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The Bootstrapped Founder

The Bootstrapped Founder

Author: Arvid Kahl

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Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.
187 Episodes
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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 Laura's journey00:01:10 The parable of the monkey and the pedestal.00:02:28 A cultural problem00:03:36 Reflecting on the monkey- The Monkey and the Pedestal- 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 entrepreneurshipIf you're interested in Descript, go and check it out here.You can also watch this episode as a video on YouTube.
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 Elizabeth00:02:10 Running a non-technical founder podcast00:09:28 Hiring the right people00:12:14 Hiring people who can do something you can't00:17:27 Being able to do everything is both awesome and frightening 00:20:13 Experimenting with different modes of delegating00:25:45 Establishing an internal process for your business00:30:00 On Phrasing00:36:30 The importance of having a mentor00:42:04 Providing the fertile ground for luck to strike00:45:04 The hardest part is overcoming your inner demon00:52:56 Why it's good to have an expert for website personalization00:56:33 Where you can follow Laura- Building Software Products As a Non-Technical Founder With Laura Elizabeth- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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.- Expanding Your Opportunity Surface- 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 entrepreneurshipIf you're interested in Descript, go and check it out here.You can also watch this episode as a video on YouTube.
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 Fayle00:05:35 Getting started with Chekkit00:09:00 Local marketing & picking verticals00:12:05 When to hire a team?00:17:25 Integrations00:22:33 Pricing choices00:25:32 How to be inspired by competition?00:29:54 The importance of customer support00:36:31 Setting limits on free trials00:41:55 Use the tech that your customers use00:47:15 How to stay on top of your game- Door-to-door to $2M ARR with Daniel Fayle- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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-honored tradition of butt-in-seat-hands-on-keyboard that so many managers consider to be the pinnacle of productivity.Remote work does away with this.00:00:00 Remote Work is Here to Stay00:01:28 Async is the New Default00:04:42 The Deep Work Zone00:06:17 Trust and Having Nowhere to Hide- The Role of Trust in Remote Work - 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 entrepreneurshipYou can also watch this episode as a video on YouTube.
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 Workplaces00:02:03 What is Remote Work Prep?00:06:54 The right approach to go about remote work.00:11:00 Traditional hiring doesn’t work for remote teams.00:17:29 Integrating rest into your work.00:23:10 The perversion of productivity & responsiveness policies.00:27:27 Issues with video calls.00:31:02 The difference between a conversation and a phone call.00:37:12 How to transition from pandemic remote to normal remote.00:41:10 The culture of control and top-down decision-making.00:45:29 There’s no place to hide with remote work.00:51:58 How do you keep doing what you do?00:56:23 What is impostor syndrome? What is it and why does it exist?- Running a Remote-First Business with Marissa Goldberg- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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 the more founders I talk to, whatever stage of their journey they might be on, I hear them tell me the same story too. Whether they just started out or sold their business for millions a few years ago, they still struggle with who they are, what they should be doing, and proving themselves and their worth to others.00:00:00 Intro00:00:29 Sponsor00:01:44 Introduction00:02:50 Balancing Parenting & Business00:04:58 Overthinking00:06:22 Addictions00:08:03 Dealing with Failure00:09:45 Not delegating can lead to anxiety00:11:13 Burnout & Dreading Loss00:12:49 Navigating imposter syndrome when others appear successful00:14:44 Second-guessing decisions and dealing with incomplete data00:16:29 Underestimating and Judging Yourself00:18:14 Debilitating Shiny Object Syndrome 00:19:54 Feeling guilty for taking a break00:21:09 Underwhelming Sales00:24:03 Outro- Founder Mental Health Pitfalls- 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 entrepreneurshipThis episode is sponsored by Senja.You can also watch this episode as a video on YouTube.
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 Introduction00:01:04 Patrick's entrepreneurial journey00:03:10 A different approach to marketing00:06:23 Help Sells: providing free value and then selling00:13:53 Dealing with a $200mil exit00:15:55 Filming a documentary while exiting00:19:03 Keeping the company running during the sale00:24:42 Anxiety during the sale00:28:08 Anxiety AFTER the sale00:34:12 Jumping right back into work00:37:28 Building trust with your team00:41:49 Defining your role in a deal00:45:05 Will Patrick ever take a vacation?00:49:38 It never ends: mental health for founders00:54:05 The future of the payment industry- Life After a $200mil Exit with Patrick Campbell- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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 content for different formats. Additionally, it is important to collaborate with other creators, use social media to drive traffic to your own platform, and focus on building a community rather than just an audience. Finally, it is essential to regularly back up your work and data in order to protect yourself from being de-platformed.- Diversify Your Creator Portfolio- 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 entrepreneurshipThis episode is sponsored by MicroAcquire.You can also watch this episode as a video on YouTube.
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 there00:05:00 A trust-based paradigm for your work00:12:15 The importance of being a human being and not a brand00:18:11 Challenges of aligning all of your projects under one umbrella.00:23:02 Can you even find good names at the start?00:28:57 The importance of having a backlog of ideas.00:32:37 Will I ever get to this level of quality?00:37:05 Choosing priorities00:43:11 The mechanics of building community & building relationships with people00:46:15 Teaching sentient beings to do things that are good for them (and good for you)00:50:42 An audience is like an insurance policy- Creative Commitments with Jay Clouse- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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 conversations. Setting specific goals for the amount of sharing you want to do each week or month can help you stay on track.- Realistic Building in Public for Introverted Founders- 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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 about being introverted, working with introverts, and serving introverts. Here’s Ana.00:00:00 Entrepreneurship and Introversion00:10:13 Growing up being introverted without knowing what it is00:16:57 A History of Introversion00:22:49 The loud and shouty approach to social media00:27:33 How do you stay quiet when you’re selling?00:34:07 You’re the magnet for signals from the people around you00:42:45 How to do self-promotion as an introvert vs. an extrovert00:49:03 You attract what you put out, not what you sayThis episode is sponsored by MicroAcquire. Here's the blog post for this episode.You can also watch this episode as a video on YouTube.
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.Today, I am talking to Sahil, the CEO of Gumroad, about what prompted this change, what happened to cause such a stir, and where Gumroad is heading in the future. Here’s Sahil.You can find this conversation on YouTube.
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 when they feel pressure to sell a business that’s not very stable or profitable in the first place.Being able to show that potential competitors have to climb a rather sizeable barrier to entry into your market will net you a significant premium when it’s valuation time. The absence of such a moat around your entrepreneurial castle will push down the price you can ask for. While buyers will still acquire profitable businesses without an oversized advantage, it’s a good idea to consider how you can set up a moat around your business. It will make things much easier.- Build a Defensible 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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 a lot of it with us today.00:00:00 Introduction00:00:54 Founder and personality00:04:19 MicroAcquire: the first venture00:09:51 On being relatable00:13:42 From B2B to Human2Humman00:20:10 What was missing in the market?00:27:07 What makes a business more sellable?00:32:14 Tips for selling your business00:39:07 Working in the business vs. working on the business00:46:47 You can’t succeed without failure00:52:59 Any exit, no matter how small, is a good stepThis episode is sponsored by MicroAcquire. Here's the blog post for this episode.You can also watch this episode as a video on YouTube.
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 entrepreneurshipThis 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 entrepreneurshipThis 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 entrepreneurshipThis episode is sponsored by MicroAcquire. You can also watch this episode as a video on YouTube.
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Comments (1)

ID23617468

Good episode! Take accountability on the issue.

Oct 13th
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