Thread by @Shpigford

1/ It's fun (or, more specifically, "therapeutic") to reflect on learnings over the years for businessing.

15+ years in to all this, I'm still winging it on just about every level possible, so take these insights/observations for what they're worth.

2/ Hire/outsource finances immediately. Founders are eternal optimists and every new feature/deal will turn things around. Except...they won't. And you need a realistic to keep tabs on your books and help keep you from going out of business.

3/ Resist the urge to hire. If you’ve raised any amount of money, you’ll have a deep burning desire to go hire people. But resist it. If you cut back on superfluous things and hyper-focus on needle-moving tasks, you can do an unbelievable amount with a small team.

4/ Needing to fire someone is a failure on your part, not the person you had to let go.

5/ “Busy” does not equal “productive”. You shouldn’t be doing 1,000 different things. Business isn’t that complicated. Very few things are urgent. Very few things actually even need to get done. As a founder, pick just 1 or 2 “must do” things each day.

6/ Focus on your strengths, delegate your weaknesses.

I’m a learner. I love learning new things. If I give myself enough time/space, I can generally learn just about anything on some level. The problem is that I arrogantly think I can make anything a “strength”. False.

7/ Maintain the power to walk away. Negotiating some business deal? Thinking of raising money? Always maintain the power to walk away. If you ever are in a position to critically needsomething, you’ll come out on the very bad end of that deal.

8/ Investors are great for company optimization & scaling, less so for product advice. Don’t assume investors have answers for everything. They’ve got a specific skill set around growing companies but are generally less useful when it comes to actual product decisions.

9/ You’ll burn through all of your funding in a year. No matter how much you raise, you’ll burn through all the funding in 12–18 months.

10/ Ignore data early on. If you’ve just launched your product, the phrase “A/B testing” should not be in your vocabulary. You simply will not have enough traffic or conversions for statistical significance.

11/ Ignore your competition. It’s so easy to fall in to the habit of checking up on what your competition is doing. But here’s the problem: doing this puts you perpetually one step behind. It makes you reactive instead of proactive.

12/ Don’t build internal tools. The danger in building internal tools is not that it saves an insignificant amount of cash, but that it stifles future growth.

13/ Don’t wait to charge. You’re not running a charity. Charge from day one.

14/ User action is much more relevant than user feedback. Feedback from users is great for understanding their line of thinking, but not great for understanding what they’ll actually do. Many times their actions don’t line up to their words. You need both to get the full picture.

15/ A $9/mo customer is an entirely different customer than a $99/mo customer. All price points are not create equal. Low-ARPU customers are not only the most price-conscious, they’re almost universally the neediest. Support costs alone can run you in to the ground.

16/ Don’t lower prices, raise value. If your gut feeling is that you’re priced too high, then raise the value of your product to make it worth it. There’s essentially no ceiling on raising prices, but you’ll quickly find yourself hitting the floor compete on pricing.

17/ Sales solves all things. Almost any business problem you’re having is solved by selling more of your product. Not by making product improvements or getting company t-shirts and stickers, but by going out and making sales happen.

18/ Sell painkillers not vitamins. If you’re just a “nice-to-have” then the hole in the bucket will always leak faster than you can refill it.

19/ Talk to your customers. With words. Out of your mouth. Get on the phone with every single customer who signs up, upgrades, downgrades & cancels. Actually talk to them as humans do. It’s important to have a conversation as it gives you more honest insights in to what they did.

20/ The Next Feature Fallacy is real and will cloud your thinking dramatically. Like it or not, that next feature that you’re so excited about will categorically, as an individual unit, do nothing for your business. But man if we don’t like to think it will.

21/ Don’t build solutions in search of a problem. Just because you had an idea doesn’t mean someone needs it. The mere existence of a solution doesn’t validate the existence of a problem.

22/ You will never attain the perfect product. The effort required to “polish” a product has diminishing returns. Yes, the details matter. But “shipped” is better than “perfect”. Startup graveyards are littered with companies who never actually launched anything at all.

23/ Many times you have a distribution problem, not a product problem. As makers we think we can build our way to success, but the reality is you have to sell and market your way to success.

24/ Startups are like kids. No matter what you do to try and control for all the variables, at the end of the day your startup is going to do what it’s going to do. Don’t beat yourself up when you make mistakes.

25/ Optimism is a crutch. Be a little doom ‘n gloom. Run through worst-case scenarios on a regular basis and understand how rough patches could play out.

26/ Get friends who aren’t entrepreneurs. The startup echo chamber is real and dangerous and real dangerous. Surround yourself with people who are completely different than you.

27/ Vacations are crucial. Taking time off not only helps you stay healthy, but it also makes you a better founder. It clears your head, helps you focus and snaps you out of your tendencies to over-focus on your business.

28/ Don’t attach your own self-worth to your company. An unbelievable number of founders I know (myself included) have struggled with depression or anxiety. It’s very easy to think of yourself and your startup as a single entity, but you are so much more than your company.

29/ Everybody is winging it. Every. Single. Person. Nobody actually knows what they’re doing. Sure, they may have hindsight on things that worked in the past, but right now? Nope. They have no idea.