"Imposter syndrome isn’t just a moment of self-doubt — it’s all-encompassing. It prevents founders from taking action, from taking a risk in the first place." This week, Dr. Julie Gurner shares with me how high performers combat the challenges founders commonly face. She’s a performance coach and Doctor of Psychology. We’ll talk about dealing with imposter syndrome, burnout, how to deal with the avalanche of advice on Twitter, and why it is so hard for founders to cope with stress. The blog post...
Jun 14, 2023•58 min•Transcript available on Metacast Sharing your journey as an entrepreneur can be scary, but it's a great way to connect with your audience and demonstrate your expertise. Let's explore the difference between sharing business insights and trade secrets, and construct a Share/Don't Share list to help you decide what to share with your audience. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm The blog post: https://thebootstrappedfounder.com/how-to-build-in-public-without-revealing-too-much/ The podcast epis...
Jun 09, 2023•16 min•Transcript available on Metacast Joe Masilotti is the founder of RailsDev —a reverse job board— and a Turbo Native consultant. In this conversation, we explore Joe Masilotti's philosophy on entrepreneurship and his focus on empowering software developers to find work. Joe's approach to monetizing Open Source is particularly interesting: he gives away his product for free with an eventual revenue share. We delve into the various marketing strategies that Joe uses for his different business ventures, including cold emailing, cont...
Jun 07, 2023•59 min•Transcript available on Metacast If you're an entrepreneur looking to start a digital business, you might be tempted to aim for a "forever business" right from the start. However, pursuing this approach can be dangerous. Today, you'll learn how to navigate the rapidly evolving landscape of digital entrepreneurship, build successful businesses that serve your customers and owners, and avoid the pitfalls of pursuing a "forever business" from day one. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm The blog...
Jun 02, 2023•11 min•Transcript available on Metacast In this episode, I interviewSimon Høiberg, an active software engineer, founder, and YouTuber. Simon shares his strategies for balancing his roles as a creator and maker, and discusses the importance of incorporating personal experience into his content. He also delves into the power of intrinsic motivation and joy in entrepreneurship, and how he gamifies his life to prioritize these elements. The conversation touches on topics such as productivity, mental health, team management, and burnout pr...
May 31, 2023•57 min•Transcript available on Metacast Have you ever searched for the perfect resume to get hired? Or tried to create a product that appeals to everyone? This essay explores the logical fallacy of wishful reasoning and the importance of picking a niche. Discover why building a successful product means addressing a specific set of needs for a particular group of customers, and why a well-defined niche is the best place to start. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm The blog post: https://thebootstrap...
May 26, 2023•8 min•Transcript available on Metacast Evelyn J. Starr is a brand-building expert. We talk about finding the right niche, having a community-centric long-term perspective, and how brands evolve —you might call it “grow up”— over time. Here’s Evelyn. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm Evelyn's Twitter: https://twitter.com/EvelynJStarr The blog post: https://thebootstrappedfounder.com/evelyn-j-starr-the-evolution-of-a-brand/ The podcast episode: https://share.transistor.fm/s/69cc34f4 The video: http...
May 24, 2023•50 min•Transcript available on Metacast Building in public is a popular trend in entrepreneurship. However, it may not always be the best approach. Entrepreneurs should consider their personality traits, the nature of their business, and their competitive advantages before deciding whether to adopt this approach. Building in public is about generosity, transparency, and community, and can be a powerful way to gain customers' trust, build a brand, and grow a business if these values align with the business model and personal style — bu...
May 19, 2023•12 min•Transcript available on Metacast Today, I’m talking to Jack Ellis, the co-founder of Fathom Analytics, a privacy-conscious web analytics business that I personally use for all my web properties. The company that Jack co-founded with Paul Jarvis competes directly with Google on their linchpin advertising product. That’s a pretty high order. We chat about Jack's role in a growing successful software business and just how much he hesitates to go from coder to manager. We dive into choosing reliable dependencies to power an always-...
May 17, 2023•54 min•Transcript available on Metacast People would rather sift through fake AI results than see yet another ad. Something is happening in advertising, and the creator economy is affected greatly. The shift towards trust-based advertising is a wake-up call for founders and creators when crafting their marketing strategy, as honesty, integrity, and trust are now essential components of a successful approach to outreach. Here are the steps that you need to take to keep up with this development. My new podcast project: Arvid & Tyler...
May 12, 2023•12 min•Transcript available on Metacast When Fatih started his sticker business Stikkernet, his peers asked him, “You’re a developer; why don’t you write this from scratch?” His response? “Why should I?” Today, I'm talking to my dear old friend Fatih Kadir Akın — or fka for short. We discuss his unexpected journey of building a successful business out of a simple idea. Fatih shares his experience with building Stikkernet and how he grew his audience through community building. We chat about the challenges of logistics when shipping in...
