification non-negotiable for me: I started my career as an entrepreneur. I was genuinely broke but I had options. I hustled across multiple income streams because I had to. Then I moved into corporate, and suddenly I had one paycheck. One employer. One future path that wasn’t mine to control.

I didn’t want to stay in corporate long-term. But I couldn’t leave without a plan. So I applied what I’d learned as an entrepreneur diversification, and knowledge inherited. I built income streams alongside my salary. I started investing aggressively in assets. The goal was clear: use diversification to build faster, accumulate assets, and create the freedom to leave.

Diversification gave me choices. It gave me control.

One income stream limits your freedom. One investment increases your risk if it fails.

Freedom isn’t about having money. It’s about having options. And options only come from distribution.

Two Types of Diversification

Most people think diversification means “own different stocks.” That’s incomplete.

Real diversification has two layers:

1. Income Diversification — Multiple sources that actively generate money. This is your portfolio career: multiple income streams, multiple ownerships, multiple ways to earn. It’s not scattered. It’s strategic.

2. Asset Diversification — Multiple asset classes that passively compound or provide backup income.

You need both. Here’s why and how.

Income Diversification: Multiple Revenue Streams

This is where you take control back.

What a single income stream looks like:

• One salary = one employer controls your schedule, growth, and future

• One business = one market can destroy it

• One consulting client = one person can leave

The Portfolio Career: What Income Diversification Actually Looks Like

The knowledge I inherited from my mother wasn’t framed like this. When I started my career, there was no name for what I was doing. But I had slowly been practicing portfolio career all along as an employee, a blogger, an importer, a photographer, a consultant. Multiple roles. Multiple income sources. Multiple ownerships.

I wasn’t following a framework. I was following what my mother modeled: don’t depend on one thing.

A portfolio career is a deliberate strategy where you build multiple income streams simultaneously, each with its own ownership, timeline, and outcome.

It looks like:

• Running a business while maintaining salary income

• Consulting for clients while investing in stocks and real estate

• Building a content platform while owning equity in other companies

• Selling courses, e-books, being an influencer.

• Multiple revenue sources, each generating cash flow or appreciation

• Control distributed across multiple bets instead of concentrated in one

The point isn’t to be scattered. It’s to be strategically redundant.

That’s the system I’m building.

What income diversification looks like:

Active Income (requires your time):

• Salary (short-term, most predictable but least control)

• Consulting (medium-term, more control, variable)

• Paid writing platforms (short-term, scalable)

• Content creation/influencer income (medium-term, builds audience)

• Building/freelancing for clients (medium-term, control + income)

Business Ownership (varies in time requirement):

• Bootstrap a business (high control, high time initially)

• Acquire or buy an existing business (faster scaling, less uncertainty)

• Own equity in other businesses (passive ownership, shared returns)

• Invest in small businesses needing capital (you become the bank, earn interest or equity)

• Monthly subscriptions from your product/service (recurring, predictable)

Investment Income (requires capital upfront):

• Dividends from stocks (short-term cash flow, long-term growth)

• Real estate rental income (medium-term, recurring monthly)

• Interest from savings or certificates of deposit (short-term, safe)

The point: When I moved from 50% to 70-90% salary investing, I didn’t just save aggressively. I built income from multiple sources. My consultancy. The tourism blog. Investment portfolios. The importation business. Sometimes five things running alongside the 9-5.

The moment one business outpaced my salary? Everything shifted. The system wasn’t dependent on my job anymore. One failure couldn’t collapse me. I had regained control.

Asset Diversification: Multiple Classes Over Different Timelines

Income streams provide cash flow. Assets provide security and compound growth.

Think about timeframe, not just category:

Short-Term Assets (1-3 years, stability + some growth):

• High-yield savings accounts (HYSA); liquid, accessible

• Certificates of deposit (CDs); guaranteed returns, locked in

• Bonds; medium returns, predictable

• Short-term dividend stocks; cash flow now, growth later

Medium-Term Assets (3-7 years, growth with some stability):

• ETFs & Mutual Funds; diversified exposure, professional management

• Dividend-yielding stocks; growth + income

• Short-term real estate (fix and flip, Short-term rental (Airbnb), Rental with near-term payoff)

• Your own business (building value to exit or scale)

Long-Term Assets (7+ years, maximum growth):

• Real estate (long-term appreciation, but provides rental income medium-term)

• Growth stocks (long-term holders like me, I don’t trade)

• Your business systems (compound in value over decades)

• Ownership stakes in growing companies (equity appreciation)

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Why This Builds FREEDOM & Generational Wealth

I build this way because I’ve learned something critical: one thing will fail.

Freedom isn’t about having more money. It’s about having options.

Options come from distribution.

If one income source slows, you have others. If one market crashes, you have exposure in another. If your job ends, three other income streams keep the system working. If stocks fail, you have real estate and business income. If one property market disappears, you have assets elsewhere.

One income stream means one point of failure. One boss, one market, one decision away from crisis.

Multiple income and assets mean you’re building a foundation that doesn’t require perfection. It requires distribution.

It’s protection. And protection is what creates real freedom.

Also, when your goal isn’t just personal wealth when it’s wealth that transfers and compounds across generations you can’t afford to be concentrated. You stop thinking like an individual trying to maximize one thing. You start thinking like a systems architect: What stands if one piece fails? What compounds if one piece succeeds? What actually transfers intact to the next generation?

Generational wealth requires redundancy. Not out of fear. Out of certainty that systems survive what individuals don’t.

The Work: Map Your System

Income: How many sources do you have? (Be honest “side hustle” counts only if it’s consistent)

Assets: What are you holding? When do they mature? What do they generate?

The gap: If your biggest income source disappeared today, would the system still work?

If the answer is no, You can start building NOW.

If the answer is yes, you’re building FREEDOM. What compounds. What creates freedom for the next generation.

That’s the principle. That’s the work.

Listen to Two Paths To FIRE Podcast

I break down FREEDOM further on the podcast dropping today.

