Beware! This is how startup life REALLY looks.

by | Sep 2022 | Start a Company

Kayode Odeleye is 41 next month. For over 15 years he was a banker, working in leveraged finance. He neither loved it nor hated it, but he enjoyed the standard of living that investment banking afforded his family.

In 2020 he resigned.

Kayode Odeleye, founder of Caena
Kayode Odeleye, founder of Caena

As Kayode approached 40, he began to feel there must be more to life. If he didn’t follow his dreams soon, perhaps he never would. That was 18 months ago.

Today, Kayode runs his own 6-person startup. The company is building Caena – a software platform that eases the friction between investors and founders. Fantastic.

Or is it?

You see, it’s not what Kayode’s building that took my breath away; it’s how he’s building it.

Since 2020, Kayode has invested over $100,000 of savings to build his business. And for 18 months he hasn’t received a single salary payment.

When he explained, I wanted to give him a hug. Kayode is exactly the reason my partners and I started DQventures.

Gung-ho propaganda

What is it really like to be a startup founder?

There is FAR too much irresponsible talk in startup land…

“Just do it.”

“If you don’t try, you’ll never know!

“Move fast and break things.”


But what if that “thing” you break is you?

Founding a successful startup is almost impossible. Sure, if you’re 20, you have very little to lose, so why not try?!

But if you’re 39, like Kayode was, “just going for it” is a MASSIVE risk.

Think you’re better than most? Of course… we all do. Most don’t make it.

In my view, for people who are mid-career, launching a startup is madness.

You’re putting all your eggs in one basket – career, income, savings, family, reputation, self-esteem, mental health. You may not see it that way yet, but it’s all there. Genuinely scary.

We founded DQventures for people exactly like Kayode.

“Don’t Quit!”

(See what we did there?!)

All three of us – myself, Oliver, and Arjun – believe that experienced professionals should avoid, at ALL costs, leaping into a startup, feet first.

There are a million things you don’t know or understand. Make one mistake and it could cost your life savings… and much more besides.

You may discover, as Kayode has done, just how incredibly difficult it is to build a software company from scratch.

Assumptions that proved incorrect

Kayode told me that many of the assumptions he had made proved entirely false. These surprised him, as he’d never considered them. Kayode’s belief is that these things aren’t well known because few people talk about them:

Here are some lessons I learned the hard way:

– Your existing network is a bubble and will be completely useless to you when you go into tech.

– 99% of your close friends won’t invest in you or support you in any way. Help will come, but from where you least expect it.

– 23-year old VC analysts will scoff at your ideas and will proceed to lecture you. You’ve got to listen to some of what they say (ditch the corporate speak and DCF slides) and ignore the rest.

– Your experience is immensely valuable but tech skews to favour the young. You will be treated as a relic.

– Building a tech startup is hard. Don’t believe in the hype. Only embark on this journey if you’re ready for pain. Intense, debilating pain. Chances are your startup will go to ZERO. The stars have to align for you to succeed. Work hard, curry luck and stay humble.

– Finding support specifically geared to the “old” & experienced is rare.

Fantastic advice from someone who’s been there and done it.

As a startup founder, how can you mitigate risk?

There are two things that can help make the startup journey less risky:

  1. You have a working spouse, whose salary will pay the bills; or
  2. You have a trust fund. (You wish!)

If you don’t have one of the above, whatever you do, please don’t throw caution to the wind. Find a way to bootstrap your startup without giving up your income. Find a partner like DQ (hit us up any time), run the business as a side hustle… maybe pay someone to run it for you.

Just. Don’t. Quit.

Trust me, at your stage of life, if you go all-in, you CANNOT afford a failure.

If you don’t believe me, ask Kayode.


Image credits

– Piranhas by Reimund Bertrams.
– Kayode Odeleye, courtesy of Kayode himself.
– Cliff image by Ashley Jurius.
– Startup image by Gerd Altmann.
– At the edge of the abyss by Alexa.

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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