Why founding a startup in your 40s beats doing it earlier

If someone says ‘startup founder’ to you, chances are that you’ll immediately think of a 21-year-old kid straight out of college, looking to change the world with a photo-sharing app.

While that stereotype is a stereotype for a reason (there are lots of people who fit that mold), there are plenty of older people who become tech entrepreneurs after long and successful careers in more conventional lines of work.

What made people aged 40+ take such a big change of direction in their lives? And was it worth it? Is not fitting the stereotype an advantage or not? I decided to find out.

Read on; it might convince you to make the jump, too.

John Berthels

Age 47. Based in Nottingham, UK. Co-founder of Cocoon.

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What’s your story? 

I used to be with Trend Micro after the startup I worked for got acquired by them. Like a lot of men in their mid-40s I started to think about the themes of my life and decided I wanted to be an entrepreneur. It’s the same motivation that leads men to drive across the US on a motorbike.

I had ideas for my own startup project but the Cocoon team was forming at the same time and I ended up joining as a cofounder. We’ve taken the project first to crowdfunding and on to our first funding round.

Has your age affected your life as a startup founder?

It’s helped prepare me for not being worried about my capabilities in scaling the company. I know what company I want to build and know what kinds of things I need to consider while doing it. That’s because of the experience I’ve gained through my career as I’ve gradually increased in seniority.

People are relatively open minded about my age. When we meet people, they’re not always sure who’s in charge. The oldest person on the founding team isn’t necessarily the most senior or experienced, as you might expect.

The hard part is walking away from a steady job. I’ve got three kids. It’s only been possible to become an entrepreneur with deep support from my partner.

What would you say to someone thinking of moving from a steady job into entrepreneurship?

Longterm happiness is important. With a strong relationship you can put your collective happiness on the line because you’re in it together. You have permission to fail – you can take that step into the unknown because someone is there to pick you up if you fail, with the understanding that you’ll do the same for them.

Give yourself a window of time to explore your entrepreneurial plans and have a plan B and plan C ready for if you haven’t made enough progress after that time is up.

***

Grant Robinson

Age 40. Based in Wellington, New Zealand. Co-founder of interaction design software startup Atomic.

What’s your story? 

I’m a design practitioner by trade, focusing on UI and UX and I’d got to a point where I had a say over product direction. I worked for design agencies, and accounting software firm Xero. I enjoyed the startup experience there and wanted to take it to next level.

I had a startup idea with a friend for a ‘Google Docs for design and prototyping.’ I was working at a bank doing consultancy using Adobe Fireworks at the time and Adobe announced they wouldn’t be updating it anymore. We thought about what the ultimate tool could be, thrashed around ideas and decided it was too big to build, but about a year later we decided to give it a shot.

We started with three people last year and have now expanded to 12 people. We launched in open beta in May 2015 and our full launch was in September 2015.

Has your age affected your life as a startup founder?

At 21, I didn’t have an entrepreneurial bone in my body. That’s something that developed over time as I gained experience of my craft. Now I have emotional maturity and life experience. That helps with who to hire, what I want the culture of the company to be. I hate to think what 21-year-old me would have done in these situations, it would have been a trainwreck.

We’re based in New Zealand, and investors here are more risk-averse than in Silicon Valley. There’s an emphasis on experience and track record, so my age is an advantage.

We have families, so can’t do crazy all-nighters like some younger founders do, but we haven’t heard anyone raise concerns.

What would you say to someone thinking of moving from a steady job into entrepreneurship?

Being a founder forces you to engage with the businesses challenges and goals at a much deeper and holistic level, and without the boundaries on the ways you’re able to make an impact that you’ve probably become used to being an employee within a larger organisation.

Put simply, it’s the fastest way to learn and grow as a professional. I wish I had done it sooner, and after you make the jump you almost certainly will too.

***

Dean Elwood

Age 44. Based in London, UK. Co-founder of VoIP tech startup Voxygen.

What’s your story? 

I’ve got a risk-averse profile. I was interested in maths and computer science as a child but family pressures led me into a career as a lawyer. I wanted to combine law with my interest in technology by working on patents but I wasn’t good enough so got stuck for 15 years working on mortgages and the like.

In my late 30s I decided I was unhappy. I was earning reasonably good money and was comfortable but I had to get out of my law career. After I did it I wished I’d done it years ago.

I had started playing around with telecoms technology in 2001 when I built a phone network in my flat. I started a website called VoIP User that offered one of the earliest VoIP services and got invited in conferences and events to speak about it. That led me to join VoIP startup Truphone in 2007 as Platform Director.

I started Voxygen the following year. We worked with Skype before it was acquired by Microsoft, and more recently have worked with O2 on products for their customers.

Has your age affected your life as a startup founder?

It’s difficult to be a founder in your late thirties; it’s hard to raise money. It was hard in the UK a few years ago anyway, if you weren’t 21 years old with a rockstar coding cofounder. I had to just go it alone, funding the company with consultancy work.