Also in This Series:

• I Inherited the Blueprint. Then I Forgot Everything.

• Two Generations. Similar Money

Subscribe now

My mother was a single parent building wealth. She gave us something better than the pocket money we wanted growing up: a blueprint for how freedom actually works. No debt. Real assets. Consistency over time.

Then I moved to university and forgot it completely.

The Foundation

In her generation, talking about money wasn’t as common. But she made it normal anyway.

She’d sit with the family business numbers. She’d talk about her goals, her assets, what she was building. She spent less than she earned. She invested in everything she could. She talked about debt as the burden that reverses everything you build.

Being an only child to her mother, she’d inherited high expectations early. Those got passed to us. It felt strict because we were different, living in a world where other kids seemed free with money. We didn’t understand yet that freedom wasn’t what their pocket money bought. It was what could be sustained and access to options.

My first real business education came from being close to the family business. I saw how she made decisions. Fast, diligent, strategic. I watched her build wealth through consistency, not shortcuts. Assets were key.

How I Lost It

I moved abroad for university as a teenager. It felt like freedom.

The world was massive. I wasn’t protected anymore. Or so I thought. What I didn’t realize was that my mother had been protecting me by not exposing me to the financial system designed to trap you.

The moment I got to university, financial institutions handed me opportunities. Credit cards. Overdrafts. They sold it like free money to someone with no guardrails and no industry knowledge. Everyone was doing the same. Our entire lives became about spending as teenagers.

I thought I knew what I was getting into. I was wrong.

Over time, the credit card bills stacked. The overdraft spiraled. The burden my mother had always warned me about was suddenly mine. I was in debt. In shame. I’d bitten off more than I could chew.

I’d forgotten everything she taught me.

Returned to My Foundational Knowledge

1. The Reset

When I started working, the first thing I did was clear all the debt. Then I went back to foundational knowledge. No debt first. Then build assets.

I was very resourceful. At 19, I’d started importing gadget accessories from China to the UK, selling online in Nigeria. Now I applied that same resourcefulness to wealth building.

2. The Foundation

I started saving aggressively. 50% of my first paycheck went straight into stock accounts. Fixed deposits. Certificates of deposit. Things I’d first heard about from my mother’s conversations with bankers as a teenager.

Two years into working my 9-5, I saved enough to buy my first real asset: land. I asked my mother if she’d help me buy it. She said wait. I kept searching. When the timing was right, I moved.

3. The Acceleration

I found a circle of friends who were serious about money. Not shame. Not secrecy. Just real conversation about building wealth together.

My friends and I looked for small businesses that needed capital. We’d invest for a percentage of the profit. We started multiple businesses simultaneously: my consultancy, the tourism blog, investment portfolios, the importation business. Sometimes I was running five businesses alongside the 9-5. Each had separate accounts. Each had separate financial goals.

Here’s what shifted everything: the other businesses started generating more than my paycheck. That’s when I moved to investing 70-90% of my salary automatically. The paycheck became the safety net. Everything else went into ETFs, investment accounts, assets. This forced discipline. I couldn’t spend what I didn’t see. The money moved before I could touch it.

4. The Return

Over time, I scaled back some businesses. Kept only what could stand the test of time. Then I looked back.

I realized I’d been following my mother’s blueprint the entire time. I just had to find my way back to it. Build assets. Consistency over time. Multiple income streams so one failure doesn’t collapse everything. Invest aggressively. Talk about money without shame.

The blueprint was always there. I just had to lose it to find it again.

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Why this matters: Financial independence isn’t about being rich. It’s about freedom. It’s about options. It’s about waking up and making decisions because you want to, not because you’re afraid.

When you understand how wealth actually builds through systems, through consistency, through assets you stop chasing the lottery ticket. You stop waiting for the big break. You start building.

I’m building so I can choose my life. Not let financial fear choose it for me.

Once you see how it works, you can’t unsee it. You realize:

The shame around money is a barrier, not a character flaw. Most people don’t know how wealth actually compounds. The generation before us knew something we’re having to relearn. Breaking the silence around money is the first step to breaking the cycle.

We need to stop being ashamed of ambition around money.

We need to break the silence that keeps people trapped.

We need to see money conversations modeled, not as greed, but as strategy. Not as shameful, but as foundational.

The generation before us understood something. We’re relearning it. And the generation after us needs to see us do it.

Listen: Episode 2 of my new Two Paths to FIRE podcast is live on Spotify.

In this episode, Olamide shares the personal origin story behind Two Paths to FIRE. From watching her mother build wealth to falling into credit card debt as a teenager in the UK, to climbing corporate ladder and realizing that a fancy title doesn't protect you from the system, this is where the why begins.

Olamide shares the money values she inherited, the financial pitfalls that followed her into adulthood, and the moment she decided to reclaim her path: saving early, investing intentionally, and building passive income so her money works while she sleeps.

In this episode:

• The early wealth education most of us never got and how Olamide got it at 12

• The UK credit card trap and what it cost her beyond money

• Why a corporate title doesn't equal financial safety

• The fear she's solving with every financial decision she makes

• What FIRE actually means beyond the number

Your homework this week:Write down your one WHY FIRE. The one fear you're trying to solve with your money.

Two Paths to FIRE is hosted by Olamide Amosu, Founder of Unusual Strategist.

New episodes weekly.

I grew up watching my mother build wealth. It was my first lesson in what determined, strategic wealth-building actually looks like.

You consume enough “get rich quick” advice, or the wall street advice of simply trading stocks and “boom” you are wealthy and you could be convinced that wealth is built on momentum, luck, or a single big bet.

But watching my mother for decades taught me something different.

She inherited a business and money habits from her own mother. She understood that inheritance wasn’t an endpoint. It was a foundation to build from.

She had a system. A deliberate, specific, tested system that built real wealth over time.

She inherited a foundation

My mother started with what she had: a business and generational wealth lessons.

The business gave her cash flow. The lesson gave her something more valuable. A blueprint for how wealth actually compounds.

