How do you compete in a crowded market when you have raised zero dollars?
Nathan Barry, ConvertKit CEO, talks about how he has bootstrapped an idea to $30M in ARR.
Plus, he breaks down his step by step roadmap to building wealth. (See his Ladders of Wealth Creation framework.)
In this episode we discuss:
- Nathan’s explains his framework: Ladders of Wealth Creation
- Should you start something yourself or acquire a business
- Why you should focus on a small niche when competing against a powerful incumbent
- How he has grown ConvertKit from idea to $30M MRR
- How he approaches capital allocation and leverage as a bootstrapped owner
- How to attract talented people when you have less money to offer
- What aged well and what didn’t with Nathan’s book Authority
Also, want to see how I got Nathan as a guest?
Check out our negotiation in the Twitter DMs.

Okay, here are five things that caught my attention.
💡The Minimum Viable Testing Process for Evaluating Startup Ideas
When validating an idea, most people default to the principles of Lean Startup – do some customer research, throw an MVP out there as fast as possible, and hope it hits.
Instead of building a MVP try a MVT (Minimum Viable Test) like the CEO of Maven did. Here are some takeaways:
- Find your value proposition
- List your risky assumptions
- Test the atomic unit (For Amazon, it’s ordering a book online.)
- Nail what your customer cares about
📧 12 Examples of Drool-Worthy Welcome Email Series for D2C Brands
Having people subscribe to your email list is a big step in getting them to purchase, but there’s more work to be done.
You’re automated welcome flow could make or break how consumers view your brand. Here are some innovative ideas
- Mack Weldon– They do text based email from an actual person.
- Toms – They focus on the mission and the story of the founder.
- Wynd – A 3 email series that gives you a free product right away.
🤔 8 Things Every Non-Technical Founder Should Know How to Do
In the technical world, non-technical founders risk being seen as unqualified. “You can’t build a software business if you can’t make software.” That’s not true.
But, you do need other skills. Here are the traits you need according to one non-technical founder:
- Skills around researching and validating concepts
- Ability to give bulletproof feedback
- Ability to not just sell, but pre-sell
- Be the #1 Cheerleader
✔️160 Startup Ideas from the Trends Website [DATABASE]
Thinking of startup ideas? The Trends site published 160 startups they would start based on insights they found over the past year. Here are some of my favorite ideas:
- Start your own mobile carwash service (Seriously, I need this bc my two girls trash my car on a daily basis.)
- Wearables that can measure fertility and pregnancy hormones directly from users’ blood
- Create specialized job boards to help childcare businesses hire well
- DNA-based personalized supplements
- Create a mental fitness health club
- An online marketplace (like ThredUp) for used furniture
⏰Finally, a Productivity Tool that Merges Your Calendar and Your Tasks
To truly be productive, it’s not about your to-do list. It’s about your calendar. This is a YC-backed startup that’s working to create a beautiful marriage between your Google calendar and your project mgmt tool.
My partner, Yonathan (a productivity ninja), is putting it to the test to see if we should use it.
Want more content like this? Join my email list or listen to my podcast, If I Was Starting Today.