Are you ready to begin again?

AI won’t ask how you’re doing. That’s why founders still need a village

Today we’re talking about starting a business a second time, and what happens when the ‘delusion bubble’ bursts…

But first, today’s highlights:

🛠️ We’ve built a toolbox for entrepreneurs who are starting again. It’s free (for now at least). More tools coming every week.

🎥 Our next Podcast episode is live! It’s a good one. Chris chats with Andrew Gunn, Co-founder and CTO at Mina Digital Ltd.

💡 Some wisdom from Rory Sutherland, with a great quote from Lenny Rachitsky: “First-time founders are obsessed with product, second-time founders are obsessed with distribution”

💸 Northern Powerhouse Fund and Praetura Ventures have announced the 2nd PraeSeed cohort of Northern Businesses.

Starting Again: Why You Shouldn’t Do It Alone

Starting a business is a bit like having your first child.

You go in wide‑eyed and full of hope. Everyone tells you it’s going to be hard, really hard, but you don’t believe it until you’re knee‑deep in sleepless nights and existential dread.

And still… it’s the best thing you’ve ever done.

The second time? It should be easier. You’ve been burned, you’ve learned. But the naive optimism has gone - it’s harder to fully commit to going again.

Steven Bartlett sums it up well in this post:

This is something we’ve seen from lots of founders we’ve spoken to recently.

The second time around you have the scars, you have the bruises, and maybe you have something different to prove.

You also suddenly don’t have the team around you.

Like bringing up a child, starting a business ‘takes a village’... but in business often we decide to go alone.

Especially now, solo founders are launching with tiny teams thanks to AI and automation. Efficient in theory, isolating in practice.

The emotional highs and lows are wild. Without people checking in and holding the mirror, it becomes overwhelming.

When I launched Trove in October, I was on my own. It was tough. Slower than I wanted. Heavier than I expected.

When Chris Dalrymple joined in March, everything changed.

Not just because we had more hands (well that did help!) but because we had different minds. Complementary skills. Shared momentum.

It’s easy to believe you have to be great at everything. Hustle harder. Stretch yourself. Push through.

But actually? You should spend your energy where you’re strongest. And surround yourself with people who make the rest easier.

So if you’re starting again—really starting—don’t just build an idea.

Build your team.

Employees, advisors, founder communities all help to spread the load and build the village that’s needed to help you succeed.

The right structure doesn’t just make execution easier, it makes endurance possible.

Introducing the iMVP Compass

If you are ready, start with alignment. That’s why we built the iMVP Compass — a simple but strategic tool from our Founder’s Toolbox that helps you:

  • Clarify what you actually want out of this next business

  • Pressure test your idea across four critical lenses (Desire, Demand, Delivery, Durability)

  • Avoid building a business that looks good on LinkedIn but feels bad on Monday

See you same time next week.

Carl.