You gotta spend money to make money

Welcome to the first edition of Too Many Tabs — my weekly thoughts on building, breaking, and learning as a founder. I’m the co-founder of Poppylist, and this newsletter is where I unpack what we’re doing behind the scenes — the messy middle of startups. No playbook, just process.

A couple weeks ago, Sarah (my co-founder) and I took Poppylist to the ABC Kids Expo in Las Vegas — basically the CES for baby products.

We introduced Poppylist to hundreds of new brands, discovered some wild innovations in the space, and strengthened relationships with existing partners.

But the most valuable thing we did wasn’t on the expo floor.

We hosted a private dinner.

It wasn’t cheap. Especially not for a bootstrapped startup. But it worked.

We invited two dozen founders, retailers, and industry thought leaders we wanted deeper relationships with. No pitch decks. No panels. Just good food and honest conversation.

We left that dinner with tighter connections, better feedback, and —here’s the kicker—sponsorship deals that more than paid for the cost of the dinner.

For most of our journey, we’ve been allergic to spending money unless we had to. That’s still our default. But this was a solid reminder that sometimes the fastest path to growth isn’t a new feature or ad campaign — it’s investing in relationships.

Not every bet will pay off. We’ve made others that haven’t. But this one did — and it’s shifted how we think about spending.

Bootstrapping doesn’t mean starving your growth strategy.

It means being strategic with how — and where — you place your bets.