Justin Jackson

Justin Jackson

Intro

Justin Jackson is the co-founder of Transistor.fm, a successful bootstrapped podcast hosting company. The journey building Transistor were documented on the Build Your SaaS podcast, which is a must listen. Justin is the founder of the MegaMaker community which he started in 2013, so if you're part of the maker sphere - you'll probably have heard of him.

13,000

Talking points

On building Transistor.fm

  • Why a podcast host?
  • Open startups vs closed. Point where the downsides start outweighing the benefits.
  • Surprising thing. Most enjoyable / least enjoyable.
  • What's the end goal? Do you want to sell or having fun?
    • Simplecast exit

On paying yourself as a founder / managing money

  • Saw you were recording a podcast with Marie Poulin (she was episode 20) about managing your finances as an indie hacker. Creator Economics.
  • What's the biggest challenge most run into?
  • Comparisonitis. "This bootstrapper is making $XX p/m, so must be better than me"
  • What's the magic number for most?
    • Founders might be happy with $100k p/y, but you could get a Shopify job for $200k pr a FAANG for like $3-500k p/y. Without all the stress of being a founder. How do you choose.
    • Daniel Vassallo going from $500k Amazon job, to much less with his own projects but having more freedom.
  • Thoughts on people eating through their savings while bootstrapping

On mental health as a founder

  • I've had my own struggles with this, especially with this latest UK lockdown. I'm finding it hard to motivate myself and stay consistent. I know you've also faced similar mental health challenges. I don't think it's spoken about enough.
  • What can founders do to look after themselves more?
  • How to avoid burnout situations?
  • Dealing with self-doubt. See comparisonitus above.

General bootstrapper questions

  • Quite boring, usual stuff. Might avoid this but stuff to talk about if we run out of things.
  • Validating your idea.
  • Choosing a market / niche. Can it work if it's saturated?
  • Advice for founders starting out.

Recommendations

  • Book - Life Profitability
  • Podcast - Software Social
  • Indie Hacker - Derick Sivers