Seed to Sequoia

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

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

Gregoire Viasnoff is the VP of the Incubation practice of SE Ventures which is a corporate arm of Schneider Electric having 1B+ Assets under management focused on sustainability, energy management and Industry 4.0. Gregoire and his team are transforming ideas into scalable and independent VC backed start-ups. They incubate around 2 companies per year and their young portfolio already includes 1 unicorn: Verkor, 3 exits (EiQ to NextEra, Aplines and Dash Energy to Schneider Electric) and 5 promising seed ventures.

Join Host Alex Shartsis in this episode as Gregoire shares insights into how SE Ventures supports startups from ideation to later stages, emphasizing their ability to provide funding, expertise, and commercial agreements tailored to each company's needs. They talk about the value of deep market insights in shaping successful products, the importance of quality over quantity, timing, and founder motivation in selecting and nurturing startups for success. Gregoire also shares his best practices for founders aiming to build scalable and global companies.

Show Notes:

0:00 Introduction

1:05 Gregoire's journey to corporate VC

7:01 Schneider Electric's presence in energy management

8:58 SE Ventures' approach to accelerating startups

10:34 SE Ventures' support from ideation to later stages

14:35 Investment motivation and decision-making at SE Ventures

25:33 Success story: Verkor and gigafactory investment

27:56 Creating ventures through incubation

49:17 Best practices for founders: Curiosity, team building, and global mindsetGuest: Gregoire Viasnoff (linkedin.com/in/viasnoff/)

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

Nate Williams is the Co-Founder and Managing Partner of Union Labs - an applied DeepTech seed fund focused on building and backing leading seed-stage startups in Climate, PropTech and Mobility. 

Nate is a hands-on serial entrepreneur having previously played roles as an EIR at Kleiner Perkins, CRO & Head of Business at August Home, Inc. which became a leader in Smart Home Access, later acquired by Assa Abloy in 2017. He was also the CMO & Head of Business at Greenwave Systems and Senior Director of Marketing & Business Development at Google subsidiary Motorola Mobility.

Join Host Alex Shartsis in this episode as Nate shares about the different stages of sales in a startup's life, from day zero to a scalable product, and the importance of a team approach to sales efforts.

He shares his advice on creating a channel map to reach customers and markets, and talks about the risks of customer concentration. This channel mapping approach brought huge success when he was heading the business at August Home.

Nate also talks about the significance of the Chief Revenue Officer (CRO) title and the shift in funding trends towards mitigating technical and go-to-market risks early on.

Show Notes:

0:00 Introduction

9:38 Startup Sales Stages: From Jungle to Highway

11:17 Team Approach to Sales: Beyond Founder-Led Selling

15:23 Channel Mapping: Strategic Market Reach

21:11 Early Client Engagement: Setting the Deal Clock

23:38 Customer Concentration Risks: Balancing Goals

35:13 Targeting Influential Profiles: Building Key Relationships

40:23 CRO Role: Signaling Structured Sales Growth

49:52 Funding Trends: Balancing Technical and Market Risks

Guest: Nate Williams (linkedin.com/in/nathandwilliams)

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

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

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

Rob Christenson is the CEO and Co-Founder of oPRO AI, an AI startup that uses machine learning techniques to enable complex manufacturing operations to achieve higher optima — higher yields, lower energy use, reduced emissions, safer and stabilized operations.

Rob has had success in founding companies, going from $0 to one exit at about $100 million a year. He was the SVP of PROS, a leading AI pricing company that he worked on for 14 Years, taking it public.

Join host Alex Shartsis in this episode as Rob shares the journey of Opro AI, from its origins in the oil and gas industry to becoming a leader in industrial automation. He discusses Opro's playbook for tailoring AI solutions to specific industrial needs, emphasizing scalability and consistency. Rob also talks about the importance of strategic planning, building credibility, and ensuring value for customers in the rapidly evolving field of Industrial AI.

Show Notes:

0:00 Introduction

4:22 Origin of Opro AI

8:19 Opro's Industrial AI Playbook

10:49 Expanding Customer Base

12:35 Fundraising for Team Growth

18:45 Scaling Value in Large Markets

22:44 Organizational Growth Strategies

25:42 Indicators for Industry Focus

31:01 Selling Large-Scale Projects

36:56 Evolution of Pilot Programs

47:10 Opro's Vision: AI for Efficiency

Guest: Rob Christenson (linkedin.com/in/rob-christenson-009a463)

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

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

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

Lars Leckie is the managing director and partner of Aspenwood Ventures. He and his partner Steve started their career at the first ever software focused venture capital firm that started back in the late eighties, and took over that firm turning it ino Aspenwood Ventures.

They look for disruptive technologies and market shifts, aiming for companies to reach $100 million in revenue and stressing the importance of building real businesses and identifying founders with a track record of success.

The investing history Lars draws on includes multi billion dollar exits like Hyperion, Omniture, Mulesoft, and five nine.

