Category Archives: Bootstrapping

What is a hustler?

“Birthdays was the worst days, now I sip champagne when I’m thirstay…”

“Birthdays was the worst days, now I sip champagne when I’m thirstay…”

Hustler can mean a lot of things. For many people, it’s a pejorative term.

In the 1993 rap hit, “Juicy”, Biggie Smalls talks about how he was forced to hustle on the streets in order to support his baby daughter. So for some, a hustler is a criminal.

When I was in third grade playing soccer, my coach used to scream at me to show more hustle during practice because I was so lazy. This is my personal negative association with the term, of being forced to hustle at soccer practice when I could have been at home playing video games on Saturdays (I had different problems than Biggie).

But today I love the word hustler. In fact, it is one of the greatest compliments I can give to someone. In the startup world, a hustler is someone who doesn’t let fear get in her way. Even when she’s in over her head, lacking a certain skill or network, she puts her head down, learns what she needs to learn, and succeeds no matter what. This is a resourceful character trait that I look for in all people I want to do business with.

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How Chris Dixon helped me handle Fear

Thanks dude!

Thanks Chris!

Oh shit.

That’s all I could blurt out. I was at the ATM staring at my Chase business checking account balance and the number staring back at me was $500.

Oh shit.

An $8,000 bill that my business owed was scheduled to post tomorrow. Earlier in the day, I hounded a client about a slightly late payment they owed for a big marketing campaign. The VP I spoke to curtly assured me that the payment would arrive the next day.

Oh shit.

Running through the logistics in my head, the mailman arrived at my office every day around 3:00 PM. That gave me about two hours to collect the client check (assuming that it indeed would arrive) and deposit it in the bank. If the $8,000 bill posted at the end of the day, I’d be okay. If it posted earlier, then I’d now have to deal with a bounced check, which was sure to create headaches for the line of credit I had applied for at Chase…

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My pathetic Profit & Loss Statement from 2006

This is a snail

Photo source: Wikipedia

Businesses take time to grow.

What I hate about Silicon Valley is that this ecosystem puts a lot of pressure on entrepreneurs to grow their companies at unnaturally fast speeds, across all dimensions: user acquisition, headcount, revenue, even expenses.

I’m not saying that growth is bad. But I do believe that more often than not, a slower and more deliberate pace of growth early on can set an entrepreneur up for success later on.

What is the root cause of this pre-mature growth pressure among founders? It’s investors. When you raise money, you buy into a rat race that compels you to show progress toward a huge ROI for your investors. Some investors are patient, but many are not and want to see fast returns on their investment in a startup, pressuring founders to raise more funds or take quick exits. The way to get to higher valuations fast for the investor is fast growth.

I chose to bootstrap my last startup because I didn’t want to deal with investor pressure. I wanted to grow organically, at a speed that I dictated.

Today I’m proud to say that my company pulls in substantial revenue and is highly profitable. But the earliest days were ridiculously modest in terms of performance. The following screenshot is my company’s actual Profit & Loss Statement from 2006. Keep in mind this is eighteen months after I started my startup:

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