Hi friend!

Building in community is something I've always highly valued, but in the last couple weeks I realized I haven't been prioritizing it as much as I should have. I went to ConvertKit's Craft & Commerce event a couple weeks ago and that has turned out to be one of the most helpful activities I'll do all year.

Because of learnings from that conference, I'm tweaking this newsletter slightly.

I'm going to stay focused on bootstrapped ventures. That won't change. However, I'm going to pivot the content into deep dives about how bootstrapped ventures got their first $250k in revenue.

Why $250k? The first steps of starting a venture tend to be the hardest and $250k almost allows anyone to go full time on a venture.

If you have thoughts on this pivot, I'm open to feedback!

Here's this week's deep dive:

Today, Nathan Barry is the CEO and founder of ConvertKit soon to be Kit. Today, ConvertKit makes over $40 million in annual revenue, has over 80 full time employees around the world, and is completely bootstrapped.

There’s a lot of cool stories about how ConvertKit became what it is, but the story I want to focus on is Nathan’s journey from full time employee to creator.

This is a journey that Nathan was pretty public about on his blog post and I spent about 20 hours going through all of it so you can potentially implement some of the strategies Nathan used to create his $256,000 business.

Helpful Content from Others:

​Head of Instagram: Adam Mosseri Interview​

This interview by Colin & Samir was incredible. If growing any audience or following on Instagram is of interest to you, this was a wonderful behind the scenes. I've heard a lot about how social media companies are shifting from social graphs to interest graphs because of TikTok. I learned a ton from this interview.

Another newsletter you should check out:

Upcoming Events:

All times are in EST. Submit an event or opportunity here.​

​Overcoming the Five Deadly Sins of Strategy​

Wednesday, June 26th from 12:15pm on Zoom​
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Does it feel like your OKR’s are being achieved, but nothing changes? Do you look back a year and feel the company is exactly the same?
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Why is that?
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Often, strategy isn’t operationalized properly because of “The Five Deadly Sins.”
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These issues stem from a failure to set your team up for success using strategic, data-informed, and politically safe methods.
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This workshop, Overcoming the Five Deadly Sins, is designed to help you, both as someone who has to create and often follow strategy, learn how to identify and adjust your team's processes to turn a dead strategy into an alive one.

Thanks for reading!

Matt

P.S. Looking for recommendations on software or content? Check out my personal recs here.​