While 21-year-olds have more energy, your priorities change as you get older. You’re more ambitious to be financially successful when you’re 21 but money is less important in your 40s, so I can see why investors focus on younger founders. But while I’m less ‘hungry’ than when when I was younger, I’m better able to get to my goal than I would have been then.

My previous experience is useful as a founder. I use my law background every day. In the early days it helped as I meant I could draw up contracts myself, which was a massive advantage to a young company.

As a young lawyer in my father’s boutique law firm, I worked with very rich clients and I saw how they negotiated. I’m also better able to get on with people, and more life experience means I can better see the ‘bigger picture.’

What would you say to someone thinking of moving from a steady job into entrepreneurship?

Do it. Whether you succeed or fail it’ll be the best thing you ever did. Even if you fail, you’ll have great experience to take to whatever you do next.

***

Elizabeth Shassere

Based in Sheffield, UK. Founder of healthcare-focused SMS service Textocracy

What’s your story? 

I had a career in public health in England and about eight years ago I became a Director of Public Health. I got to know local government and local primary care trusts (as they were at the time) very well, and they are not at all conducive to innovation and creativity and problem-solving. There’s a ton of bureaucracy, a lot of fear around decision-making – no risk allowed whatsoever.

I’m an ideas person, I like to solve problems and make things better so it became too frustrating and not a place I wanted to be anymore.

I knew I wanted to start my own business and become an entrepreneur but I didn’t know what that meant – I didn’t have a frame of reference, it just sounded exciting. I moved to Sheffield and someone at an entrepreneurs festival said I should go to a Startup Weekend that was happening in November. And I thought ‘why would I do that? I don’t know anything about tech, I don’t even know what a startup is.’ And they said ‘you’ll meet people, it’ll be fun, you’ll learn stuff.’

So I turned up on the Friday night and was encouraged to pitch, but I didn’t have a startup idea. So I sat in the audience listening to other people’s pitches and I thought I’d have to blag my way onto a team because I had no tech skills and I was a lot older than the other people in the room. I thought I was going to be the kid who doesn’t get picked for the team.

An idea for an SMS-based healthcare appointment management system for GP practices popped into my head and I thought ‘what the heck, I’ll give it a go, nobody knows me.’ So I pitched this idea and I ended up winning the weekend with the idea.

Someone said ‘that’s just beginner’s luck, I bet you can’t do it again.’ And there was a Lean Startup weekend happening in Manchester. I arrived with a half-baked idea and on the opening Friday night I couldn’t get a team together but I took that idea through myself and ended up winning that one as well.

As part of my prize, I had an MVP built for me over three days. It’s that MVP that I’ve built the business with and got me the traction to get 12 customers, with more in the pipeline. I’ve been engaging with councils and NHS (National Health Service) services and HealthWatch chapters for when it’s ready to scale up and crack those markets open.

The people at the Lean Startup weekend run by FutureEverything and at the Dotforge accelerator have been so supportive. No-one said I couldn’t do it, even just as a ‘team of one.’ Nobody took a look at me and said ‘who are you to be doing this? You don’t know anything, you’ll never make it.’

I applied for accelerators and I was a little cocky. I didn’t realize how little I knew. Dotforge was kind to me in telling me nicely that perhaps I wasn’t ready for an accelerator. So over the course of the last summer I was able to tweak the design of the product and start selling it and applied for the Manchester cohort in late 2015.

Has your age affected your life as a startup founder?

The public sector is really rife with really naughty, wicked problems – tough issues. They’re not easy to solve at all and you have to be really diligent, resilient and creative to chip away at these problems. You often have to circumvent barriers that are put up by the organizations themselves, around their history and culture. That kind of creative thinking, problem-solving and resilience has been really what’s got me here today because it would have been so easy to give up on so many occasions.

The other thing is because I worked at executive director level, I had to work with big teams and big budgets. Knowing that I had to have a strategy and vision to have those people come along with me on a journey has made it possible for me to have a vision for Textocracy, something that I feel passionately about. I’m a more or less a ‘team of one’ right now. I’ve got a great advisory board and people who are helping me out, but now I can build a team to take it to the next level. So the strategy, leadership, the vision – that’s really important in a startup, I’ve found.

No-one has challenged me personally, and no-one has been horrible about it. Everyone’s been very welcoming, supportive and friendly. There is something inherent in the culture that isn’t at all I think intentional or malicious, but it does create an atmosphere where sometimes it’s difficult to fit in or get things done.

One of the oddest things i’ve found is that because I’m older and have had a leadership role and worked for many years, people assume I don’t need any help, so they don’t tend to take my pleas for assistance very seriously. It’s not that they don’t want to help, they just aren’t sure how to help and I don’t think that honestly I could use as much help as the person next to me who has maybe no work experience and is just starting out. I’m just starting out too, and there are plenty of things I don’t know.

