TMBA480: Thoughts on Funding Options for Bootstrappers with Rob Walling

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A few weeks ago, Dan and Ian had a conversation on this podcast where they shared some of their feelings about venture capital.

This is an important topic to a lot of entrepreneurs, and it’s one that we plan to cover a lot more throughout 2019.

Some of the opinions we shared in that episode were rather controversial. Several of our listeners actually called us out on being a little bit vague about our thoughts, and we thought it was a good chance to revisit the topic.

One of the people that reached out to us about that episode was Rob Walling.

Rob is someone who should be very familiar to the listeners of this show.

He hosts one of our favorite podcasts, Startups for the Rest of Us, organizes his own annual conference called MicroConf, and has previously owned and sold several startups, including a Software-as-a-Service company called Drip.

Rob has also recently started his own startup accelerator fund called TinySeed, which is specifically designed to help bootstrappers grow their businesses.

On today’s show, Rob has joined us to share his thoughts about venture capital, bootstrapping, and what he hopes to accomplish with TinySeed.


Listen to this week’s show and learn:

  • Rob’s 9-year journey to financial independence. (3:12)
  • What TinySeed is and why Rob decided to start his own accelerator. (12:10)
  • The true value of mentorship. (31:47)
  • Specific scenarios where a bootstrapper might want to seek funding. (37:20)
  • Why Rob believes in investing rather than buying businesses outright. (49:28)

Mentioned in the episode:

This week’s sponsor:

This week’s episode is brought to you by Dynamite Jobs. Dynamite Jobs is a service that helps entrepreneurs and listeners of this show find top, experienced talent to join their teams.  These types of remote positions can be especially challenging to hire for, and we specialize in making that process easy.  For those of you who are on the hunt for a new opportunity, we know how frustrating it can be to find good remote jobs, so we only work with established, reputable companies offering great remote opportunities. If you’re looking for a new job in the new year, check out

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST. Cheers, Dan & Ian