How I Did It - What To Know When You Leave A Corporate To Found A Tech Startup

8 Min Read

We interviewed 7 of London’s entrepreneurs across a wide range of industries to find out the first steps they took to leave a corporate career and build a startup. The full interviews are all indexed right here, but in this blog, I’ve distilled the best bits, the absolute key takeaways any founder needs to know for when their startup is at its most raw and vulnerable - the beginning.

You find a lot of guff around startups, this isn’t guff, this is proper tangible advice from founders, guff can fuguff off.

This blog’s broken down into

  1. Why someone leaves a corporate career in the first place
  2. The challenges of building a tech product
  3. The challenges of doing the right thing

Why Does Someone Leave A Corporate Career?

Starting a business is usually the worst move you’ll ever make. On a statistical level, it’s scarcely a better financial decision than just trying really hard at winning the lottery. On a mental level, it’s even worse than that.

Our entrepreneurs shared their mindsets and motivations for making this unwise decision, and if they don’t resonate with you, and you’re still chasing those dollar signs, then may I remind you lottery tickets costs £2 a pop and Vegas return flights can be as little as £300.

I Was Bored Everywhere

For Electra Japonas, founder of The Law Boutique (read her full story here), her corporate career at the likes of the European Space Agency, Disney, and EY simply made her bored: “I’d always worked in huge corporations and I was bored everywhere - I couldn’t stay longer than 18 months, couldn’t progress quickly enough, nothing was creative enough, red tape everywhere.”

Richie Barter of AltViz (full story) was also getting bored and when he looked up the career ladder he was seeing that boredom, not personal fulfilment: “In my day to day job I was spending more time in middle management strategy meetings than doing anything interesting. It was really stifling to me in my early thirties. You ask yourself, do I want my boss’s job? What’s the 5 year goal here? I didn’t see anyone there that I wanted to end up becoming and in your early thirties you should have a sense of it.” 6 years later, he has a VC-backed machine learning startup AltViz.

For Lu Li (Blooming Founders) and Kim Guest (Isoshealth), boredom was not the issue, it was the sense of restriction. Lu says “my previous role was in a negative space. I didn’t want to deal with people with a closed mindset at all.” Kim adds: “a corporate role is so limiting because it’s this little square box and I’d go into a room and shake people’s hands and say “Hi I’m Kim Guest, I’m Commercial Director for Telefonica” and you’re so defined by one job title. Now I can bring all of myself”.

It’s that frustration with purpose and challenge and restriction which drove our entrepreneurs to quit stable and prosperous careers.


But frustration’s a negative driver. It’s enough to make someone quit a job, but is it enough to drive a startup? The positive driver is usually called passion.

Joe Scarboro, founder of the Bot Platform and Touchpaper, had this to say about passion: “For corporate leavers looking to start their own business, you must start doing something which tests how much you like your idea before you quit your current role. It’s important to avoid the hyperbole of entrepreneurship… Quite simply, if you’re not purpose-driven and in it for the long-haul, you won’t get very far.”

But, the problem with entrepreneurship is that the better the job you do, the sooner you stop being… an entrepreneur. As in, within a couple of years your business will look like the corporate you left, there’ll be employees and processes and red tape.

Richie Barter again: “I agree you need to know that you’re passionate enough in the idea before you start putting in all your effort, but your role evolves. Any entrepreneur has to have multiple hats and as the team grows or retracts you give those hats away and you have to evolve your passion along with them. Yes you need passion, but it becomes more nuanced.”

The Challenges Of Building A Tech Product

If you’re founding a company with a tech product integral to its success, and you’re not technical, then you will need to skill up fast and recruit a top whack CTO.

6 out of 7 of our entrepreneurs did not have a programming background. Only Tor Gisvold (Adarga) was a career technologist, building technology products over decades at the likes of News International, Riot Games (League Of Legends) and PwC. His words on the hiring a CTO thing you’ll need to do, and building the team to go with them, are gold dust because he’s been there and done that, he’s who you would want to hire.

Here’s the mindset you need: “Get someone who’s hands-on. The CTO has to be able to code as well, not necessarily to production standard but they have to walk the walk.”

Richie Barter said that he’d learnt through hard experience that “process is everything. You want to know what process are they going to bring, what’s their delivery, their deployment process, their hiring process, their learning development process, the good measurable confident processes.” All great questions to ask a potential CTO.

Tor Gisvold pointed out the non-technical responsibilities of a CTO: “a CTO role in a startup is extremely multifaceted, you’ll spend as much time on sales and business development and pricing strategies as on hiring and technology architecture. The CTO needs to do all those things while being able to spin all the plates and take the pressure.”

And how do you fight off PwC for a CTO like him?

“You don’t get someone like me with money. There has to be a moral behind it, my best project was fighting Ebola for WHO. There is a buzz from doing it and it is its own reward, and everyone wants to do it one more time… My founder and I met when I was working on the Panama Papers. He had forty people reading the papers and I said to myself there must be better ways of doing this.”

And then, how do you become technical, enough to start the business and attract the money to re-invest in hiring proper devs full time?

What surprised me was just how different the route each founder had taken to becoming technical. Take a look at the below, there’s a route for everyone:

  • Code camp on maternity leave - Sara Tateno (Happity) is the sort of multitasker who views pregnancy as a great way to take a generous redundancy from the BBC, start a mini-accelerator with the baby at ten days old and then, when it’s hubby’s turn to take parental leave, undergo an intensive 12 week coding course.

