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Question and Answer with Rob Walling

Rob Walling

Serial entrepreneur, author, angel. Founder of tinyseed.com, MicroConf, Drip. Author of Start Small, Stay Small.

Minneapolis, MN
Rob Walling

What's the most important thing you think attendees should do?

Ship something, and make it a habit to ship something every day.

What mistakes do people make in the early days?

I think it's important to be okay going off the beaten path and go against common wisdom.

What was your first business?

I launched a bunch of things that failed over five years, back when Joel Spolsky was the only person blogging about this. Starting with failure doesn't predict a future of failure. My first real business was DotNetInvoice.

Which comic book do you buy the most?

One of my first businesses in high school was selling comic books. After I sold Drip, I had enough money to buy fun investments like Bitcoin and first edition comic books. Spiderman #250 is one of my favorites.

Did you know after Drip what would be next for you?

I didn't - I wanted to take time off and had no idea what was next. I took six weeks off before I started thinking about Tinyseed.

Does Tinyseed feel as stressful as Drip did in the early days?

It's way less stressful and quicker to build. I'm chasing the next challenge. You don't want to do the same thing - building a SaaS - multiple times. It gets boring.

What's your zone of genius?

Trend spotting?

It might be just showing up for a long time. 430 podcast episodes, 18 conferences, the slog of Drip, etc.

What's your criteria for TinySeed?

The founder is most important, then the traction of the product, and then the product itself.

There are stereotypically successful founders that grind it out, others that are very quiet and show up every day, and others that are experts in specific areas.

How do you fight the cognitive bias of finding people like you?

I don't think I'm the best founder, so I'm actually looking for people different from me.

What do you think kept you from reaching success faster?

Fear. I was too scared to send cold emails, introduce myself at conferences, or speak on stage.

Overrated Underrated

  • chat bots: short term overrated, long term underrated, similar to cryptocurrency
  • las vegas: overrated. Hopefully next year it won't be in vegas! We do it here for cost reasons. It would be about $200 more expensive per ticket.
  • paid ads: underrated. Not enough people take advantage of paid ads. Once you get that engine going it's super cool.
  • twitter: overrated. I've wanted to quit for 3 years but keep getting pulled back. There's no nuance for an actual conversation.
  • batman: underrated. Lego Batman is super cool.

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