She set specific financial goals. Exact ones: “I will own X properties. I will have rental income of Y. I will have exposure across Z markets.” She wrote them down. She tracked them. She spoke about them, researched and She executed.

Her hierarchy was always clear.

No debt, first. This wasn’t deprivation. It was foundational. Debt works against compounding. You can’t build on quicksand.

Build from what you have, second. Every dollar had a purpose: go toward an asset, cover living expenses, or remain available for opportunity. No spare cash sitting idle. No lifestyle inflation creeping in.

Then real assets. Properties for rental income before a property to live in. Land. Businesses. Financial markets. Global exposure. Never concentrated in one place.

She was strategic about spending. She spent cash, not credit. She delayed big purchases. Her own home. Until the foundation was solid. She reinvested gains instead of upgrading.

This wasn’t scarcity. It was intentionality.

Every choice moved toward one thing: building a system that doesn’t collapse.

The five principles that compound

She understood something fundamental: one business is fragile. One income stream can disappear.

So she built beyond it. She built a diversified foundation where the business was just one part of a larger system.

Here’s what that looked like:

• No debt while building. Debt is a tax, and It reverses compounding.

• Real assets beyond one source. Land, property, diversified investments generate wealth independent of any single stream.

• Intentional spending. Every dollar has a direction. Cash culture means your spending reflects your priorities. Credit culture means spending reflects temptation.

• Specific, measurable goals. Not “I want to be wealthy.” But “I own 5 properties. I have $X in rental income. My assets are diversified across Y markets.”

• Diversification at every level. Assets (real estate, businesses, financial markets). Multiple income streams. Never dependent on one outcome.

This wasn’t just about money. It was about security. Independence. The ability to make decisions free from desperation.

Generational wealth is a system, not a moment

Most wealth advice treats wealth-building like a transaction. A single decision. A moment where everything changes.

Quit your job. Start a business. Make one investment. Hit your number.

But watching my mother taught me something else: generational wealth isn’t built in moments. It’s built in systems.

She didn’t call it anything. She just did it. Year after year. Asset by asset. Goal by goal. Until the foundation was unshakeable.

My mother built what she can transfer to the next generation. Not through shortcuts. Not through luck but hardwork. Through systematic, deliberate choices made over time.

The system works because it’s based on how wealth actually builds. Not how it’s described in quick tips, but how it compounds in reality.

So, what am I actually building?

This month I’m exploring what it means to build wealth deliberately. Not just to retire early, but to own your time. To build something that lasts. To think in terms of assets instead of income. To think generationally.

I have been building and recording podcasts about my personal finance journey over the past couple of months.

Two Paths to FIRE is a podcast about how wealth actually builds. Not the abbreviated version. Not the tips and tricks. The full system.

I’m hosting real conversations with friends and people I know about money, assets, systems, and what it takes to own your freedom. Our views might not always align. They’re mine, and theirs. But we share something fundamental: a commitment to financial freedom and building wealth deliberately.

Episode 1 is the introduction to the podcast. Why I’m doing this, what we’ll explore, and what to expect in the conversations ahead.

Listen on Spotify

Listen on Spotify | Subscribe for weekly episodes

Next week: How I applied this system. The specific choices, the investments, the moments that made the framework real.

Two Paths to FIRE is a podcast about building net worth that actually gives you back your time. Time with your family. Time to pursue what you love. Time to choose.

Hosted by Olamide Amosu, this show is built on real stories, honest strategies, and two distinct philosophies on what Financial Independence actually looks like and how to get there on your own terms.

Whether you're just starting your FIRE journey, deep in the numbers, or questioning whether the conventional path is even right for you, this is your space to think differently about money and your future.

New episodes weekly. Subscribe so you don't miss one.

You built your AI product with five features. You thought you were covering all the bases. You shipped to 50 beta users. Three months later, the data tells a story: good engagement on Feature 1. Dead silence on Features 2-5. Users show up once, poke around, and leave.

You have an MVP problem. You’ve been calling it a product problem.

THE MVP TRAP FOR AI

An MVP (Minimum Viable Product) for traditional software is sensible. Ship the minimum set of features that lets users experience your core value, get feedback, iterate. It’s efficient. It spreads resources thin but strategically.

But for AI products, an MVP is a trap.

Here’s why: most of your product is not your competitive advantage. Your AI tool probably does five things: summarize, generate, retrieve, classify, recommend. One of those is what makes you different from other AI tools in your category.

MVP thinking says: ship all five, see what sticks.

MLP thinking says: design a complete experience around that one differentiator, one that feels made for your specific user.

Two very different approaches.

WHAT MLP ACTUALLY MEANS FOR AI

MLP (Minimum Lovable Product) isn’t “fewer features.” It’s a complete, intentional experience designed so your first user feels like you built this for them specifically.

That means:

Your core differentiator is there (the feature that makes you different).

But also: emotional safety in how it works. Belonging if there’s community. Visible progress so they know they’re winning. Ruthless scope so nothing dilutes the core ritual. And metrics that measure whether it actually feels “made for me” - not just engagement, but emotional resonance.

Here’s what this looks like in practice:

i) MVP approach: Ship the code summarizer, the bug detector, the documentation generator, the test writer, the refactoring assistant. Measure engagement across all five. Optimize each one.

ii) MLP approach: Ship the code summarizer, but make it the complete experience. It’s accurate enough to trust (emotional safety). Show the engineer their streaks, milestones, improvements week over week (visible progress). If there’s a community layer, make it peers with the same goal (belonging). Kill anything that doesn’t serve the core experience. Then measure: do they feel like this was built for them? Do they come back daily? Do they show their team?

If yes: you have an MLP. Your core differentiator works in context.

If no: you need to redesign the experience around it, not add more features.

WHAT MOST FOUNDERS MISS

They miss designing for your specific first user.

You probably know who your first user is. But knowing and designing for are different things.

Designing for means: What does emotional safety look like for an engineer? (Accuracy. Speed. No judgment.)

What does belonging mean? (Peers, not just a tool.)

What does visible progress feel like? (Streaks, metrics, improvements they can point to.)

