I'm Going All-In On Joining an AI Fintech Startup

& 5 Questions That Got Me Here

Dec 06, 2024

From January, it looks like I’ll be joining an early-stage startup, numra (website designed by me! 😉), to disrupt the accounting space as their CPO.

“But why join someone else’s company when you’ve run your own successfully for 5 years?”

”But what about your 12 startups in 12 months mission?”

Below I’ll share 5 key questions I asked myself when making this tough decision - questions that may help you determine your next career move:

1/5 Am I Excited to Start Work on a Monday?

The main reason I paused Prod MBA after 4.5 successful years?

I got bored.

It was the same bootcamp.

Same workshops.

Same sales call format.

Same onboarding process.

That consistency was key - it’s why the whole thing worked - but it was also repetitive.

When I took a step back in January this year & asked myself, “am I exited to start work on Monday?”, the answer was a clear no.

So I reflected on what did excite me on a Monday morning.

The answer?

The challenge of building digital products. Specifically, doing the hands-on UX, UI & product strategy work to bring ideas to life.

My new role let’s me do this.

(I had discussions about a company acquiring Prod MBA, which could have led to new challenges, but it just didn’t excite me - & could have dragged on for 6-12 months with no successful sale.)

2/5 Am I Hungry Enough?

When I started the journey building 12 startups in 12 months in the summer, I felt that was the way to give myself a push - a kick up the a**.

The problem?

I wasn’t actually that hungry. After 5 years of solopreneurship, I was tired. I really needed a break. I needed a reset. And I jumped in too early, rather than taking a genuine sabbatical with the savings I put aside over the last few years.

The result?

I just didn’t have the drive I had 5 years again.

I didn’t have the need to make this work.

Without that need, I knew I wouldn’t have the obsessive focus & drive to get a business from zero to one.

(Note for parents: Having kids definitely makes starting a business harder. Not so much lack of time — I still get up at 5am to get focused work done before my son wakes up. It’s the lack of drive. Kids give you purpose, so you stop looking for that with your own career to some extent, which dampens down that fire we need to get a business up & running.)

3/5 Am I Surfing The Right Wave?

Startup success is ALL about right idea, right time.

Yet it is very hard to find the right idea at the right time.

Even OG Venture Capitalists like Marc Andreessen & Paul Graham admit that having the right idea at the right time is more important than the team, or even execution.

When I started working part-time with numra, I saw they were riding a big wave. Prospects queuing at the door for a sales call. More investor calls than they can handle. And a strong unique value prop to take over the accountancy market.

Accountancy = unsexy, but those are exactly the kind of under-the-radar markets I see huge opportunity in!

I’ve built 8 startups. 6 failed.

I know from experience it’s hard to find the right wave; so when I see one like this, I don’t want to miss it!

4/5 Am I Lonely?

5 years of solopreneurship was hugely valuable to me:

I’ve massively levelled up my product leadership skills, put away a good chunk of savings & have massive confidence in myself that I can build a business if needed.

BUT, it came at a cost.

It was lonely — even when I had an active family & social life.

All the decisions are on you.

You operate in silence most of the team.

Despite lots of client interactions, you still operate alone.

Freelancing with numra the last 3 months has reminded me that I get immense joy, belonging & purpose from working with a team.

5/5 What Would I Do If Today Was Day 1?

This question is about first principles.

About ignoring all previous commitments, ego, beliefs & expectation to get to the crux of what really matters.

For example, I struggled making the decision to join numra because I publicly committed to building 12 startups in 12 months.

Part of me feels like a failure - a fraud even - just throwing all that away. Letting people down. Having nothing successful to show.

But, when I put my ego aside, joining a startup was the right decision.

So that was the decision I knew I needed to take.

Anyway.

A bit of a ramble.

More giving myself clarity over my thinking than anything super valuable for you all, readers!

But these questions are important. And we need to ask them more often.

And they may lead to uncomfortable answers — for example, a client of mine ended up leaving a 20-year product career entirely to move into horticulture when asking similar questions.

But they will lead to a better quality of life.

And that’s what really matters.