May 09, 2023•54 min•Transcript available on Metacast What happens when we encounter something so novel that our minds can't fully comprehend it? Today, let’s explore the "Rubber Band Effect" and how it impacts both journalists and entrepreneurs alike. Learn how to build products that fit seamlessly into your customers' workflows and how to effectively communicate the results your product can achieve, without overwhelming them with the complexity of the underlying technology. The Ai researcher's video "The A.I. Dilemma": https://www.youtube.com/wat...
May 05, 2023•8 min•Transcript available on Metacast “As an entrepreneur, you need someone you’ve been through shit with already” — and that’s exactly why Dagobert and Lucie are the perfect power couple co-founders. I chatted with @dagobertrenouf about overcoming struggle, growing a business together, and dealing with the lack of motivation when things get complicated. We discuss the power of Twitter and building an audience before creating a product. Dagobert shares his personal journey with Logology and how he lost motivation before finding insp...
May 03, 2023•1 hr 2 min•Transcript available on Metacast Using ChatGPT as a writing partner helps strengthen arguments by acting as an editor, proofreader, and devil's advocate. It prompts the AI to provide counterpoints and can detect emotional subtext, highlight missing pieces of the argument, and suggest better examples. This adversarial writing approach with generative AI results in writing that is both in the author's voice and accessible to a wider readership. 00:00:14 Intro 00:01:33 ChatGPT as a writing buddy 00:03:13 Bias-busting with a Devil'...
Apr 28, 2023•10 min•Transcript available on Metacast Few people had an impact on my founder journey as Dr. Sherry Walling — and she didn't even know. But I got to tell her! We discussed burnout, imposter syndrome, and stress among founders. Sherry explained the need for mental health professionals who understand the unique challenges of entrepreneurship and shared that burnout is a diagnosable issue. While entrepreneurs have more control over their work, long hours and hustle culture can still lead to burnout. Her book, "The Entrepreneur's Guide t...
Apr 26, 2023•55 min•Transcript available on Metacast This week, I got on my first post-COVID trip and headed to Denver, Colorado for MicroConf 2023. It. Was. Awesome. Unsurprisingly, being in the same room with 250 other bootstrapped SaaS founders is one of the nerdiest things you can do. And it was as enlightening as it was nerdy. I just arrived back home in Canada a few hours ago, so I took the opportunity to share my insights from the conference on my podcast. Enjoy! 00:00:14 Intro 00:02:26 What is MicroConf? 00:08:42 STIR 00:11:21 The talks 00...
Apr 21, 2023•49 min•Transcript available on Metacast When it comes to building an "owned audience," nothing beats an email list. Louis Nicholls is a newsletter expert, and he shared with me how to monetize a list, how to grow it reliably, and why cold emails are often done spectacularly wrong. Louis will show you how to do email right. 00:00:00 Why did you choose to build SparkLoop? 00:05:23 Grow an audience, monetize a list 00:09:07 How do you maintain customer quality in a network? 00:14:55 Advice on how to cross-link your knowledge with other c...
Apr 19, 2023•51 min•Transcript available on Metacast ChatGPT is everywhere. But can we build businesses on it? What risks will we face? Let's dive into the future of entrepreneurship in a world where AI is ubiquitous. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm The blog post: https://thebootstrappedfounder.com/chatgpt-goldmine-or-minefield-for-indie-hackers/ The podcast episode: https://share.transistor.fm/s/efd69983 The video: https://youtu.be/J4eNi1uqxUI You'll find my weekly article on my blog: https://thebootstrappe...
Apr 14, 2023•20 min•Transcript available on Metacast Marie and Ben are a power couple. Together, they run Notion Mastery, an intense workshop for people who want to use Notion professionally and productively. In our conversation, we'll dive into platform risk, building a sustainable educational business, how to work together as a couple, and why social media distribution matters a lot to educational founders. Enjoy! 00:00:00 What can we learn from permaculture? 00:04:55 How do you make it profitable? 00:10:57 Building an info product on top of a s...
Apr 12, 2023•1 hr 5 min•Transcript available on Metacast Artificial scarcity, a marketing tactic that fosters urgency in customers, can lead to short-term financial gains but raises ethical concerns and negative consequences in the creator economy. Drawbacks include damaging relationships, promoting impulsive purchases, and exacerbating global inequality. While there are exceptions, such as outcome-oriented communities and front-loading financial gains, adopting an abundance mindset and cultivating genuine relationships is a more sustainable long-term...
