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Startup Success - Highlights from the Past 6 Months of Our Podcast Series

As our special 100th episode approaches in September, we look back at inspiring stories and insights from the first half of 2024.

Burkland’s Startup Success podcast launched at the beginning of 2021 with a vision to share the stories behind the successes at some of today’s most innovative companies. Since then, I’ve had the pleasure and privilege of interviewing dozens of startup founders, investors, and service providers who are shaping the future of business. Along the way we’ve explored the unique and sometimes surprising challenges behind scaling a successful startup, and the inspiring and creative ways entrepreneurs have risen to meet these challenges. We’ve heard amazing stories from founders who have generously shared their hard-won wisdom with us, and insights from VCs who offered us special inside looks at how they operate and make investment decisions.

This September, we’ll be celebrating a special milestone for the podcast series with our 100th episode. Stay tuned for our special guest, to be announced soon!

In this article, we’ll revisit a few especially compelling discussions from the past six months.

An Inside Look at How a Venture Capital Firm Operates

Earlier this month I sat down with Josh Gilbert, CFO of the VC firm Freestyle. Among other topics, Josh discussed the heightened importance of due diligence in today’s venture capital landscape compared to several years ago. For startup founders looking to raise capital, this means being well-prepared to withstand rigorous scrutiny. Josh advises founders to ensure their pitches are backed by solid business models, clear growth strategies, and demonstrable traction, as VCs now, more than ever, need to carefully vet potential investments to discern genuinely viable opportunities from the multitude. For early-stage founders, understanding this shift towards more comprehensive due diligence can be key to successfully navigating the fundraising process.

Listen to my discussion with Josh Gilbert and browse Burkland’s due diligence articles.

Legal 101 for Startups

We recently took a dive into the world of legal strategy for startups with Charu Satia, startup attorney and Partner at Silicon Legal Strategy. A big picture takeaway from my discussion with Charu is that startup founders often tend to wait too long to engage professional legal counsel. Charu emphasized that betting on your success means laying a strong legal foundation from the start, and this approach can save time, money, and headaches down the road. In particular, she spoke about the importance of addressing such issues as entity formation, founder equity, IP protection, corporate governance, and tax and securities filings early in a company’s development. Like my discussion with Josh at Freestyle, my talk with Charu also touched on the importance of being prepared for investor due diligence. If legal issues are found during due diligence, it can erode investor confidence and complicate the funding or acquisition process.

Read more highlights from my discussion with Charu Satia, and listen to the full episode here.

Making Founder Mental Health & Well-Being a Priority

This episode explores crucial aspects of founder well-being in the startup ecosystem. Lisa Mikkelsen from Flourish Ventures discusses the need for venture capital firms to support founders beyond financial investment, emphasizing the importance of mental health. The conversation provides practical tips on fostering empathy and identifying signs of burnout, while also addressing the power dynamics between investors and founders. This episode is essential for both startup founders and venture capitalists aiming to cultivate healthier, more sustainable founder-investor relationships.

Listen to my full discussion with Flourish Ventures’ Lisa Mikkelsen.

Startup Wind Downs: How to Come Out on Top

This candid conversation with Andrew Kitirattragarn of Sherwood Partners offers key insights into the critical yet often overlooked topic of managing a startup’s closure effectively. The episode emphasizes the importance of advance planning even when a startup is not facing immediate financial difficulties. It explores the emotional and technical challenges of winding down a venture, such as managing investor expectations and navigating preferred share complexities. Andrew shares his personal journey through his snack food business’s explosive growth and subsequent plateau, which ultimately led to the decision to wind down. The episode is valuable for both startup founders and venture capitalists as it not only explores the strategic steps necessary for an orderly wind-down but also addresses the psychological impacts on founders during this phase.

Listen to my full conversation with Andrew Kitirattragarn about startup wind downs.

A VC’s Optimistic Outlook on Today’s Startup Landscape

My discussion with ff Venture Capital partner John Frankel offered a fresh dose of optimism for the startup sector. Despite the economic downcycle of the past couple years and the inherent risks of early-stage startups, John’s outlook is upbeat, driven by transformative potential and evolutionary advancements in technology like AI, FinTech, drones, and robotics. He emphasized the importance of strategic engagement over mere financial investment, advising early-stage founders to seek venture capital that offers more than capital—highlighting the value of VCs who actively engage, lead funding rounds, and provide strategic guidance. For founders looking to raise venture capital, John underscores the importance of having a balanced team with deep domain knowledge and a clear, defensible business model that leverages secular growth trends, regardless of economic conditions. His advice is valuable for startups aiming to navigate the complex venture landscape and secure funding that will drive significant growth and innovation.

Listen to my full discussion with ff Venture Capital’s John Frankel.

The stories we’ve revisited today are just a small slice of the wealth of knowledge shared through Burkland’s Startup Success series. They underscore the resilience, innovation, and spirit of collaboration that drive the startup ecosystem. Looking forward, we remain committed to bringing you even more insightful and inspiring content. Stay tuned for what promises to be a momentous 100th episode and beyond, as we continue to explore the narratives that will shape the future of entrepreneurship. Whether you’re a seasoned founder, a curious investor, or a newcomer to the startup scene, there’s always something to learn and someone to inspire you at Startup Success. Thank you to all of our guests who share their valuable time and insights, and our listeners who make it all worthwhile.