What can you cut without breaking the core? (Everything that doesn’t serve the ritual.)

This is where you let Claude do the work.

Take your product brief. Add your customer data: who they are, what they’re trying to do, what they’ve tried before that didn’t work. Add the pain point (what would change if they had your solution?). Add the emotional context (what do they need to feel safe, seen, and successful?).

Then ask Claude: Based on this brief plus these users plus this emotional context, what is the complete experience we should design?

What’s the one core differentiator plus the ecosystem that makes it feel made for them?

Claude will help you design an experience, not just a feature set.

THE GTM LOOP THAT WORKS WITH MLP

Remember the framework: Who succeeds first. Where they already talk. Message the outcome. Feedback loop.

MVP breaks this loop because you’re testing with five half-features and 50 users. Too much noise. Can’t see signal.

MLP makes the loop real.

Your “who succeeds first” uses your core differentiator daily and feels like you designed it for them. Your “where they already talk” is where people discuss that specific pain point, and you’re present there, not trying to build awareness. Your “message” is the outcome of that complete experience: what changes in their day, how they feel, not a feature list.

And the feedback loop? It’s clean. Retention on one experience. Daily usage. Share rate. Do they tell others? Do they feel seen?

That’s signal. That’s data that tells you whether you have product-market signal or whether you need to redesign.

THE RETENTION TEST THAT MVP MISSES

MVP measures: Did they try it?

MLP measures: Did they come back, feeling like it was made for them?

For AI products, the second one is everything.

An engineer tries your code completion once. It’s okay. They close the tab. That’s MVP feedback.

An engineer uses your code completion 47 times in a week. They’ve configured it for their style. It shows them their improvement. Their team asks how they’re shipping so fast. They feel like you understood exactly how they work. That’s MLP signal.

One tells you people are interested. The other tells you people feel seen.

THE THREE-QUESTION TEST BEFORE YOU SHIP

1. Who is the one user this is designed for, and what do they need to feel? (Safe, seen, successful)

2. What is the one core feature that solves their problem?

3. What complete experience do I need to build around that feature? (Emotional safety, progress visibility, community if relevant, ruthless scope) so they feel like I designed this for them specifically.

If you can't answer all three with conviction, you don't have an MLP yet.

BUILD YOUR MLP FOR YOUR AI PRODUCT WITH THE 4-PHASE PROCESS

Phase 1: Define Your Product What’s your differentiator? What problem does it solve? Why is it different?

Phase 2: Identify Your Specific First User Not a demographic. A person doing a specific task. What’s their pain point? What have they tried before?

Phase 3: Design the Complete Experience Emotional safety. Belonging. Visible progress. Ruthless scope. What’s the ecosystem around your core feature?

Phase 4: Measure “Made for Me” How will they signal that this was built for them? Daily usage? Share rate? Team adoption? Define it before you ship.

Free MLP template

I’ve built a free MLP Template that walks you through designing a complete experience for your specific user. It’s designed to work directly with Claude: fill in your product brief, customer data, and emotional context, and Claude helps you design the full MLP.

No sign-up. No gatekeeping. Just a tool to get clarity before you build.

Download the MLP Template

If you fill it in and realize your complete experience isn’t clear, or you’re not sure what “made for me” means for your specific user, that’s the moment to pressure-test it before you ship.

Need help pressure-testing your MLP? Book a 90-min strategy session

Subscribe now

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• You Shipped the product. You skipped the GTM

After I pivoted from building Kabilara to building personalized Health Codes, something shifted.

Women weren’t asking me to do it for them.

They were asking: How do I do this myself?

So I documented the entire system. Here’s the step-by-step blueprint to build your own personalized Health Code using Claude Code.

What You’ll Build

A personalized hormonal health system that remembers everything about your body, your cycle, your food, your lifestyle and gives you specific, targeted guidance based on your exact hormonal pattern.

Not a diet plan. Not generic wellness advice. A living document that grows with you.

What You Need

• A Claude account (claude.ai) or Chatgpt/Gemini

• Claude Code installed (code.claude.ai) or Claude Cowork

• A folder on your computer for your Health Code

• 30 to 60 minutes for your first session

• Honesty about your symptoms, diet, and lifestyle

The 6 Phases

Phase 1: Setup (Day 1 — 15 minutes)

Create a folder on your computer called Your-Name-Health-Code. Open Claude Code or Claude Cowork in that folder. Ask Claude:

Create a memory folder with a MEMORY.md index file 
and a health profile file for me

This allows Claude to remember you between sessions. Without memory files, every conversation starts from scratch.

Phase 2: Your Initial Diagnosis (Day 1 — 30 to 60 minutes)

This is the foundation. Be specific.

Share your symptoms:

• Where do you carry weight? Has this changed?

• Do you crash 2-3 hours after eating?

• Are you tired in the mornings even after sleeping?

• Do you get brain fog on days you don’t exercise?

• How long is your cycle? How heavy is your flow?

• Do you have PMS, and has it worsened over time?

• Do you have diagnosed conditions (fibroids, endometriosis, PMOS)?

• Do you feel irritable or shaky when you skip meals?

• Do you bloat after eating?

• Do you wake between 2-4am? Do you struggle to fall asleep?

Share your sleep and wake times:

Cortisol follows your circadian rhythm. Consistent sleep timing is structural, not optional.

Share your diet:

Tell Claude what you actually eat not what you aim to eat. Include cultural foods, cooking methods, what you drink, morning rituals.

Share your exercise routine:

What you do, how often, whether you train fasted, how intense, how you feel during and after.

Share your lifestyle context:

Work schedule, prayer times, fasting practices, stress levels, family commitments. These are the framework your protocol gets built inside.

Claude will identify your hormonal pattern usually cortisol, insulin, estrogen, progesterone, or thyroid (most women are a combination).

Phase 3: Building Your Protocol (Days 1-7)

Ask Claude:

Map my food protocol to my actual foods, not generic recommendations.
Which of my existing foods are already supporting my pattern?
What's missing?