What would you say to someone thinking of moving from a steady job into entrepreneurship?

You’ve just got to do it. Put any fear or doubt aside. You’ve got to acknowledge that your skill and experience is very valuable and that you have something that nobody else might have in a startup scene.

The real-world experience that I bring, the knowledge of problems and barriers to those problems – I have a list a mile long of solutions I want to build and so now I’ve got my own startup and I’m meeting people who want to help me build solutions to problems – there’s nothing stopping us because I’ve got the information and they’ve got the skill and together we can solve all kinds of problems.

Just get out there and do it. People want to help. I’ve not met anyone who didn’t in some way want to help and support me. Especially for older women, just go for it. Put your fear aside and do a startup weekend or a hackathon or any opportunity you might have in your community. When you put ideas with skills and experience there’s just nothing stopping you.

***

Scott Nelson

Age 46. Based in San Francisco. Founder of BigControls.

What’s your story? 

I’ve really been in the same industry my entire career. I started out on the government side for five years and then switched gears and went into the (at the time) ‘big six’ public accounting field. So I’ve always been involved in the area of corporate tax credits and incentives and I used to run practices on the West Coast – one for KPMG and one for Ernst & Young – and eventually started my own firm in 2003 and another later in the professional services area.

I eventually wanted to marry my expertise with technology in Silicon Valley and came up with an idea and took the plunge to step out of my existing roles.

Has your age affected your life as a startup founder?

I’m learning a ton. I’m still in the same general industry but now I’m productizing my knowledge from over the past 20 years. After a long time building up contacts in the established financial institutions and investment banking, I now have to get close to the VC world and I’m finding myself at a little bit of a deficit in terms of my network.

Thankfully, I have a fantastic team of advisors. I learned that was important early in my career – get the right people in place early.

There’s an unspoken stigma of being over a certain age as a startup founder but my background and experience has been fantastic in this space. I’ve been able to leverage the ability to execute – I understand what execution is, I learned that early in my career and focus on it here.

What would you say to someone thinking of moving from a steady job into entrepreneurship?

You have to be comfortable with risk. The potential for failure is always in your mind but for me it’s so far back that I just don’t even think about it. For me, there is no failure. You’re either cut from that cloth or you’re not.

There’s a lot to be said for wanting to build something that’s yours and solve a problem in the world – passion and obsession that means you’re not afraid to take a risk.

***

Steven Rahseparian

Age 43. Based in San Diego. Founder of Secured Universe.

What’s your story? 

My first computer was an Atari 400 when I was nine years old and not many people knew what computers were. By age 12 I’d sold my first computer package and when I was 17 I had my own computer store. When I went to school at Penn State I started one of the first ISP services with a professor there and my current co-founder.

From there I got recruited to a company called Winstar Communications, which was a big company – a Wall Street darling – that was a competitive local exchange carrier with wireless for the last mile. That was the beginning of my corporate career. After that I had my own consulting firm for 15 years with a stable customer base and reliable income.

Then I realized there was an area around mobile security for Android that I really wanted to focus on. So I shut everything down to focus on it. That was a big step because I’ve got two kids and a mortgage. I had no comfortable nest-egg that would make it okay for me to fail.

Some people look at me and say ‘you’re crazy, why would you put yourself at risk?’ But the reason is that it’s bigger than I am – what I want to do is not just about building a business and having money, I want to leave my mark. One day I can my own Wikipedia page and people will say ‘he’s the guy who solved malware,’ or ‘he’s the guy who made us a little bit safer’ – some kind of legacy for my kids.

Has your age affected your life as a startup founder?

It’s a much bigger risk now than if I was in my 20s. I’m not couch-surfing and I can’t go back to live with my parents if I fail. You have no choice – you have to make it.

There is an arrogance amongst certain angel investors and VCs. They judge me on my age, but that dissipates when I talk to them about how security suffers because of the lack of experience in tech companies – people think about security last. None of my team is in their 20s because it takes a lifetime of experience and understanding how we got here to solve this problem.

This isn’t a simple app that does something silly and solves an easy problem. This is something that a 20-year-old out of Stanford is not going to be able to comprehend or attack as effectively because they don’t have the raw experience of decades of having to deal with software vulnerabilities.

What would you say to someone thinking of moving from a steady job into entrepreneurship?

There are two types of people in this world and you need to be real sure which one you are. You might be better working for someone. If you’re an entrepreneur you’ve got to be willing to sacrifice everything – your comfort, your security. You’ve got to be prepared to sell your wife’s engagement ring to make one more month of payroll if you need to.

You have to be all in, with your family along with you. You have to be able to start from scratch and keep rebuilding if you don’t make it the first or second time. If you can do that then go for it.

Some contributing founders for this article were found with the help of the Input feature by Index.co, a TNW sister company.