Why I Left the Company I Gave Everything to, and What It Taught Me about What I Really Want

Earlier this year I left the company I founded and poured 12 years of my life into. I've tried to make sense of why I left, what I learned, and the insight it’s given me to what I want for the future.

Earlier this year I left the company I founded and poured 12 years of my life into. In this post I’m aiming to make sense of why I left, what I learned, and the insight it’s given me into what comes next. Hopefully this is useful for others. The reflection has been useful for me.

I started Sideways 6 as a naïve 24 year old with a lot of help from 3 mentors I was working for full time. There was never any master plan, and I didn’t know where it would go. I don’t think, deep down, that I believed it would go anywhere.I was just excited to try this business stuff for real.

The idea came from experience and insight working at the agency run by the 3 mentors. Companies were asking for ways to listen to ideas from their employees and the available options didn’t seem to meet their needs. I was on a one‑year placement through the New Entrepreneurs Foundation and hungrily looking for an idea to put my energy behind. This one seemed good enough to me.

Months of prototyping, and customer development followed. I reached out to hundreds of potential customers, hastily prepared a first website and built a deck to talk through the idea. Before long I had some amazing people at a well-known company interested in being our first customers. I googled ‘SaaS sales contract’, found something plausible, made a few tweaks, and sent it off. A month or so later, it was signed. We had tens of thousands of pounds in revenue overnight. I remember being ecstatic.

Other pinch‑me milestones followed; hiring our first employee, moving in to our first office, getting our first press, raising investment. It was all so exciting. This little idea was now a very real business with income and outgoings, shareholders, customers, partners and other very real, very dedicated people who had joined the team to make it all happen.

We kept growing. Not without challenges - there were several near‑death moments, years where growth was very slow, and a lot of stress along the way. But we grew. By 2022 we’d reached over 40 employees across 2 permanent offices and millions in annual recurring revenue. We were working with some of the best known companies in the world. Our product was (and is to this day) the best in the market.

What changed

But on my side, the buzz was fading. Most of my time was now spent managing people - more people bring more people problems, and almost every problem in a company is a people problem. I felt removed from the doing and felt I was less able to impact results. I’d hired a leadership team and had listened to the common startup advice that my job was to bring in the right people, give them resource, and get out of their way. I was absolutely not in Founder Mode.

The ups and downs were taking their toll. Without co-founders to turn to and with a misplaced (on a lot of reflection) feeling that crises and big challenges were mine to deal with alone, I felt isolated, lonely and stressed. Successes felt like a reprieve - maybe an opportunity to catch a quick breath, but certainly not to be celebrated. I was on high alert 24/7. Every challenge - a customer threatening to churn, a scary cashflow forecast, a regrettable resignation - felt existential to the company and often to me personally, too.

After nearly a decade working on the project and proud of where we’d got to, it felt like the right time for a new phase, a new inflection point.

In 2023 we were acquired in a deal that I think everyone was and is happy with. The company that bought us is an excellent company. A market leader with a high density of great people. Working with the CEO and leadership team was a real pleasure and I learned a lot from their leadership. Seeing our acquirer’s strengths shone a light on where we’d been making mistakes, and I think my influence on the leadership team was additive to the group, too.

Sideways 6 grew under the parent company’s influence. As always, it wasn’t a straight path and there were many ups and downs, but by my final year at the company was our best ever on almost ever measure - revenue, growth, profitability, etc. It couldn’t really have gone much better. And yet, 27 months after we were acquired and 138 months after starting the company, I left in June 2025.

Why I left

When I close my eyes and think of my highlights of working Sideways 6, most of what I see are the early days. Time spent locked in meeting rooms prototyping, sending photos of wireframes for early product features to my CTO and pushing them live days later, and late nights trying to come up with new ways to find new customers. It’s the creating, the solving, the doing - often with other people just as keen as me, often in response to what felt like existential challenges that somehow felt galvanising rather than scary.

I think of a 2 hour train journey to Sheffield where I built us a new website. I think of giving a demo to an Australian company at 11pm in the bedroom of my shared flat while my girlfriend slept feet away and the elation when they ended up becoming a customer. I think of the Friday ritual in the first few years where we’d go to the pub for a pint at lunchtime and then spend the afternoon booking meetings - by far our most successful hours of the week.

While the company was now in a significantly better place than it was while any of this was happening, my own motivation and engagement had dipped for it’s absence. As a company we were much more mature, much stronger, much more secure and we had much better long-term prospects - but I missed the feelings from those earlier days.

I found myself yearning for scrappier times with higher velocity of output. I bristled at conversations with my team that involved planning quarters ahead, and I longed to be on a maker’s schedule.

I also started to feel a challenge that I didn’t know who I was without Sideways 6. I started to define my whole self as the founder and CEO of the company, and because it permeated into pretty much every second of every day, I didn’t know what I would be if I wasn’t in that role, and that was pretty scary.

As the company had evolved, I’d ushered parts of myself away for the greater good. I’d not been fully, authentically me because I felt like versions of me would lead to better results. This was starting to grate, but I didn’t see a way of bringing my whole self back this late in the game.

Finally, I was struggling with purpose. I’d always felt a strong sense of purpose growing the company. It hadn’t actually come from our mission, though our product is a net positive in the world and birthed some incredible ideas. The purpose i’d felt had always been around answering the question ‘how far can I take this?’. Each new phase - first customers, first revenue milestones, first employees, getting to acquisition - was invigorating. But the feeling had faded.

What this means for the future

It’s now a few months since I moved on, and I’ve got my mojo back. I’ve de-stressed, been fortunate to spend some amazing time with my wife and baby, and there’s been room for much introspection and learning.

I’m beginning to build again, only this time I’m aiming to be more intentional and thoughtful. I’ve set new rules for anything I work on from here on in. I’m aiming to take the best of my previous experience and avoid some of the pitfalls and challenges from last time around.

The new rules:

1. Enjoyable & Interesting; In line with my curiosities. Aligned with my values. Likely to lead to enjoyable days, weeks, and months.

2. Stay free; Able to run a great business while meaning maintaining control of the business and my day-to-day, week-to-week schedule.

3. Compounding; Even if it fails, I learn valuable things and meet valuable people for my next ventures and investments.

4. Fits the life I want to live; Allows for travel, time with family, working out, time in nature, etc.

5. Spend time with interesting people; Learning and connecting with people I admire and respect.

6. I’m a top 5% founder: Some combination of my experience, skills, interests etc gives me an advantage.

7. It’s real and pain-based: A painkiller, not a vitamin. Provable customer demand. Clearly solves a high priority pain for people/companies with money to spend on solving it.

8. AI resilient: Unlikely to be made obsolete or see major challenges by likely progress in AI. It still matters in an AI world

9. AI-first: Able to benefit from being run in an AI-first way using latest and greatest AI tools. Gets better as AI gets better

10. Makes money: At least funds [x] per month personal burn relatively quickly. This can be achieved by hitting [x] per month take‑home within one year, a clear path to [x] a month take‑home within three years, or a clear path to a [x] sale within five years.

11. It matters: I could imagine spending the next 20 years on this project, working hard for long hours when needed and not burning out. It’s not bad for the world (it doesn’t have to be saving the world) and has meaning to me and/or sparks curiosity.

12. Capital: I can get to profitability or major milestone for under [x] + 3 months of my time without external capital.

13. Team: Can be run with a lean team. I won’t need to hire ‘bodies’ to bring the idea to life. Scale doesn’t come from headcount. Potential for a great co-founding team

I’m grateful for everything over the last 12 years and indebted to everyone who helped make them such a success - and now i’m excited for everything yet to come. Onwards and upwards!