June is a busy month: my wife just started a new job, school is winding down for all my kids, my eldest son is graduating grade 12, my daughter is visiting us from college... and today is my birthday! (1980 baby) 🥳

Here are a few things I've been thinking about:

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The opportunity cost of bootstrapping

Even if you're not investing a lot of money in your business, bootstrapping is a financial risk. You're gambling some of the best years of your career to make a bet that might not work out.

I think it's healthy to reflect on whether the market/idea you're pursuing is worth the risk/investment. Essentially, founders need to learn how to identify if they're investing in the wrong thing and know when it's time to move on.

On the Indie Life podcast, Dagobert Renouf explained to James McKinven why he and his wife decided to give up on their startup:

Many indie founders start businesses in pursuit of freedom: choosing where they live, setting their own schedules, and more.

But the only thing that can sustain that lifestyle is a business with a solid financial engine.

Essentially, true freedom happens when you have a strong financial engine that empowers you to live life on your own terms.

If you've been struggling, and need advice on knowing when (or if) to move on, read: "When you should quit".

Have thoughts? Reply to this email, or reply on twitter, mastodon, bluesky.

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Good podcast episodes:

• Tara McMullin: "Maybe bigger isn't better?"​
• Hammerstone: "Colleen is pumped"​
• Hackers Inc: "How to be a manager and still code"​

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🙏 Help requested:

Want to give me a little birthday gift? 🎁

• Search for "how to start a podcast" or "podcast hosting" and click on the first Transistor link you see. 😉
• Even better: recommend our "how to start a podcast" guide to your friends.
• I've been writing this blog post draft for almost a year. Should I publish it? How can I make it better?

Have a great Saturday!

Cheers,
Justin Jackson
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🐘 Follow me on Mastodon​
🔵 Follow me on Bluesky​
🐦 Follow me on Twitter
⚡ Join the bootstrapper community on MegaMaker ​

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