Dave Hersh, former entrepreneur and founder of Jive Software, shares his insightful journey from bootstrapping to IPO and beyond.

Dave is also the Author of 1 in 10,000, a newsletter on The Future of Competitive Advantage: Case Studies and Strategies for Building Moats in the Age of Commoditized Technology

In this episode, Host Alex Shartsis dives into the unspoken challenges of startup growth with Dave, highlighting the pitfalls of premature scaling, the importance of understanding your company's soul, and the often-overlooked impact of a founder's mental health on business success.

Tune in as Dave discusses:

The systemic flaws in the venture capital model and how to navigate them

Strategies for identifying and capitalizing on your company's unique strengths

The critical distinction between ego-driven and soul-driven decision-making

Practical advice for founders on sustainable growth, funding, and leadership development

Gain valuable perspectives from Dave's experiences and apply them to your own entrepreneurial journey.

Show Notes:

0:00 | Introduction

01:12 | From Bootstrapped to Public: Dave's Journey with Jive Software

12:08 | Restructuring for Success: Leadership Lessons from a Turnaround

14:00 | The CEO's Hidden Struggle: Mental Health, Wellness, and Company Performance

20:02 | The Waste in Venture Capital: Why Premature Scaling Often Fails

28:50 | Investors vs. Customers: The Conflict That Can Sink Your Business

41:47 | The Human Advantage: Investing in Emotional Market Openings and Flourishing

45:25 | From Ego to Empathy: Jesse's Transformation and the Power of Culture Shift

53:04 | Transforming Yourself, Transforming Your Company: The CEO's Intuitive Journey

Guest: Dave Hersh(linkedin.com/in/davehersh)

Host: Alex Shartsis (linkedin.com/in/shartsis)

Audio Engineer & Video Editor - James Fixx (fixxmusic.com)

Music by the Great White Shark (Shark Shartsis)

The Seed to Sequoia podcast is created by Silverwood Advisors to help founders with practical advice on building successful startups.

If you would like to get expert advice for your startup reach out to us on:

Website: silverwood.ai

Linkedin: linkedin.com/company/silverwood-advisors

Tony Stubblebine is the CEO of Medium, a renowned platform for writers and readers, and a seasoned entrepreneur with a rich history in tech, having co-founded several successful startups.

Join Alex Shartsis in this episode as Tony shares his personal anecdotes and hard-won insights from turning around Medium, highlighting the importance of situational leadership, and navigating the challenges of scaling a platform. He also reflects on his earlier experiences, including the rise and fall of Odeo, and the unexpected success of Twitter, providing a nuanced understanding of the entrepreneurial journey.

This episodes will give you actionable advice on how to adapt your leadership style to drive growth, and develop a deeper understanding of the intricacies involved in scaling a successful platform.

Show Notes:

0:00 Introduction

1:16 Tony Stubblebine's Background and Introduction

2:07 Evan Williams' Impact on Online Publishing

20:09 Pivotal Decisions in Medium's Growth

36:41 Medium's Turnaround to Profitability

48:38 Overcoming Financial Challenges at Medium

49:12 Medium's Ambition and Growth Strategy

50:53 Differentiating Medium in the Market

1:06:46 Lessons on Patience and Perseverance in Entrepreneurship

Guest: Tony Stubblebine (linkedin.com/in/tonystubblebine/)

Host: Alex Shartsis (linkedin.com/in/shartsis)

Audio Engineer & Video Editor - James Fixx (fixxmusic.com)

Music by the Great White Shark (Shark Shartsis)

The Seed to Sequoia podcast is created by Silverwood Advisors to help founders with practical advice on building successful startups.

If you would like to get expert advice for your startup reach out to us on:

Website: silverwood.ai

Linkedin: linkedin.com/company/silverwood-advisors

Luke Hohmann is a serial entrepreneur, author, and pricing expert. He recently wrote "Profit Streams," a book about effective software pricing strategies. With experience in multiple startups, successful exits, and even a significant failure, Luke brings valuable insights to the table.

Join Host Alex Shartsis in this episode as Luke shares crucial knowledge about software pricing strategies, challenging common misconceptions and highlighting the risks of underpricing in the tech sector. They discuss the benefits of bootstrapping, the importance of understanding customer value, and how to avoid common pricing errors as companies grow. Luke also provides practical advice for founders on quantifying value, institutionalizing customer feedback, and making smart hiring decisions.

Show Notes:

0:00 Introduction

1:04 Luke's background

2:58 The importance of pricing in software companies

11:15 Benefits of bootstrapping and equity retention

22:30 Case study: Underpricing in AI fraud detection

36:51 Common pricing errors as companies grow

49:10 Understanding reference pricing

59:28 The importance of discount analysis

1:17:06 Best practices for founders

Guest: Luke Hohman (linkedin.com/in/lukehohmann/)

Host: Alex Shartsis (linkedin.com/in/shartsis)

Audio Engineer & Video Editor - James Fixx (fixxmusic.com)

Music by the Great White Shark (Shark Shartsis)

The Seed to Sequoia podcast is created by Silverwood Advisors to help founders with practical advice on building successful startups.

If you would like to get expert advice for your startup reach out to us on:

Website: silverwood.ai

Linkedin: linkedin.com/company/silverwood-advisors