The Lessons from Building 5 Companies and Investing in 60 Startups
What I believe now that I didn't believe in 2016.
I started a marketing agency at 23 with £50 in my bank account.
Grew it to £2M in revenue with 20 people. Built ContentCal as an internal tool to solve our own problems, then made a decision that confused almost everyone around me: I killed the agency to go all-in on the software.
We raised $14M. Scaled to 4,000 customers globally. Nearly ran out of cash twice. Both times, we were down to 30 days of runway. Both times, we survived.
Then something unexpected happened. I lost myself.
Not immediately. The acquisition looked perfect from the outside. I was there to complete the integration, and I completed it in a fraction of the time they thought it would take. But by year two, the reality had shifted. I was just another product person in corporate meetings that didn’t motivate me. More talking. Less doing. Adobe treated me well, but I had optimised for an outcome that left me trapped mentally and intellectually.
What followed was a deep identity crisis. Personal challenges compounded it. I had to rebuild from scratch. Not as “Alex the founder,” but as a person with a life outside work. Boxing. Cooking. Drums. Friends. Family. The things I had neglected for years while grinding.
I’m now CEO of JAAQ, a mental health and behavioural health company where I was initially an investor and advisor before the board asked me to join as CEO, and I decided to go for it. We raised a meaningful amount last year and are making amazing progress toward our mission.
I’ve invested in 60+ startups. My investments are tracking around 18x returns. Two of those companies are now unicorns. I’ve co-founded a commerce media network operating across 180 countries.
I’m sharing this to explain where the following beliefs come from. Because what I believe now is fundamentally different from what I believed when I started. And these shifts didn’t come from reading books or attending conferences. They came from building, failing, rebuilding, and watching patterns emerge across dozens of companies.
Here’s what I know now.
Speed without direction is expensive, not efficient.
At ContentCal, we started by targeting enterprise customers. Big contracts. Serious logos. The kind of traction that impresses investors.
It was the wrong direction.
We burned a year chasing deals that didn’t fit our product or our operational capacity whilst simultaneously pivoting toward SMB. When we finally committed fully to small and medium-sized businesses, we found product-market fit almost immediately. But only after nearly dying in the process.
This wasn’t a speed problem. It was a direction problem.
The most expensive mistakes I have made in my career weren’t from moving too slowly. They were from moving quickly in the wrong direction. Speed feels productive. It looks like momentum. But direction is what compounds.
In a world that celebrates pace, the ability to choose the right direction before accelerating is increasingly rare. And increasingly valuable.
Calm is a performance edge, not a personality trait.
From 2016 to 2021, I worked constantly.
Weekends. Evenings. Holidays. It didn’t matter. I genuinely believed that the answer to every problem was more effort. More hours. More output.
I was completely wrong.
Post-Adobe, I hit a wall. Not burnout in the conventional sense, but something deeper. An identity crisis compounded by personal challenges and the realisation that I had built a life I couldn’t escape from. I had sold the business, made the money, and then found myself in corporate meetings that didn’t motivate me.
What pulled me out wasn’t working harder. It was redesigning how I work entirely.
Now I work in sprints. Thirty minutes to three hours of deep, focused work on something that matters. Then I stop. I walk. I think. I have a coffee. I go to the gym. I box. I cook. I play drums. I spend time with people I care about.
Calm, as I understand it now, is not about being naturally relaxed or having a mellow disposition. It is about low reactivity when everything is on fire. It is about preserving decision quality under pressure.
The best decisions I have made came when I was settled, not when I was in panic mode trying to save the business. I am more productive now than I was when I worked all the time, because I am not reactive to every message, every meeting, every question. I decide what actually matters and don’t pay attention to the things that don’t matter anymore.
This is not a wellness argument. It is an economic one.
Clarity is becoming the most valuable competitive edge.
When I started building software, competitive advantage came from execution speed and technical depth. You needed to move fast, ship product, and out-execute the competition.
That game is changing. The founders who are winning now aren’t necessarily the most technical or the fastest. They are the ones who think most cleanly. Who can frame problems well. Who ask the right questions.
Clarity is the new competitive edge in a world where intelligence is cheap and information is abundant.
This applies to how you think, how you communicate, and how you decide. The ability to cut through noise and see what actually matters is becoming more valuable than raw intelligence or sheer effort.
