Startups For the Rest of Us

In this discussion, Tracy Osborn, a bootstrapper expert, and Einar Vollset, a key figure in the bootstrapper arena, dive into the latest happenings in the tech world. They dissect the closure of Indie.vc and what it means for aspiring entrepreneurs. The conversation also touches on the new features from Twitter, including Spaces and Super Follows, and LinkedIn's entrance into the gig economy with its new marketplace. Plus, they explore Shopify's business model changes and compare Google Cloud with AWS onboarding experiences.

Dan Norris, an accomplished author and entrepreneur, shares his journey from selling his service WP Curve to GoDaddy to running a successful brewery in Australia. He discusses the challenges and motivations behind writing six books, particularly his latest, 'Compound Marketing.' Norris reflects on the emotional complexities of life post-exit, touching on themes of financial freedom and the evolving definition of success. The conversation also explores how marketing principles can uniquely apply to the craft beer industry, emphasizing community engagement.

Einar Vollset, an expert in product management and business strategy, joins the discussion to dive into key startup dilemmas. They tackle when to sunset a product and the intricacies of managing multiple offerings. Einar shares insights on navigating enterprise security assessments and highlights the complexities of acquiring businesses with lifetime deals. The conversation also emphasizes the value of authenticity in sales and highlights strategies for startups facing compliance challenges.

Rand Fishkin, a serial SaaS founder known for his work at Moz and now leading SparkToro, shares his candid insights into the startup world. He reflects on the impact of his book, "Lost and Founder," and discusses the transition from Moz to SparkToro. The conversation also touches on the differences between venture capital and angel investing, along with effective growth strategies in today's market. Rand emphasizes the importance of owning your audience channel, making meaningful connections, and adapting marketing tactics for success.

Reflecting on the lessons learned from a tumultuous 2020, Rob shares insights on maintaining perspective during tough times. He discusses the unique opportunities that arise in crises, emphasizing the power of community resilience and hope. The conversation turns to the rise of remote work and creative skills, highlighting how adaptability can lead to innovation. Rob also explores strategies for entering competitive markets and the importance of connecting with an audience to drive success in the future.

In this engaging conversation, Mike Taber, who is actively involved with Bluetick, shares insights from his recent endeavors. He discusses an exciting CRM partnership for field sales reps and the complexities caused by pandemic-related delays. Mike also dives into software product comparisons and redesign efforts, revealing the challenges he faces managing Bluetick alongside a full-time job. The talk doesn’t shy away from the intriguing potential of freemium models and an AppSumo deal, all while navigating the intricacies of Google security audits.

Josh Pigford, the entrepreneur behind Baremetrics, recently sold the company for $4 million after a seven-year journey. He discusses the strategic use of Qualified Small Business Stock (QSBS) to minimize taxes upon sale. Josh shares his emotional decision to sell and the dramatic life changes afterward. He also reflects on raising profitability just months after the sale and highlights his new venture, Laser Tweets, which emerged from a hobby into a successful business.

In this discussion, Adii Pienaar, a seasoned entrepreneur with multiple successful exits, shares insights on 'life profitability,' a concept he emphasizes as vital for measuring success beyond financial gain. He challenges the traditional notion of work-life balance, highlighting its limitations. Adii also reflects on his motivations for writing about personal fulfillment in entrepreneurship and his experiences starting a new venture, Kogzi, while navigating the demanding SaaS landscape. His journey emphasizes the intertwining of personal values and business success.

John Warrillow, an acclaimed author with extensive experience in building and selling companies, shares invaluable insights on the intricacies of selling a business. He discusses the optimal timing for a sale and gaining leverage during negotiations. John introduces the 5/20 rule, explaining common acquirer profiles, and emphasizes the importance of hiring experts to streamline the sell-side process. He explores the emotional hurdles founders face and advises on preparing for a successful exit, featuring anecdotes that resonate deeply with aspiring entrepreneurs.

Colin Gray, founder of The Podcast Host and Alitu, shares his journey from podcast hobbyist to SaaS entrepreneur. He discusses the challenges and triumphs of launching multiple businesses and the key transition to software development. Colin reflects on adapting to competition, navigating the growing podcast market, and balancing creative passion with business strategy. He candidly talks about the struggles of scaling during uncertain times and the importance of audience understanding in building a successful subscription model.