Apr 07, 2023•15 min•Transcript available on Metacast Most of Josh Spector's newsletter issues are just a few sentences. Sometimes, just a link. And still, advertisers and readers alike flock to Josh's emails. In our conversation, you will learn why brevity is so attractive, how to make sure you're telling the right stories to the right people, and how to build systems that keep people coming back for more. 00:00:00 How to think about scarcity 00:04:16 Josh's newsletter(s) 00:08:49 Ads that feel less like ads 00:12:21 Why you need to know what you ...
Apr 05, 2023•1 hr•Transcript available on Metacast This is probably the most concentrated and well-produced podcast I've been on in a long while. And I want to share it with you here today as a bonus episode. Kudos to @YongSooChung for putting his money where his mic is. He spent a lot of time, money, and energy to make this episode happen. This is a great ep, and if want to learn about my whole founder journey, I recommend a listen. Here's the original show: https://www.firstclassfounders.com/life-changing-wisdom-with-arvid-kahl-from-selling-a-...
Apr 03, 2023•36 min•Transcript available on Metacast What are the factors involved in choosing a solid business name? From securing an available domain to choosing a unique name for SEO reasons, I delve into the linguistic and cultural considerations of choosing a business name, including avoiding potentially offensive or negative connotations in various markets. I also emphasize the importance of trademarking the business name and domain to protect from infringement and legal disputes. Future-proofing a business name involves securing social medi...
Mar 31, 2023•17 min•Transcript available on Metacast Peter knows how to get good domains and turn them into businesses. He's selling onions, helps dude ranchers get clients, and will share his approach to monetizing domains as well as purchasing them on the cheap side. Peter's been building online marketplaces for a while, and he'll teach you how he approaches setting up profitable businesses. 00:00:00 Peter’s unique approach to building a business. 00:02:59 The right mindset to become an entrepreneur. 00:05:46 Getting into domain name investing. ...
Mar 29, 2023•1 hr 4 min•Transcript available on Metacast Here are my personal strategies for achieving consistency in content creation, which encompass implementing accountability systems, connecting with my audience, and reaping financial and lifestyle rewards. Additionally, I explore the difficulties of maintaining motivation and the vital role of community in this process. I recount my own story, beginning with the launch of a blog and ultimately leading to the development of a self-perpetuating content creation cycle. Throughout this journey, I've...
Mar 24, 2023•20 min•Transcript available on Metacast Justin Jackson has been successfully bootstrapping Transistor.fm with a small team throughout the ups and downs of a shifting economy. He even rejected massive clients to be able to keep running a calm and self-funded business. Find out just how important it is to stay independent, resilient, and nimble, and what building on open standards has to do with that. 00:00:00 Justin Jackson 00:01:24 The world of ideas 00:10:32 Understanding the context of advice. 00:15:58 The importance of attribution ...
Mar 22, 2023•1 hr 6 min•Transcript available on Metacast Looking to build a successful SaaS business? Don't just focus on product-market fit. In this video, learn about the Solution-Workflow Fit, a crucial element to consider for success. Discover why the medium in which your solution is implemented and the workflow of your customers matter just as much as the technical side of your solution. See real-life examples and learn how to research your target industry's existing workflows, design your solution to fit between existing tools, and adapt your so...
Mar 19, 2023•12 min•Transcript available on Metacast Rob Fitzpatrick is a serial entrepreneur, a writer, a community leader, and a very curious human being. I talk to Rob about building an incredibly complicated business, the world of self-publishing, what AI tools can and will do for humanity, and how to build communities that can run by themselves. 00:00:00 Rob Fitzpatrick 00:03:38 The challenges of building the Useful Books business 00:10:01 A rare breed 00:14:47 The passion discount 00:21:12 What’s changed in self-publishing? 00:26:43 What’s y...
Mar 15, 2023•1 hr 5 min•Transcript available on Metacast How to secure your product, the business, and an eventual exit, including using established frameworks, outsourcing to secure third-party vendors, and having clear and complete account separation. The blog post: https://thebootstrappedfounder.com/securing-your-saas/ The podcast episode: https://share.transistor.fm/s/6c645953 The video: https://www.youtube.com/watch?v=jNOr7BheIz8 You'll find my weekly article on my blog: https://thebootstrappedfounder.com Podcast: https://thebootstrappedfounder.c...
Mar 10, 2023•22 min•Transcript available on Metacast Troy Hunt (of HaveIBeenPwned fame) is a cybersecurity expert who has been around long enough to be able to give actionable and pragmatic security advice without complicating things. In our conversation, we chat about best practices for securing your SaaS business, how to get your family to be more secure, what it means to vet your vendors, if you should build your own authentication and why passwords just won't die. After this conversation, you will know how to adequately secure your SaaS busine...
Mar 08, 2023•53 min•Transcript available on Metacast 