Join Host Alex Shartsis in this episode as Lars shares with us the significance of sequential focus on product development, sales, and scaling, in that right order and how founder bets in these areas can lead to massive wins for startups.Show Notes:1:57 Aspenwood Ventures' Focus on Enterprise Software

4:12 Early Investments in Founders: Hyperion, Omniture, Mulesoft

8:53 Criteria for Early-Stage Investments: Disruption and Potential

14:14 Mulesoft's Journey: From Startup to Billion-Dollar Acquisition

17:30 Timing the Pivot: Proof Points over Rebuilding

21:10 Capital Efficiency: High Margins Fuel Enterprise Growth

33:57 Founder Priorities: Product, Sales, Then Massive Scaling

37:27 Fundraising Evolution: Adapting Pitches for Each Stage

Guest: Lars Leckie (www.linkedin.com/in/larsleckie/)

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

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

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

Companies Aspenwood Ventures has invested in:

Aria Systems  Sonatype Klue Amberdata ArkoseLabs InsideSales Influitive Alpharank 

Aspire Clarify Health Closefactor Connect The Dots Kloudfuse Klue MobileForce Nfinite Oomnitza Screenmeet Smartaccess Sonatype Stepfunction Symbium Vendia Wundergraph

Lars is also an active angel investor in companies like Tonal, BetterPlaceForests, Masterclass, Uberflip and others.

Chase Woolard is the founder of Early Stage HQ. He is a Bay-Area based talent leader with 12 years of experience helping startups hire and retain great people. The last 8 of those years he has been building and managing high-growth recruiting teams, starting originally in the agency world before moving into working internally, driving talent at venture-backed startups like Perfect Price, AngelList, and Hone.

Join Host Alex Shartsis as Chase underscores lean, smart hiring strategies, the importance of discussing metrics, past performance with potential hires, how job tenure/stability impacts decisions and so much more. Tune in to this episode and learn how to avoid making expensive hiring mistakes.

Show Notes:

3:50 Leaner and smarter hiring strategies advised by VC advisors

8:57 Necessity of hiring a sales-driving individual contributor at the seed stage

10:23 Importance of discussing specific metrics and past performance with potential hires

12:31 Importance of effective hires to avoid wasting money

12:44 Significance of stability, success, and job tenure in hiring decisions

24:37 Distinguishing between sales and marketing roles based on core skill sets and external factors

37:55 Importance of thoughtful offboarding to avoid brand damage and hiring challenges

49:00 Building a hiring brand to attract top talent and avoid negative reviews

Guest: Chase Woolard(linkedin.com/in/cwoolard/)

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

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

Theme music - Matthew “Shark” Shartsis @thegreatwhiteshark

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

This episode explores one of the most underrated and overlooked superpowers for founders and entrepreneurs - the ability to listen deeply to your customers.

It's easy to drift into building products and services based on our own assumptions and hunches. The founders and industry leaders joining us have battle-tested strategies for doing the opposite - obsessing over authentic customer voices to uncover game-changing insights.

You'll learn from Sean Byrnes why a perpetual "learner's mindset" and adaptability are crucial, especially in rapidly evolving tech landscapes. He'll share how your startup's survival may hinge on truly listening to customers.

Janel Galucci takes it a step further with a case study on how she used the voice of the customer to radically reshape her entire marketing strategy and messaging.

Matthew Leibowitz hammers home why a CEO's willingness (or unwillingness) to empathize with customers can make or break an entire venture. He'll share the framework he uses to merge customer listening with industry foresight.

Whether you're an upstart in a garage or a grizzled veteran, this is a master class in stealing an unfair competitive advantage by giving customers the attention they need. World-class founders make it a habit - click play and learn the secrets.

Show Notes:

0:59 Embracing a Learner's Mindset as a Founder in Tech

2:32 Avoid the "Solution Looking for a Problem" Trap

3:59 Using Customer Feedback to Shape Marketing Strategies

4:35 The Power of Authentic Customer Listening

6:35 The CEO's Role in Merging Customer & Industry Insights

8:11 Active Listening: From Interviews to Company Culture

Guests in this episode:

Sean Byrnes (linkedin.com/in/sbyrnes/)

Janel Galucci (linkedin.com/in/janelgallucci)

Josh Posamentier (linkedin.com/in/posamentier/)

Matthew Leibowitz (linkedin.com/in/matthewleibowitz/)

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

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

Theme music - Matthew “Shark” Shartsis @thegreatwhiteshark

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

Matthew Leibowitz is the Co-Founder and Managing General Partner at Plaza Ventures, a growth-stage bespoke venture capital firm that focuses on structuring deals tailored to individual circumstances and strong relationships with companies. He has been a VC his entire professional career spanning 17 years and has seen the ecosystem evolve and completely change over the past 2 decades.

Join Host Alex Shartsis in this episode as Matthew shares with us his observations of what core values set apart the best CEO’s and founders from the mediocre, what are best practices for aligning the board with management teams and other lessons from his long experience as a VC.

Show Notes:

2:54 Unconventional Venture Capital Entry & Pattern Recognition

8:13 Bespoke Fund Structure & Strong Company Relationships

9:34 Providing Liquidity & Lifecyle Investment

16:38 Speed in Deal Execution & Recent 10-Day Transaction

17:53 CEO Best Practices: Overcommunication & Transparency

24:15 Integrity, Honesty, and Growth Mindset

26:17 Customer-Centric Approaches for Business Success

43:52 Prioritizing Customer Empathy for Business Success

47:06 Aligning Investor-Management Interests through Milestone Communication

Guest: Matthew Leibowitz (linkedin.com/in/matthewleibowitz)

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

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

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
Companies Plaza Ventures has invested in:

Kitchen Hub Portless Vivecrop Super Symend Avidbots Hydrostor Kerv Placeholder Site 20/20 Clear Key Iguazio Landr Dejero Hubba CareGuide Drop PostBeyond SweetIQ Q4 Miovision MMBNetworks FindSpace