You don’t have to figure it all out alone

When I started GuessWorks, I thought being a ‘good’ founder meant figuring everything out on my own. After all, it’s my vision, my business, my responsibility… right?

So I read all the books. Listened to all the podcasts. Spent hours Googling things that, in hindsight, I should’ve just asked someone who actually knew. I was so caught up in proving I could do it myself that I wasted months overcomplicating things that could’ve been sorted in a 10-minute conversation.

The biggest shift? Realising that asking for help isn’t a sign of weakness - it’s a business strategy. Founders aren’t meant to be one-person encyclopaedias. The best ones ask, delegate, and collaborate as much as they build.

So if you’re sitting on something right now - an idea, a challenge, a bottleneck - who could you ask for help? Because trust me, doing it alone is overrated.

Founder cheat sheet

Before you spend hours (or weeks) spiraling in your own head about what to do next, try running your decision past these three people:

The ‘Done It Before’ Person – Someone who’s already faced this exact challenge and can save you from making rookie mistakes. Could be a mentor, a peer, or just someone one step ahead of you.

The ‘No Bullsh*t’ Friend – Someone who isn’t invested in your business but will give you a brutally honest take. (Because sometimes, we don’t need more encouragement—we need a reality check.)

Your Ideal Customer/User – The people you are building for. Instead of guessing, just ask them: Would you use this? Would you pay for it? What’s missing? Their insights will tell you more than any strategy framework ever could.