The Bootstrapped Founder

Today, I’m talking to Hassan Osman— he’s the host of Writer on the Side, and himself a prolific writer. We talk about crafting books that sell (and keep selling), self-publishing on Amazon, and how to write while having a full-time job. Here’s Hassan! 00:00:00 Introduction to Hassan Osman 00:05:59 Slowly shifting your perspective 00:10:48 Do you update your books that you have written? 00:17:24 Ho...

Arvid talks about how applied kindness builds a brand and an audience. In a hostile world, many founders isolate themselves, but this isn't sustainable. Kindness changes the world, so be honest when self-promoting and set boundaries with hostility. Kindness can be seen in every aspect of life, creating a cycle of positive change. The blog post: https://thebootstrappedfounder.com/be-the-kindest-per...

KP talks about building in public, sharing your journey, and becoming a respected community member. Today, I’m talking to KP — the build-in-public guy. KP has been a pillar of the indie hacker community, and we talk about how to involve yourself, empower others, and eventually build a community around your personal brand and the things you care about. Here’s KP. 00:00:00 KP’s founder hotline 00:04...

Negative reviews are an important part of the customer experience, as they provide valuable feedback to creators about how their product or service is being perceived. Reviews can be a source of frustration for founders, as they may not reflect the quality of the work, but rather the disconnect between the customer's expectation and the reality of the product. It is important for creators to stay...

Brennan shares the secrets to using emails to build relationships and increase your revenue. Today, I’m talking to Brennan Dunn, the founder of Palladio, co-founder of RightMessage, and general email expert. As a newsletter author myself, I took to this opportunity to learn as much as possible about personalizing and optimizing my email strategy. You’ll also hear what most people get wrong in emai...

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success. 00:00:00...

Today, I’m talking to Laura Elizabeth. She co-hosts the Non-Tech Founders podcast and runs several products as a non-technical founder. We talk about outsourcing, trust, and building an audience around your business. Here’s Laura! 00:00:00 Laura Elizabeth 00:02:10 Running a non-technical founder podcast 00:09:28 Hiring the right people 00:12:14 Hiring people who can do something you can't 00:17:27...

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success. - Expand...

Today, I’m talking to Daniel Fayle — co-founder of Chekkit, a business he and his team have boostrapped to $2mil in ARR. We’ll touch on finding the right vertical to get started, how to do things that don’t scale, and what choices need to be made to get a business to 7 figures.  00:00:00 Daniel Fayle 00:05:35 Getting started with Chekkit 00:09:00 Local marketing & picking verticals 00:12:05 Wh...

I was chatting with Marissa Goldberg about remote work this week , and she gave me several handy frameworks for founders who want to build remote-first businesses. At the center of any successful remote work relationship lies trust. And surprisingly, many businesses have a tough time trusting anyone once they can't see them at their desk in the office. Remote work is throwing a wrench in the time-...

Today, I’m talking to Marissa Goldberg. She’s an expert in remote work and guides companies and founders alike toward a future-proof workplace. We’ll talk about productivity, best practices for going remote, and setting up a remote team of all sizes. Here’s Marissa. 00:00:00 Remote Work and Future Proof Workplaces 00:02:03 What is Remote Work Prep? 00:06:54 The right approach to go about remote wo...

This week I chatted with Patrick Campbell about his exit of ProfitWell to Paddle for $200 million. One of the most mind-blowing things that I experienced during that conversation was hearing Patrick tell me that he feels he needs to build something else to prove that his exit -$200 million- was not just a fluke. I did not expect that, but I should have because I feel the same way all the time. And...

Today, I’m talking to Patrick Campbell, founder of ProfitWell, a bootstrapped business that recently got acquired by Paddle for a whopping 200 million dollars. I talked to Patrick about getting acquired for 9 figures, finding your footing as a founder after such an incredible exit, where the online payment industry is heading, and how mental health challenges follow us wherever we go. 00:00:00 Int...

As a creative entrepreneur, it is important to diversify your portfolio and have multiple projects in progress in order to reach a wider audience, stabilize income streams, and protect yourself from the risks associated with relying on any one platform. In order to do this, it is essential to own the means of communication with your audience, such as through a newsletter or blog, and to repurpose...

Today, I’m talking to Jay Clouse, a creative entrepreneur, and all-around amazing human being. We’re talking about keeping it all together as a solo creator, what makes a personal brand work, and how important authenticity is in building an audience. 00:00:00 What to do about all the attention-grabbing out there 00:05:00 A trust-based paradigm for your work 00:12:15 The importance of being a human...

Sharing your work and process in public can be difficult for introverted entrepreneurs and creators, but it can help build credibility and trust with your audience, gather valuable feedback and insights, and even lead to new opportunities. Tips for sharing in public include reframing why you do it, taking it slow and steady, breaking it into small chunks, scheduling posts, and engaging in conversa...

Today, I’m talking to Ana Bibikova, a defender and cheerleader for introverts in entrepreneurship. Ana knows what it means to be skeptical of loud and salesy marketing tactics. They might work great for extroverts, but not so much for the quiet types. Today, we’ll talk about how you can build a public-facing brand without resorting to all the obnoxious and much-too in-your-face tactics. We’ll talk...

Yesterday, the creator economy learned that Gumroad, a platform where creators have been building their businesses by selling their services and products, increased their prices significantly. That caused a lot of backlash in the community, with people threatening to switch to other platforms and criticizing how the price hike was communicated. It’s been an intense topic of community discussion. T...

When it comes to selling a small indie business, defensibility is a key factor that potential buyers will consider. A unique moat, or competitive advantage, lets your business stands out from the competition and is seen as a valuable acquisition. Many small founders sell their businesses because they want to get rid of them, and that attracts bargain hunters. It’s easy to negotiate a founder down...

Today, I am talking to Andrew Gazdecki, a pillar of the founder community and himself founder of the acquisition platform formerly known as MicroAcquire — but we’ll learn more about that on the show. Besides organizing millions of dollars worth of acquisitions every month, Andrew is a true teacher. His content on building software businesses is spectacularly useful. And fortunately, he will share...

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 depe...

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...

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 un...

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...

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 th...