Then ask for your timing framework:

When should I eat my first meal?
When should I train and what should I eat before?
When should I walk and why?
What should my evening wind-down look like?

Phase 4: Create Your Reference Documents

Ask Claude:

Generate a PDF reference document with my hormonal pattern, 
weekly exercise schedule, daily timing, meals, and non-negotiables

Save this to your phone. It’s your portable protocol.

Phase 5: Daily Practice

• Log your meals daily

• Check in after training

• Track your cycle phases (menstrual, follicular, ovulation, luteal need different support)

• Update your memory files as things evolve

Phase 6: Continue Building

Keep logging and refining your protocol. Use it as a training document—your Health Code evolves as you do. The more data you input, the more accurate your guidance becomes.

Core Principles

These run through every session and recommendation:

• Location is diagnosis. Where you store fat tells you which hormone is disrupted.

• Cortisol is always upstream. Fix cortisol first; everything else cascades.

• Food is the first intervention. No supplements replace foundational nutrition.

• Your protocol must fit your actual life. Your culture, your schedule, your foods it all matters.

• Consistency beats perfection. 12 weeks of showing up beats one perfect week.

What to Expect: Timeline for Results

^{Disclaimer: The Health Code is a lifestyle-based system. It is not a replacement for medical care. The Health Code works alongside medical care, not instead of it. Many women find that consistent dietary and lifestyle changes produce measurable improvements in their symptoms and lab markers, but those changes should be monitored by a qualified practitioner, not self-managed in isolation. If your symptoms are severe, worsening, or include heavy bleeding, significant pain, or unexplained weight changes, seek medical evaluation first.}

What Shifted for Me

I’ve always done consistent strength training (3 days a week). Before the Health Code, I was stacking that with a lot of cardio: running, cycling, Zumba. My body was in constant high-intensity mode.

Now? I kept the strength training (that foundation is solid), but I stopped the excessive cardio. Instead of running, cycling, and Zumba on top of strength days, I’m doing yoga and pilates with intentional level 2 cardio: one run a week, walking regularly. I frontload protein on strength training days, eat before every workout, and prioritize sleep quality with breathing work.

I also started regulating which teas I drink at specific times. Ginger turmeric in the mornings, peppermint after lunch, chamomile before sleeping. They all function differently, and timing them right becomes part of your protocol, not a random choice.

The brain fog that used to hit every morning is gone.

I’m not doing less. I’m doing smarter.

Learn from the Best

Substack Pages & Communities That Shaped This Work

I’ve learned from women doing exceptional work in women’s health, hormones, fitness, and nutrition. If you’re building your own Health Code, these are the Substacks that continue to shape how I think about hormonal health.

Understanding Hormones & Signals

• — Shares how to understand whats going on in your body, energy, hormones, blood sugar, gut. Root-cause approach.

• — Shares about Hormonal health, cycle syncing, and what your body is actually trying to tell you

• — Shares about Hormonal health and PCOS insights

• — Shares science backed research and practical tips on Hormones, understanding each signal and sign

• — Shares about women balance hormones, feel strong, and thrive during pregnancy, postpartum, perimenopause and menopause

• — Shares about Women’s health and Wellness (Fetilitiy)

• — Shares functional medicine perspective on women’s health

Training Smart for Your Cycle

• — Shares about overall fitness and wellness for women. Training plans, eating, growing muscle, easy to follow

• — Shares about sports and science-backed strength training for perimenopause, menopause, post-menopause.

• — Shares about longevity fitness tips, backed by sports medicine.

Nutrition & Eating Well

• — Shares Nutrition tips grounded in real eating

• — Shares general wellness, fitness, eating and lifestyle

• - Shares about diet regulations and reset for women’s health

• — Shares meal prep and Anti-inflammatory eating to heal guts and hormones

• — Shares overall wellness, food and lifestyle for women.

• — Shares Nutrition and inflammatory drink receipes

• — Shares Women’s health and wellness

Ready to Build?

If you have hormonal imbalance, fibroids, PMOS, endometriosis, worsening PMS, or cycle-dependent symptoms this is for you.

Download the complete guide: How to Build Your Health Code (Free PDF)

Ready to go deeper? Book a 90-minute Health Code Strategy Session

I’m documenting women’s journeys as they build theirs. Reply to this post if you want to feature yours.

I’ve been living with hormonal imbalance for years. Not as a theory. As a lived reality. The fatigue. The unpredictability. The frustration of doctors who didn’t have answers.

And I watched it happen to every woman in my circle. Different diagnoses, some had fibroids like me, some had PCOS now (PMOS), some had endometriosis, but the same feeling: alone, confused, unsure how to navigate their own bodies.

For years, I pondered: What if there was a space where women like us could understand our bodies? That question became Kabilara. “My community” in Swahili. A platform to help women with hormonal imbalance get the clarity they needed, and build community.

THE BUILDING

I managed product teams previously in Tech. I understand product architecture, user flows, iteration cycles.

I used Claude Code and Lovable as my technical partner. And shipped the MLP. The product worked. The code was solid. The interface was clean.

I had the vision. I had the lived experience of hormonal struggle.

Everything should have worked.

THE MOMENT EVERYTHING CHANGED

I put Kabilara in front of the women I was building it for.

One woman logged her cycle data. Another joined one of the chat rooms. A third set up her profile and 1 daily strike.

Then they came back with the same question: “Can you just tell me what to do?”

Not: “Is this interface confusing?” Not: “Does the tracking work?”

Just: “Can you hold my hand and tell me I’m not alone? Can you tell me what actually helped you?”

One woman said something that landed differently: “I don’t need another app tracking my cycle. I need someone to tell me I’m not alone and that there’s a way forward.”

I had built the solution to the wrong problem.

I had all the skills to build a product. I had none of the awareness to know they didn’t want one.

THE REALIZATION

I’d romanticized this as a technology problem. If I build the right platform, women will understand their symptoms better.

But the real problem wasn’t information access. It was isolation. It was uncertainty. It was not knowing if what they were experiencing was normal.

