So just some hacks to potentially make it easier:

• Start with SMBs. It’s easier to get taken seriously, not just as a CEO, but also as a company, with smaller businesses. They close faster, make quicker decisions, and the owners take the risks. The more gatekeepers there are, the more decision-makers, the harder it can be to break through. You may get 1 or 2 bigger customers, but don’t start in the enterprise unless you know the enterprise, 95 times out of 100.

• Be always on the front lines. Do all the sales, customer support, post-sales yourself, as much as you can. Secret: Customers LOVE to talk to the CEO. Even the CEO of a 2-person company. Even an 18-year-old CEO.

• 12 months after closing your first customers, you’ll be the best there is at your market and product. And you’ll just keep getting better. You will get so much better. You will be so experienced once you have 10, 15, 100 customers, 1000 users, under your belt. You may Know Nothing now but in 12 months you’ll be an expert. Just watch.  So hang in there, listen, learn and you’ll get great.

• Be respectful & Don’t Pretend who you (as CEO) are. You can pretend just a little bit that the product does more than it does. But don’t pretend you are so much more experienced than you are. Don’t pretend you’ve been in business longer than you have been (Everyone does this.  Don’t do this). The early adopter customers are looking not just to buy today, but to buy into you. And they know they are taking a risk. Lead them with truth, knowledge, and enthusiasm. Not everyone will take the risk on the next Gates or  Levie or Zuck. But some will.  It usually turns out just fine.

(note: an updated SaaStr Classic post)