Hey, Paul! I’m always surprised by how little I know about anything. No matter how much you read, how much advice you listen to, or how hard you try to imagine multiple scenarios when making decisions, I realize that you can learn only by doing. This sounds very cliché, but it is what it is.
When you work for somebody, you are limited in what you can do, so learning happens less often or is narrower. When you are running a company, however, you have a bias toward action. You have to do most things in the beginning, which means you do more, fail more, succeed more, and ultimately learn more, faster.
Running a business stretches you in ways you can’t predict. It’s a self-discovery process that I never experienced in any other job, no matter how much responsibility I had.
I’ve been surprised by the fact that even when you try to avoid silly mistakes, you can still make them and not even realize it. For example, everybody says: “Hire slow, and fire fast.” I knew this very well, but every time I had to fire somebody, I would somehow delay it and regret that it took too long.
I’m still surprised about how slow and bureaucratic companies are. Even the tech darlings that everybody loves can operate like government agencies sometimes.
I’m still surprised about many things, and I hope this continues to happen. To me, it means that I’m learning.
If I have to give any advice to anybody who wants to start a software as a service business, this would be:
- Try not to raise money from traditional VCs. Plenty of new alternatives are available out there.
- Be an example for your team. Do not expect anything from anybody that you are not willing to give yourself.
- Find a therapist or coach, probably both if you can afford it. Your mind and emotions will be the biggest challenge—not the business.
- Learn how to talk to customers. It’s not enough to talk to them, though; you need to know what to ask and how to interpret what they say. Make the best of each conversation. Listen, and forget about your ego.
- If you are not technical, as in being able to code, learn how the sausage is made. You will have much better conversations and the ability to lead product development efforts more effectively.
- Try a lot of things quickly, but don’t be reckless. This one is hard. You will understand the balance with time.
- Try to understand the difference between persistence and idiocy. I still don’t know it.
- Be good to people; your reputation and relationships will survive beyond your business.
- Don’t lie to yourself. Pursue the facts with optimism.
- Unfortunately, most stereotypes about lawyers and accountants are true. Find good people who understand your space, and constantly remind them that you need them to translate what they do in plain English so that you can make better decisions.
- Related to the above, if you don’t understand something, ask as many times as needed. Looking stupid is better than being stupid.
I can spend all day adding stuff to this list =)