They needed someone who had lived it to say: “Yes, this happened to me too. Here’s what helped. Here’s what I learned.”

Technology can’t do that. A product can’t do that. Only a human can do that.

THE PIVOT

Instead of shelving everything, I took what I learned and built something different.

I built a personalized Health Code system. Not a product. Not an MLP. But a deeply personal protocol custom-built for each woman’s hormonal pattern, her foods, her lifestyle, her cycle, her life.

For each woman, I’d gather everything: her symptoms, her diet, her exercise history, her preferred foods, her cycle patterns, her energy crashes, her goals.

Then Claude and I would map it against the hormonal patterns: cortisol, progesterone, estrogen, insulin, and build a protocol entirely from food and lifestyle.

No supplements. No medication. Just real changes that address the upstream cause.

What makes it work is that it remembers everything. Every meal she logs. Every training session. Every time she feels depleted. Every phase of her cycle. It builds context over weeks and gives guidance specific to her, not generic advice.

A client with endometriosis got it. Within one session, the Health Code had mapped her symptoms against the hormonal framework for endometriosis. It explained why high-intensity training during her menstrual phase amplifies her pain.

So I pivoted completely. I stopped building a product and started offering personalized Health Codes.

I stopped trying to scale and started showing up.

WHAT HAPPENED

There were honest questions that had answers in eating patterns, exercise patterns, sleep routines and more.

Holding their hand through each phase of their cycle. Explaining why they crash on certain foods, and using the balanced training with hormonal health.

THREE LESSONS

1. Building is easy. Listening is hard.

You can have all the skills, the product sense, the technical ability, the lived experience and still miss what people actually need because you’re too focused on what you think they need.

2. The gap nobody talks about is the listening gap, not the credential gap.

Everyone assumes the gap is credentials. If only I had a medical co-founder, Kabilara would work.

3. Sometimes the best pivot isn’t a bigger team or better technology. It’s the courage to stop building and start listening.

Your Health Code is waiting. A protocol built entirely around you, your symptoms, your foods, your life, your cycle.

If you’re ready to stop guessing and start understanding your hormonal imbalance symptoms, reply to this post or send me a message.

The next post will be sharing how to build your own Health code for free with Claude.

Read more about the Health Code

• How to build the Health Code with Claude

Nine months ago, I was brought in to run the go-to-market for an Edtech.

The product was genuinely good. They had launched a set of AI-focused courses, with the whole school built around one thing: teaching people how to actually use AI to build. Not theory, not watching someone else do it, but shipping real projects with the tools in front of them. They had spent months building the curriculum, and everyone who saw it was impressed.

Then someone asked the question nobody had answered: who do we launch to first?

The room went quiet in a way that told me everything.

They had a product. They did not have a GTM. And in the four weeks before launch, they were about to find out how expensive that gap is.

Here is the thing about AI products that most founders miss.

With traditional software, the wrong early user is annoying. They churn. They leave a bad review. You move on.

With an AI product, the wrong early user does something worse. They generate bad outputs, because their use case sits at the edge of what the product was built to handle, and because they expected something the product was never designed to do. Then they don’t blame themselves. They blame the product. And they tell people.

Your first ten users are not just customers. They are your proof of concept.

And proof of concept means something specific here. It is not the demo that wows a room, and it is not a slide that says the technology works. It is a small group of real people using the product in their own context, with no one beside them to help, and walking away with a result they did not have before. That is the only proof that counts, because it is the proof every future customer is quietly looking for: did this actually work for someone like me?

Get those first users right and their success becomes the evidence that sells everyone after them. Get them wrong and the failure becomes the evidence too.

The wrong ten will undo six months of building in six weeks of word of mouth.

This is why the standard GTM playbook breaks down for AI products. “Target the broadest addressable market and filter down” is exactly backwards.

You need to start narrow enough that your first users are almost guaranteed to succeed, and then let those successes do the expanding for you.

For the Edtech, that meant ignoring the instinct to go wide (every learner, every subject, every level) and asking one harder question: who will get the best possible result from these courses on day one, with zero hand-holding, and tell someone about it?

The answer turned out to be a very specific person. Not “students.” Not even “adult learners.” A mid-career professional, already self-directed, who had a specific skill gap they needed to close before a specific deadline, and who had already failed at the traditional format (in-person courses, static video modules) at least once.

That person was not the biggest segment. But they were the right first user. They came in with clear intent. They got clear results. And they talked.

The framework I used, and now use for every AI product I help launch, including my own, has four parts.

1. Who succeeds first. Not who has the broadest need. Who will generate the best output from your AI immediately, without support, and have a result worth sharing. Start there. Expand after you have proof.

2. Where they already talk about the problem. Not a target demographic. A specific place: a Slack community, a WhatsApp community, Substack community, a LinkedIn thread, a subreddit, a newsletter comments section, where the right first user is already naming the problem your product solves. You are not building awareness. You are finding the conversation that already exists and entering it with a solution.

3. The message that names the outcome. Not what the AI does. What the user walks away with. “An AI that personalizes your learning path” is a feature. “Close a skill gap in four weeks, without a fixed schedule, without sitting through content you already know” is an outcome. One of these makes someone forward an email. The other makes them close a tab.

4. The feedback loop & Data. How you know the first users are succeeding before you scale. For the Edtech, this was simple: did they complete the first course, and did they build any MVPs and did they share it? Completion plus building an MVP and sharing was the signal. If that was not happening, the product was not ready for more users, not because the content was broken, but because the experience was not good enough yet to generate the right word of mouth. The feedback is in the data you generated from the experience and what you want.

I spent 15 years in GTM strategy across Tech, for products used by millions of people. I applied a version of this framework every time. The inputs were different. The logic was the same.

The difference with AI products is that the stakes of getting the first user wrong are higher. The upside of getting them right, a small group of people who succeed visibly and talk loudly, is also higher.

You don’t need a big launch. You need the right first ten.

Figure out who succeeds first. Everything else follows from that.