    Here’s her reasoning: “I felt too far removed and inexperienced from the tech startup world and not well geared up to work with and communicate with developers. Not just that, but so many opportunities are now in the tech sector. I wanted to upskill and ensure I’d be well placed to start anything I wanted in future.”

    Her startup Happity is now a year old and doing really well.

  • Fake It - Electra Japonas uses nine platforms integrated into a Squarespace website, platforms such as Typeform, Mailchimp etc. Squarespace, Wix, Wordpress, all great ways to get a template up and working which you then customise with these platforms. Most people at the beginning do not need complicated bespoke solutions, and cobbling together this mishmash is the fastest, cheapest and least stressful way to do it.

    Electra said “I thought well I’m not going to spend loads of money on my own website to start with, so I built my own in Squarespace. It was time consuming but valuable because until you write out what the world’s going to see of your startup, you don’t truly know how you’re going to position your product.”

    Sara Tateno would agree: “There are many tools you can use to create a proxy for your MVP without much cash or development. It’s easier than ever to prove a concept and secure your first customers without building anything.”

  • A Degree From Oxford - Richie Barter went one step further than Sara and obtained an MSc from Oxford “which is part time, they target more junior devs who want to jump up the ladder, or non-techs like me who can prove a technical aptitude. You can do a couple of modules and be graded and see how you get on, it helps you understand if you can keep up with the material. That MSc was a foundation for me in terms of cloud computing, designing scalable data systems, algorithm selection etc”. It was his way of studying part time, with a way to cut it short if it was the wrong decision, or at least have a qualification to show for all the startup effort. You don’t HAVE to go with Oxford though… the principle of intensively studying code is the main takeaway here.

  • Accelerator - accelerators come in all shapes and sizes, Kim Guest chose hers, Activate Capital, because they could give her a coding functionality, give her a team and actually an interim CTO. It was like outsourcing the development, but still having complete control and alignment of purpose: “My team deeply immerses themselves in the challenges. It’s not just what your platform will look like, it’s what’s your mission!”

Her advice for those outsourcing production was “when looking to hire a team, look at the collaboration between design and dev in the team, ask where do those two sit together, what tools do they use. If they only use github and never talk to each other that won’t work. My team is international, in Rio, in Delhi, in London, but practical stuff was never an issue because they communicated.”

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The Challenge Of Doing The Right Thing

The problem with pioneering into the dark side of the map is that you don’t know if there’s monsters up ahead. Perhaps that siren call from an investor is not what it first appears, or that little hill you decided to climb has turned into a sand dune slipping away beneath your impotent feet.

Founders are racked by these uncertainties. They can be operating in a new field with little resource and little data, and the question “am I doing the right thing” is what oozes into their brain when the bedtime lights go off.

I don’t think founders hear enough about that uncertainty. We’re used to Elon Musk bravado, hockey stick graphs, “smashing targets” “raising millions”. Bullishness is a great asset to ambition, but it’s also dangerously close to bullshit.

If there’s anything to take away from this blog, it is that you can read up on all the practical tips you like, research all the plans and contingencies, build the kind of detailed roadmap your boss at the corporate would adore.

They mean nothing if you can’t handle the uncertainty.

The Number Of Things You Don’t Know Is Astonishing

Lu Li, founder of London’s biggest network of female founders, struggled with making the spending decisions, what to spend on what: “there were several times where I spent money on things that didn’t bring any ROI and which hurt quite a bit. Also, the number of things you don’t know about or have a wrong gut feeling on is astounding!”

Electra sums it up: “You get quite lonely starting a business. I didn’t think that would happen. You don’t know whether you’re doing well so it’s very easy to be harsh on yourself. On a deep philosophical level uncertainty is something that holds people back. A startup will force you to understand that you can’t control everything, it will force you to believe everything will be ok, and that in itself is worth doing. It frees you.”

Richie - “Let me tell you, there were very few nights I lost sleep over my old corporate day job where I managed hundreds of millions of dollars. Since I started my own company, the number of times I wake up at 4am because of a certain issue… the years 3-4-5 really impact you in all sorts of ways.”

Joe Scarboro finishes with his note of caution: “being the master of your own destiny is great, but also brings mental baggage”.

What About You?

Now you’ve read all this, how would your passions and frustrations weigh up against the startup challenges on the Scales of Life Choices? Does your resolve to work on your own dreams outweigh the troubles those dreams might bring?

If you need to tip the scales, remember, there are now seven businesses which only exist because of these people you’ve read about today.

Parents book activities for their children with Happity to create the good memories, startups access legal advice with clarity and affordability to grow in security with The Law Boutique, men and women are taking control of their health with trusted practitioners with Isoshealth, insurance premiums can lower now AltViz’s machine learning can reduce loss caused by poor QA, thousands of female entrepreneurs are finding community and strength with Blooming Founders, corporates and startups are working well together thanks to Touchpaper, and Adarga is leading the advances in AI and Machine Learning.

Best of luck guys, rooting for your future successes.

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We’ve interviewed more of London’s fantastic entrepreneurs who left a corporate career to found high growth businesses. Visit our blog to see other stories from ex-bankers, consultants, accountants and more.

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