Wealth is control over decisions, time, and income.
After the Adobe acquisition, I had more money than I had ever imagined.
But wealth is not the number in your bank account. It is autonomy over your time, your energy, and your decisions.
I was there to complete the integration, and I completed it in a fraction of the time they thought it would take. Adobe was very good to me. But the experience taught me something fundamental about what actually matters.
You can be rich and completely trapped. You can be relatively lean and extraordinarily free.
I will never allow myself to lose control over my career again under any circumstances.
Burnout is a systems failure, not a personal flaw.
I nearly destroyed myself building ContentCal.
Not because I lacked resilience. Not because I couldn’t handle pressure. I can handle a lot. The problem was that I had designed a system that required constant heroics to function.
If your business needs you working 80-hour weeks just to survive, the problem is not you. It is your system. Burnout is not a character flaw. It is a diagnostic. It tells you exactly where leverage is missing.
After Adobe, I became an investor and advisor to JAAQ. Not because I had some grand plan to enter healthcare. Because I had lived through what happens when you ignore every signal your body and mind are sending you.
During my own struggles, I found that good content, podcasts, videos, articles, helped me understand what I was going through. But finding that content was nearly impossible. It was scattered, unvalidated, inconsistent.
JAAQ centralises clinically validated mental health and behavioural health content in one place, then uses AI technology and structured pathways to help people find the right next step in their journey. Content is not well understood or well used in healthcare. It is not seen as a medical intervention when it absolutely should be.
When healthtech combines clinical validation and safety-first thinking with SaaS-level product quality and customer success, it works extraordinarily well. The board asked me to join as CEO, and I decided to go for it. We raised a meaningful amount last year and are making amazing progress toward our mission.
I didn’t step into this role because I had everything figured out. I stepped in because I didn’t.
The best founders are the least reactive people in the room.
I have now invested in more than 60 startups. Two of them are unicorns. I have seen hundreds of pitches, worked with dozens of founding teams, and watched patterns emerge.
The loudest founders often get the most attention. The most reactive ones feel like they are moving the fastest. But the ones who quietly outperform are not the ones responding to every fire, every piece of feedback, every market shift.
They are the ones who decide which fires to let burn out, which ones to put out, and which ones to pour gasoline on for growth.
Low reactivity is not passivity. It is not slowness or indecision. It is decision hygiene. It is the ability to hold pressure without transmitting it. To distinguish signal from noise. To know what actually matters and what can be safely ignored.
When I was grinding at ContentCal, I was reactive to everything. Every notification. Every customer issue. Every investor question. It felt like responsiveness. It felt like good leadership.
It wasn’t. It was chaos dressed up as diligence.
Now I work in focused sprints and ignore most things. The businesses I am involved in run better because of it, not in spite of it.
Leverage is designed, not earned through effort.
At 23, I genuinely believed that leverage came from outworking everyone around me.
I started my own marketing agency with £50 and grew it to £2M in revenue with 20 people. Then I made a decision that confused most people: I killed it to go all-in on ContentCal.
Why? Because I wanted to get rich and learn as much as possible in the decade between 20 and 30. If it didn’t work out and I didn’t get rich, at least I would be extraordinarily knowledgeable. That felt like a reasonable trade.
That logic was half right.
Effort got me to £2M in agency revenue. But it was completely linear. More clients meant more revenue. More revenue meant more work. There was no compounding. Just grinding.
Leverage got me to building an amazing software business where revenue compounded and we solved a massive problem, which led to a category-defining exit in social media marketing technology.
Now my startup investments are tracking around 18x returns. Not because I work harder than other investors. Because I make good bets on the right founders in the right industries.
Effort is honest. I respect it deeply. But it scales linearly.
Leverage compounds exponentially. And leverage is not something you earn by working longer hours. It is something you design by thinking more clearly about what actually creates value.
Welcome to Venture Wisely in 2026.
This platform exists for founders, operators, and investors who have realised that the loudest path rarely leads anywhere worth going. It is for people optimising for clarity over speed, leverage over effort, and building things that compound quietly over years instead of burning bright for months.
I don’t write to motivate. I write to help you think more clearly about what you are actually building, and whether it is worth the cost.
If that sounds like the game you are playing, you are in the right place.