How it feels to lose $2m of other people’s money.

by | Oct 2022 | Updates

This is a painful true story: I lost $2m of other people’s money on my first startup.

It’s surreal to write it, but it happened. (All you founders out there raising money, be careful what you wish for. I didn’t think it would happen to me, either.)

The embarrassment of failing was nothing compared to the guilt of losing my friends’ and family’s money.

After 6 months feeling lost and doing some consulting, I needed a job. We’d had our first child and we needed an income. Despite saying I would never work for anyone else again, it was time to write my resume.

Nobody wants to hire failed founders.

I couldn’t get a response.

3 months of searching later, with only one telephone interview to my name, I felt desperate.

It turns out that it’s hard for founders to get back into employment after failing in startups. Startup founders are generalists, but most companies need specialists. If you’re a good founder, you’re a great match for one job – starting another business…

…but that’s probably not a job you particularly feel like doing.

Time to rebuild a broken founder.

Then a friend, another founder, offered me a job.

Time to rebuild.

The role I was offered paid me ~35% of what my peers were earning, but it was a lifeline. I put my head down.

After another year, I started to get my mojo back.

It literally took me 18 months just to start feeling like myself again.

But in that time I realised something.

I was ok at the job I was doing (I think!), but I was really good at helping my friend avoid mistakes… especially the ones I’d made.

Also, as well as adding a lot of value that wasn’t in my job description, I loved it.

I started seeking out other people I could help: founders, capital raisers… even investors.

During that time, I also met my now business partners, Arjun and Oliver. We talked, casually at first, but then with more energy and excitement. We actually had a pretty good idea.

Everything slotted into place.

A new startup idea was born.

A new idea.

Independently, Arjun, Ol, and I had been telling our peers – mostly experienced professionals – NOT to launch a startup (I knew from experience, it was way too risky); but it hadn’t escaped us that these were exactly the type of people we should be encouraging:

  • Bright
  • Deep sector knowledge
  • Strong networks
  • Exceptional EQ

The seed for DQventures was planted. Instead of telling experienced professionals NOT to do a startup, we began drawing on our successes and failures to HELP them launch, while doing everything we could to minimise their risk.

“Don’t quit” became “don’t quit yet”.

Where are we now?

So far we’ve helped 8 founders to get a venture off the ground, with us as co-founders. One is already turning over millions of dollars in revenue and profitable. Another just raised nearly $1m.

We’ve also helped countless others avoid some pretty significant mistakes.

People talk a lot about purpose. This has been a hard journey, but I can genuinely say that I’ve found mine. I literally don’t feel like I work any more. I do what I love (and what I’m best at), and I work with people I like.

I used to say I wanted to retire at 46. Now I don’t want to retire at all.

I hope you can find the same.


If you know someone great, who would dearly love to launch their own company, we would love to meet them. They can connect with any of us on LinkedIn.


Image credits

– Dock image by David Mark.
– Broken Lego man by Jackson Simmer.
– Lightbulb man by Colin Behrens.

Kickstart your business without quitting your day job

DQventures is the only venture investor worldwide to support aspiring founders who cannot afford to give up full-time employment.

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