If you are building an AI product, or helping someone launch one, and you are not sure who your right first user is, that is the question to answer before anything else.

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If you already have an answer, reply and tell me. I want to know what criteria you used to get there. If you are still figuring it out, that is what the session is for.

I have three spots open for a 90-minute GTM strategy session. We will map your first user, your entry point, and your feedback loop.

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Continue reading about GTM for AI Products

• GTM Gets Your Users and Marketing Keeps Them

After leaving that team behind, I started building alone.

And I had to figure out how one person could do what used to take multiple teams.

AI was the answer. But not in the way most people mean when they say that.

Here is what I have actually learned.

1. Most people brief AI like a task manager. That is why the output is generic.

The prompt “write me a LinkedIn post about my product” will always produce mediocre output. Not because AI is bad. Because the brief is bad. A strategist does not hand a copywriter a topic. She hands them a positioning framework, a target reader, a tone of voice, and a specific angle. AI is no different. When I started briefing it like a strategist with context, constraints, and a clear point of view everything changed.

2. AI defaults to the average. You have to interrupt that.

Every AI model has been trained on billions of pieces of content. Its default is the middle of all of it. That is why so much AI writing sounds like everyone else. The prompt is the only thing that pulls it off the mean. Specificity does it. Voice signals do it. Strategic framing does it. Without those, you get polished generic output every time. As a strategist, feed the prompt with more about you, this guides the output.

3. Your voice is a skill, not a personality trait.

I spent a long time thinking voice was something you either had or you did not. What I have learned is that voice is a set of rules. Sentence length. What you refuse to say. How you open. Where you place the insight. Once I documented my own rules, I could brief AI to follow them. That changed everything about how I write and how fast I write.

4. The prompt is the thinking. The output is just execution.

When I write a strong prompt I have already done the hard strategic work. I know what I am saying, who I am saying it to, and why it matters. AI just puts it into language. This is why people who outsource the thinking to AI always sound like AI. The thinking is still yours. The prompt is where you do it.

5. One person can do the work of eight. But only with systems, not shortcuts.

years in, I have a full content and marketing operation running with one person me. Not because AI is magic. Because I built real systems around it. Prompt libraries. Voice documents. Structural frameworks for every content type I create. Every time something worked, I kept it.

That is what I have been building for over two years. Today I am making it available.

The Unusual Strategist Bundle is open.

The AI Prompt Pack gives you 30 of the prompts I actually use across GTM and Launch, Brand Voice, Competitive Intelligence, Strategic Thinking, and Marketing Ops. Each one is built for output you can use the same day, not a starting point that needs an hour of editing. Plus two bonus guides: How to Brief AI Like a Strategist, and the Prompt Customization Guide.

The Writing Templates give you five post formats built around my own voice rules: The Bold Opinion Post, The How-I-Did-It Post, The Tool Breakdown, The Roundup, and The Launch Post. Each template includes structure, headline formulas, and the writing prompts that pull the story out of you. Plus the Unusual Strategist Voice Rules cheat sheet.

Use the prompts to think. Use the templates to write. That is the system.

The bundle is $47 for subscribers.

Both products. One price. No upsell waiting on the other side.

Use code EARLYBIRD at checkout.

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I built this because I spent years being the best strategic thinker in every room except my own.

Own Your Growth.

Olamide

The first time I priced my own offers, I low-balled it.

Not because I didn’t know better. I had spent years building pricing models competitive analysis, value-based frameworks, willingness-to-pay research across markets. In tech & retail, I never set a price on a hunch. I had the data, the methodology, the confidence.

Alone at my desk, building something of my own, I looked at what I was worth and shaved it down anyway.

Doubt will do that. The transition will do that.

In 15 years of leading product launches across companies, I never launched without a hypothesis. Never spent without a framework. Never moved without knowing what success looks like.

Every campaign had a brief. Every brief had an objective. Every objective had a metric.

Then I started my own business. And I guessed constantly.

The transition does something to your rhythm. In corporate, the structure is already there the approval gates, the briefs, the reviews. You move inside a system that forces rigour even when you don’t feel like it. When you step out, that system disappears overnight. And without it, I found myself jumping with my heart first. I had data but not the complete picture of my ideal customer. I built based on my own problem statement and hoped it was someone else’s too. I priced based on what I thought someone would pay, not what the value commanded.

It took me longer than I’d like to admit to realise I had abandoned every framework that made me a strong GTM leader, and replaced it with the one thing I’d always dismissed: intuition dressed up as strategy.

When I finally applied the same rigour to my own business that I applied to every product I’d ever launched, with AI as my operations partner, the guessing stopped.

I mapped my ICP the way I would map a target segment and found that the woman I was building for was not the woman I was speaking to. Two different people. One was a guess.

I built my content system the way I would build a campaign architecture and stopped posting because I felt like it and started publishing because the data told me what was working and the calendar held me accountable to it.

I positioned my offers the way I would position a product launch and priced them at what the value commanded, not what the doubt permitted.

The difference wasn’t the AI. The AI was just the team.

The difference was deciding to stop treating my own business as the thing that deserved less than my best thinking.

What I lost in those months of vibing it was not just revenue. It was time.

Every month I spent guessing was a month I was not connecting with my actual audience. Not building the relationship that compounds. Not creating the proof that brings the next person in.

You built the skills. You have the frameworks. The only question is whether you are ready to point them at yourself before another quarter passes.

What is the one decision in your business you have been making on instinct that deserves a proper brief? Reply and tell me. I read every one.

I have been building something for this.

The AI Prompt Pack the exact prompts I use to run my GTM strategy, content system, competitive research, and brand voice. Built from 15 years of doing this at scale. Packaged for the woman who wants to stop guessing and start executing.

It launches June 1st.

If you want first access before it goes wide, reply to this post. I will send it to you directly before it is anywhere else.

I have an accountability partner. We check in monthly. And I’ll be honest with you some of those calls are the most uncomfortable conversations I have all month.

Not because she’s harsh. Because she remembers what I said I was going to do. And because we actually talk about it.

That’s the whole point.

