INDIE AUDIO

Charles Broskoski, co-founder of Are.na, discusses the importance of human-centered online interactions over rapid growth. He shares insights from Are.na's 13-year journey, emphasizing community over algorithms. Charles advocates for creative entrepreneurs to focus on genuine passion rather than trends, highlighting the value of early user feedback. He critiques traditional social media's efficiency-driven models, urging a return to individual discovery and connection, and reflects on crowdfunding as a path to independence in the creative economy.

After wrapping this week’s conversation with published author and ReadySet’s CEO, Y-vonne Hutchinson, I stepped out of the studio, opened my phone, and X was ablaze. In the year of our Lord 2024, a startup had decided that an anti-woke marketing campaign was the best possible way for them to generate attention for their payroll software company. The culmination of this campaign was one of their sales affiliates posting a racist rant. The fallout from this was all over my timeline.  Even the most anti-woke of the tech set found themselves embarrassed and deeply uncomfortable with the direction and velocity the pendulum was swinging. Tech has a tortured relationship with DEI, race, and gender. The world is becoming increasingly diverse, yet the number of employees and funded startup founders from diverse backgrounds has remain unchanged, if not shrunk. Because the Me Too, George Floyd, and Black Lives Matter movements have left a bad taste in the mouths of many tech leaders, I fear we’re at risk of throwing the baby out with the bath water. At the heart of this uncomfortable conversation is something deeply important to company cultures specifically, and the future of tech broadly, so I invited my friend Y-vonne to talk about it. Y-vonne and her company ReadySet were part of the Indie v4 batch of companies. I have a deep respect for her, her work, and the company she’s building. A few takeaways from this conversation:Historical Context of DEI EffortsProgress in diversity, equity and inclusion (DEI) often follows a pattern of advancement followed by backlash and retrenchment. This has happened repeatedly throughout U.S. history. The recent pushback against DEI initiatives can be seen as part of this historical pattern, rather than an isolated event. DEI efforts sometimes focused too much on individual change rather than systemic issues, leading to fatigue.DEI in the Tech IndustryThe broad, nebulous nature of “DEI” as a concept allowed it to become a target for criticism. Some DEI initiatives were performative rather than substantive, causing disillusionment. The tech industry initially embraced DEI efforts, but economic pressures and changing market conditions led many companies to cut DEI programs and staff. Some tech leaders have used DEI as a “boogeyman” to justify cuts, even though the underlying issues of bias and lack of diversity remain unaddressed.DEI as a Business ImperativeY-Vonne argues that DEI should be seen as a tool to solve real business problems like attrition, market share, and product-market fit. Companies that ignore diversity issues risk building products that don’t serve increasingly diverse markets and user bases. Companies should aim for “healthy culture” that enables collaboration and innovation, rather than trying to mandate diversity, but the healthiest cultures are diverse.Moving ForwardWork environments should avoid causing trauma, but shouldn’t be expected to heal past traumas - that’s not their purpose. While companies shouldn’t be responsible for “healing” employees, leaders can adopt a more trauma-informed approach to avoid causing additional harm. Broader social and political change is needed to address systemic issues, beyond what individual companies can accomplish.The world, and its demographics, are shifting so quickly it would be a huge miss for companies not to be thinking about how their culture can reflect the broader universe or potential customers and users. This isn’t about quotas or raising or lowering bars, it’s about capturing opportunity. This was such an engaging and energizing conversation for both Y-conne and I. We hope you enjoy listening as much as we enjoyed recording it.

Steve Schlafman, a former junior investing partner known for his influence in the NYC startup scene, shares his insights on navigating career transitions. He reflects on his journey from venture capitalism to coaching, driven by a desire for authentic relationships. Schlafman discusses the significance of slowing down, embracing self-discovery, and fostering meaningful connections as individuals pivot in their careers. He also introduces Downshift, a 'decelerator' program designed to help high achievers take inventory before embarking on their next chapters.

Angelica Nwandu, the founder of The Shade Room, shares her journey in digital media and impactful storytelling. She discusses the unique challenges faced by Black female founders, emphasizing the importance of mentorship and community support. The conversation highlights the need for ownership in Black media and how Shade Room stands out in a competitive landscape. Angelica reflects on her entrepreneurial path, the significance of authentic audience engagement, and the power of collaboration in fostering cultural relevance.

