The Bootstrapped Founder

We've been taught to believe that creators are only truly successful when they reach the top echelon of their platform, with millions of followers and likes. But this is a false notion that doesn't accurately reflect what success looks like for creators — or what “success” is about in the first place.

The truth is that success for creators comes in many different forms, and it usually doesn’t depend on reaching the top of the platform. There are many creators who have found success by building a loyal and engaged audience in a very specific niche, even if they “only” have a few thousand followers. These creators have found ways to meaningfully connect with their audience and provide value to them, which is what ultimately leads to success.

- Avoid Vanity Metrics
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

I am talking to Rosie Sherry, proprietor of Rosieland and community empowerment expert. She runs her own communities, monetizing a few of them, and has been managing the IndieHackers community in the past. Rosie is an expert all things community and education. And that's precisely what we'll talk about today.

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.

There is a huge difference between building a product, a business, and a company. It's a progression from one to the other, usually involving making significant changes in your life. Requirements change, and so does our lifestyle to make our dreams possible.

Ideally, we have a master plan on how to get there.

But in reality, we have to pay bills, take care of our family, and deal with the often unexpected hardships of life.

And while everyone's situation is unique, many entrepreneurs have found ways to finance their business-building journeys and make ends meet. That's what we'll be talking about today.

- Paying the Bills With Your First Indie Business
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

Today, I am talking to Jakob Greenfeld. I’ve been reading Jakobs blog posts for years now, and they’re as spicy as they’re thoughtful. There’s not a single post on there that feels unfinished. That’s quite impressive. Well, I think we’ll figure out why that is during our conversation. We’ll also chat about how to unlock critical thinking by writing and what it means to give yourself permission to do things your way.

Here’s Jakob Greenfeld.

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.

In my conversation with Daniel Vassallo this week, I learned that Daniel uses social media —Twitter in particular— to find inspiration for his own work as a teacher and content creator. Intentionally doomscrolling Twitter to come up with writing prompts and business ideas? Why not!

If we consider this a strategic effort, not just wasting our time on social media, let's develop a few frameworks that lead to more tangible results.

Today, I want to talk about finding ideas, problems, and points of tension that hint at practical business opportunities on social media.

- Find Business Ideas on Social Media
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

Today, I am talking to Daniel Vassallo, writer, founder, and person with very strong opinions. He is building a portfolio of small bets in public, on Twitter. I will talk to him about the importance of making money in diversified ways, how to structure your life around being a founder, and how to figure out which business ideas might actually work.

Here is Daniel Vassallo.

What is the lifetime value of a subscription business? 1:12

Different kinds of software fit different pricing models. 5:04

What is a portfolio of small bets? 9:30

Business is unpredictable. You need to radically reduce the input. 13:48

What common things do you share with other entrepreneurs? 17:46

Don’t try to be too novel. 21:31

What’s a good approach to spreading out your experiments? 26:14

What is the best price for your business? 40:08

How Pieter Levels’ portfolio has changed over time. 45:58

How you can use social media to get new ideas. 51:26

Sometimes it’s something seemingly unrelated that opens your eyes to a new way of doing things. 55:01

Links:
- Daniel's Revenue/Days on Market graph.

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.

I was talking to Damon Chen, who built Testimonial.to to $400.000 in ARR this week, and at one point, he mentioned that he isn’t looking into selling his business just yet. Maybe even never.
That got me thinking.

While we all want to build sellable businesses, is there such a thing as selling too early? How can we determine when that phase ends and when it’s time to get acquired? Should we even do that, ever?

Let’s look into why we might want to hold on to our business even when acquirers come knocking.

And by the way, if you’re just starting out on your founder journey and you think that this would be a nice champagne problem to have, don’t underestimate having these things figured out in advance.

- Why You Shouldn’t Sell Your Business
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

Today, I am talking to Damon Chen, the founder behind Testimonial.to, a social proof tool that has recently reached $400.000 in annual recurring revenue. Now that’s extremely impressive, particularly considering that Damon got it there all by himself.

So, let’s just ask him how this family man accomplished such growth while living in one of the most expensive places you could build a business in. Here’s Damon Chen.

LonelyDev is a community that I built to solve my own problem. 1:01

Lonely Dev turned into IndieLog. 4:09

How to get out of a full-time job to start a business. 12:55

Why you need to be healthy and whole to be able to build a good business. 19:33

Why you need to add video reviews to your landing page. 26:31

Video and authenticity 31:30

There is a point where you reach saturation and you need help. 36:20

What is your exit plan for your business? 42:27

The importance of having a good exit strategy. 47:18

The importance of having a community to support bootstrappers. 51:16

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.

Earlier this week, I talked to Michele Hansen of Geocodio on The Bootstrapped Founder Podcast. Michele co-founded the business with her husband and ran it as a side project for several years. Now, that's a long time to wait before you commit full-time to a project. We also learned during our conversation that there are many ways of determining when the right time is to make that leap: for me, it was reaching a specific revenue figure, and for Michele, it was something else entirely.

So let's explore this critical step today. When should you go from side-project to full-time? What are the significant catalysts that speed up this process?

- When Should You Go from Side-Project to Full-Time?
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

I am talking to Michele Hansen, the co-founder of Geocodio, an indie SaaS business in the world of mapping and geolocation. I've been a fan of her work, both as a founder and as an active member of the Indie Hacker community for years now.

I followed her journey with the business just as much as her foray into writing her first book, Deploy Empathy. Michelle really gets the founder community, and she's a respected teacher of all things customer development.

In this episode, we chat about finding the right time to commit to a business, learning when to say no, finding your niche, and learning languages. Enjoy!

You can find Michele on Twitter at https://twitter.com/mjwhansen/. Also, check out her book Deploy Empathy.

Here is a short summary of the topics discussed in this episode:

How do you set boundaries with a podcast? 3:08

How do you judge what you say against what someone else would perceive as useful for themselves? 9:23

How do you make sure you serve the right customers? 13:06

Focus on what you already have instead of where you can go. 19:47

Work in progress vs. goals. 23:13

The journey is the interesting part, not the destination. 28:54

The challenge of self-actualization after a big transition. 31:58

What was the sign that it was time to go full-time? 39:14

The financial hurdle of being an entrepreneur in the US. 42:35

Where the fear of losing everything comes from. 48:09

The mean voice in your head speaking. 51:43

Being able to recognize your own growth is a big part of entrepreneurship. 57:38

Low expectations allow you to surprise yourself, which leads to a better result. 1:00:47

This episode is sponsored by MicroAcquire. 

Here's the blog post for this episode.
You can also watch this episode as a video on YouTube.