The 10 Things I’d Tell My Younger CEO Self to Do Better Next Time

You have to move fast and break things, but if the pit in your stomach says, “Maybe don’t do that” — slow that decision down.

Ah your top unforced errors. They haunt you, as time goes on.

What are the Top 10 things I’d tell myself to do better, if I could go back in time?

My top list:

• Slow down big decisions — when you aren’t sure. You have to move fast and break things, but if the pit in your stomach says, “Maybe don’t do that” — slow that decision down. My biggest mistakes have been where I quickly said, “Roll the dice,” but my gut wasn’t sure the downside risk was worth it.

• Budget an extra 6–12 months beyond the longest timeframe you have budgeted. We raised 18 months of seed money. We needed 30, or at least 24, months to get to a true business. It always takes longer. More here.

• Slow down the initial team formation phase if you don’t have it right. Fire fast doesn’t work so well with co-founders. No one has a perfect team to start, or ever. But if the initial team’s goals aren’t aligned … that never gets fixed. It’s OK to wait another 3 months to say GO if that means the team is stronger.

• Charge from Day 1. Free users and “free customers” can do incredible things for you, if you are running a freemium playbook. But they also provide terrible, distracting feedback if you aren’t also getting feedback from folks that convert to paid. Free users who haven’t converted to paid give you product feedback that is rarely consistent with what paid customers ask for. More here.

• Pay Up. Even when cash is tight, paying an extra $20k a year or more for a resource that is 2x-5x better is the best investment you will ever make. Hire a real stretch VP to own marketing, sales, etc. — not a low-level more junior hire. Find a way. More here.

• Charge more. Your product either has value or it doesn’t. Charging 20%-50%-100% more than you’d planned will help you learn that faster, and get to a viable business faster. Don’t charge less to get the ball rolling. That only helps with commodities. More here.

• Move on from anyone that isn’t 100% customer-centric. Later, not everyone has to care about customers. But in the early days, everyone has to. They will let the whole company down in SaaS if they aren’t. Folks that aren’t on the customer journey you are on should find a new home.

• Resolve founder conflict. Founder conflict kills start-ups, though often slowly. You have to fix this early.

• Pay yourself as soon as you can. Working for free is OK in the early days, but later, it gives you an excuse to just “do your best.” Your best isn’t good enough. Winning the market is good enough. More here.

• Get better mentors — and pay them. You haven’t done it all before, at least not everything. And even if your mentors are centimillionaires — pay them (at least in equity). A so-so mentor or advisor is, in the end, a waste of time. But 1 or 2 folks that can truly help you think through the tough decisions — they are worth their weight in gold. More here.

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