In a deep dive with Karri Saarinen, cofounder of Linear, they discuss their unconventional approach to building a company with emphasis on quality over rapid scaling. Karri shares insights on maintaining a net-negative lifetime burn rate while raising funds and navigating ‘Founder Mode’ challenges. They also explore innovative hiring practices from Airbnb and Coinbase, and even dive into the delicious world of Finnish potatoes versus American varieties. This conversation is a refreshing take on entrepreneurship that prioritizes craftsmanship and sustainable growth.

Chris and Brendan, co-founders of Wistia, discuss their journey of creating a sustainable lifestyle business. They emphasize the importance of patience and long-term thinking over venture capital dependency. Their experience with a company buyback fostered a culture of ownership and profit-sharing among employees. They advocate for a focus on solving significant market problems while balancing creativity and profitability. The duo highlights that meaningful growth takes time and that building strong workplace relationships is key to success.

The conversation kicks off with an analysis of shifts in the funding landscape, urging venture capitalists to embrace diverse strategies. Exceptional founders who dare to deviate from the norm are celebrated for their unique visions. Insight into the need for support systems reveals how personal aspects, like family, can enhance productivity. Themes of storytelling and emotional journeys in startups highlight overlooked narratives and the importance of genuine fulfillment, while balancing the intricacies of love and business is explored.

Product-market fit requires both customers willing to pay and stay. It’s not just about initial sales, but also retention. Early-stage sales should focus on research and understanding customer problems rather than immediate revenue generation. Founders often skip this crucial research phase.Abstract solutions require focusing on specific problems rather than leading with the technology itself. To create urgency, you need to demonstrate how a problem is growing or intensifying for the customer. If a problem isn’t being measured or managed, it’s likely not a priority.Early adopters are often those early in their buying journey who are willing to experiment. They buy into the founder as a subject matter expert rather than expecting a fully-built product. Successful startups often start by focusing on a specific niche before expanding horizontally. Being highly specialized allows you to understand customer problems better than they do.Invalidation is a healthy part of the startup process. If you’re not invalidating assumptions, you’re likely not learning or going deep enough. Sales feedback is valuable for positioning and refinement, but product vision should come from founders or product leads. Salespeople should not drive product vision. Demonstrating expertise by setting boundaries on what your product does (and doesn’t do) can actually increase customer confidence.

— Capital has no insightsEric argues that venture capital alone doesn’t solve business problems, and having more capital doesn’t necessarily lead to better outcomes.— Compounding value vs. negative valueThe importance of building companies that compound positive value over time, rather than scaling prematurely and compounding negative value. Funding should primarily be used for experimentation and scaling proven business models, not for scaling unproven ideas, because it’s easy to compound negative value if you’re not paying attention to the right things.— Vanity metrics vs. intrinsic valueThe industry often focuses on vanity metrics like growth rates and valuations, rather than building long-term intrinsic value and durable businesses. The venture capital industry’s incentive structures often encourage behavior that may not be in the best interest of building sustainable businesses. It’s important to maintain a long-term perspective on building value, rather than getting caught up in short-term growth or fundraising cycles. In many tech businesses, there are often diseconomies of scale rather than economies of scale as companies grow.— Playing the game on your own termsCEOs and founders are ultimately responsible for making disciplined decisions about resource allocation and scaling. While entrepreneurs can’t completely ignore the “game” of venture capital, they should focus on building value on their own terms rather than getting caught up in comparisons or unrealistic expectations.

Some takeaways:— There’s a significant gap between the hype around AI and its actual implementation in businesses. Many companies are still in the experimental phase, with few AI solutions in production. The main barriers to AI adoptions are technical challenges, cost considerations, and lack of expertise. We’re still very early in realizing AI’s promise.— AI adoption was slow, then immediate. In a pre-ChatGPT world, the focus was on convincing companies to care about data science and machine learning. Post-ChatGPT, there’s been an explosion in demand, with companies actively seeking AI solutions.— Most companies are still in the proof-of-concept stage. There’re limited production-ready AI use cases, which hinders adoption. But with major cloud providers (Microsoft, Amazon, Google) aggressively pursuing AI strategies, that’s bound to change. There’s constant evolution in model performance and capabilities. Companies need to view AI as a continuous investment, similar to cloud infrastructure, rather than a one-time project.— Tribe’s approach to AI implementation is what made it such an interesting investment for indie. Their focus on education to help companies understand AI's potential, and emphasis on quick, cost-effective proof of concepts to demonstrate value, means they’re positioned to continue rapidly growing. As a services business, they’re able to help companies balance cost with value creation, navigate rapidly evolving AI technologies, and future-proofing AI investments.