The Third Time Around, Is It Easier?

On this episode Abadesi talks to Waseem Daher, founder and CEO of Pilot. Pilot is bringing bookkeeping into the modern age. He has started (and sold!) two other companies prior to Pilot.

In this episode they talk about...

The story of starting Pilot and what Waseem learned from his two previous companies

“The end-to-end solution is really what made the business work. We are going to be your bookkeeper, your finance team, rather than sell you software.”

The story of Pilot goes back to his first company, where they tried to do their books themselves, but realized how tedious it was and how much could be automated.

He explains why he tries to have a more focused approach to company-building now:

“I try to have a better sense of what is actually important. We were so worried about all of the stuff that we thought represented an existential threat but in practice literally zero of those things mattered. Of all the things I remember agonizing about, none of them had any actual effect on the business.”

He also says that he makes sure to take time to rest and recharge, rather than working all the time:

“In the first company we worked all the time, 6 days a week, 12 hours a day. Despite having worked that long, there were Saturdays where I still felt behind so I worked then as well, and every time I did that, it was always a mistake.”

When it makes sense to take venture capital versus bootstrap a business

“There’s a very pervasive and harmful narrative in Silicon Valley that the VC way is the only way to do it. I actually think the VC way is the unnecessarily difficult or hard way.”

Waseem explains how to think about starting a company and talks about the principles to keep in mind when you’re thinking about the risk and reward of different approaches:

“If your objective is wealth creation, you should not start a startup, you should go work on Wall Street or something. The easiest way to make $10M is to own 100% of a company that’s worth $10M, not to own 1% of a company that’s worth $1B.”

He says that “lifestyle is not a bad word” and that as a founder you don’t need to care about serving a massive market unless you’ve taken venture capital funding.

“Venture capital is not right for 99% of businesses. You have to be building something that is targeting a gigantic market to have a company worth billions of dollars doing hundreds of millions of dollars of revenue.”

How to think about a potential acquisition

“By raising a bunch of institutional capital, you’re prevented from taking exits that are otherwise very good or very profitable.”

Waseem shares what he’s learned from two previous exits, one to Oracle and the other to Dropbox. He says that it’s most important to think about how you and your company will mesh with the acquirer and choose the offer that provides the best fit rather than the highest dollar amount. He says that if the fit is good, you will create much more value through the relationship together than the value of the acquisition.

“Look at the acquisition as the start of a new relationship, not the end of something.”

How Waseem stays productive

He explains that he keeps most of his apps on his phone in folders rather than on his home screen. This creates friction and ensures that he has to be intentional about what exactly he is doing when he takes out his phone.

He also explains exactly how to write emails that get responses from busy people:

“Craft something that is really short, that is to the point, and that has a very crisp and clear call-to-action at the end of the email. Ideally the call-to-action is as easy to respond to as possible.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 😸