Most entrepreneurs treat accountability like a support group or a cheerleading session. You show up, share what’s hard, and not have real conversations on the path forward.

Or they treat it like a solo audit you prep your data, you report, you leave.

Neither one works.

Here’s what that looks like for me: Before every monthly check-in, I spend thirty minutes setting clear milestones for the month ahead. What do I want to ship? What’s the minimum viable progress? What am I committed to, and what am I saying no to? That’s the solo part. That’s mine to do.

Then we meet. And it’s not an interrogation. It’s a conversation. We discuss what actually shipped last month. What stalled and why. What I’m learning. What surprised me.

And then this is the part that changes everything we bounce ideas. She asks questions I haven’t asked myself. I get perspective from someone who’s been through the same transition. We problem-solve together.

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This is the thing corporate trained us to do and entrepreneurship quietly talks us out of. In a company, you had peers and leaders. You had retrospectives built into the rhythm. You didn’t build alone. The structure forced collaboration.

When you work for yourself, you have to create that structure intentionally. And most women who leave corporate and build their own thing stop looking for it. They convince themselves solo is safer. Or they find “accountability” that’s just cheerleading with no teeth.

What they’re actually missing is this: someone on the same journey who you trust enough to be honest with. Someone who knows what discipline looks like because they’re doing it too.

Your accountability partner cannot do their job if you show up unprepared.

The collaboration only works if you’ve done the solo work first. The solo work only matters if you’re measuring against something real milestones, not just hopes. And the milestones only become actionable if you’re discussing them with someone who gets what you’re building.

This is what operating like a strategist in your own business looks like. Not hustle culture. Not isolation. A rhythm. A commitment to yourself. And a person who respects you enough to have the real conversation.

Find that person. Show up prepared. And let the conversation be honest where you can actually problem-solve, bounce ideas, and learn from someone who’s walked a similar path.

Now do it for yours.

Ready to build that rhythm into your first 90 days? I have 3 spots open for a 90-minute 1:1 session. We'll map your milestones, set up your preparation practice, and build a clear accountability structure for what you're building next. Book here: cal.com/olammide

Every sprint, every launch, every quarter, you sat in that room and asked the same questions. What worked? What didn’t? What do we do differently next time? You held every product you ever shipped to that standard.

The moment you started building for yourself, you stopped asking.

I went FOUR months into my first business before I realized I was making the same mistake in month THREE that I had made in month TWO. I just hadn’t stopped long enough to notice. I was moving, pitching, posting, building, and I mistook motion for progress. They are not the same thing.

In corporate, the retro was the mechanism that kept us honest. Not the strategy deck. Not the OKRs. The retro. The moment you sit down and say: here is what we thought was true last month, and here is what we actually found out.

Without it, you don’t learn. You just repeat.

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The question that changed how I run my business isn’t “what worked?” or “what didn’t?” Both matter, but they’re backward-looking. The question that changed everything was the third one:

Most of them haven’t.

I started doing monthly retros on my own business. Not in my head. On paper. Thirty minutes, once a month.

Three questions, written down, answered honestly.

What worked this month?
What didn’t work this month?
What assumption did I have last month that I now know is wrong?

The third answer is where the real work is. It is where you find the thing you have been avoiding. The offer that is not landing. The audience that is not converting. The part of your strategy you have been protecting because you are too attached to it to let it go.

You already know how to do this. You ran retros on products that were not even yours. You were rigorous on behalf of someone else’s quarterly targets.

Write it down. Every month. The pattern you have been missing will be on the page within three months.

You can’t fix what you won’t look at.

If you want to do this with someone who will ask you the third question and not let you off the hook, I have a few spots open for a 90-minute strategy session. cal.com/olammide

The day I left corporate, I packed up fifteen years of marketing strategy and took it with me.

Then I spent the first six months of entrepreneurship writing my own captions, managing my own inbox, chasing my own leads, building my own decks doing everything except the one thing I was actually good at.

At Amazon, I didn’t write code’s for data. I built systems to automate data.
At Nokia, I didn’t chase leads. I built go-to-market frameworks that generated them.
At Jumia, I didn’t manage campaigns. I built the operating model that ran them.

The moment I became a founder, I forgot all of that.

And I stayed exhausted for a long time before I understood why.

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The thing nobody warns you about

Leaving corporate doesn’t transfer your biggest asset automatically. You have to consciously reinstall it.

Most of us don’t.

Because entrepreneurship arrives with a very loud to-do list. Content. Clients. A website. An offer. A price. A brand voice. You need to figure out all the things you used to have a team for and the urgency of all of it is immediate and relentless.

So you get busy. And in the busyness, you become the person who executes instead of the person who builds the system for execution.

You trade the skill that made you exceptional for the urgency of everything that feels like it needs to happen right now.

The exhaustion that follows isn’t a productivity problem.

It’s a positioning problem. You’ve taken one of the most strategically capable versions of yourself and quietly handed her an assistant’s job description.

What it actually looked like for me

At Jumia, I built the operating model that ran marketing campaigns across multiple markets. I didn’t touch the campaigns. I built the architecture that made the campaigns possible.

When I went out on my own, I was running every campaign myself. Manually. From scratch. Every time.

Not because I didn’t know better.

The shift

I stopped asking: what do I need to do today?

I started asking: what is the system that means I never have to answer that question the same way twice?

For me, AI became the team I used to have so I could go back to being the architect.

But the tool was never the point. The shift was deciding that my business deserved the same quality of thinking I had given to other people’s businesses for over a decade.

That decision is available to you right now.

You don’t need a new skill to make it.
You need to stop treating your own work as the thing that gets your leftover thinking.

The real question

You left corporate with more expertise than most people will ever build.

The question was never whether you have what it takes. You answered that in boardrooms and budgets and briefs, for over a decade, for other people.

The question is whether your business is getting the architect.

Or just the doer.

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P.S.I’m building an AI prompt pack specifically for strategists who want to work like architects again not execute like assistants. Reply “stack” and I’ll add you to the early access list.