Jack Leeney is a Co-Founder and Managing Partner at 7GC, a venture capital firm with a unique cross-border approach that bridges the innovation ecosystems of the US and Europe.

Before founding 7GC, Jack was at the forefront of some of the most iconic tech IPOs of our time during his tenure at Morgan Stanley, including Tesla, LinkedIn, and Facebook.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

7GC website - https://7gc.co

Jack Leeney on LinkedIn - https://www.linkedin.com/in/jack-leeney

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode, we talk about -

- 7GC's Unique Investment Philosophy

- How and when should US Startups think about expanding into Europe

- Evaluating Growth-Stage Companies and Valuations

- The Transition from Startup to Scale-up CEO

- Leveraging AI in Portfolio Companies and Venture Capital

& lots more

Timestamps:

(00:00) Introduction

(02:46) Jack's background and career journey before co-founding 7GC

(03:02) Inspiration behind founding 7GC and their unique investment philosophy

(07:13) Discussion on when and how US startups should expand into European markets

(15:25) Regulatory challenges and considerations for expanding into Europe, using Hims as an example

(18:12) Strategies for targeting specific European markets

(19:19) Key factors 7GC looks for when investing in growth-stage companies

(25:15) Discussion on valuation multiples and investment approach

(32:05) Advice for founders seeking growth-stage funding

(38:06) Challenges of transitioning from startup CEO to scale-up CEO

(43:30) Use of AI in 7GC's portfolio and within the venture capital industry

(49:04) Rapid-fire round with quick questions about 7GC's investment strategy

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Dominique Levin is a 2x CEO, a go-to-market architect, and a wildly successful investor with over a billion dollars in exits. She’s seen it all, and she has a playbook for a lot of challenges founders face while building their companies.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Links-

Dominique Levin on LinkedIn - https://www.linkedin.com/in/dominiquelevin

Book that Dominique Levin:

1. Survival to Thrival: She mentioned this is a two-book series written by Bob Tinker and Tae Hea Nahm.

* Book 1: Survival to Thrival: Building the Enterprise Startup (The Company Journey)

* Book 2: Survival to Thrival: Change or Be Changed (The People Journey)

2. The Machine That Changed the World: The Story of Lean Production by James P. Womack, Daniel T. Jones, and Daniel Roos.

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode, we talk about -

- Why founders should sell before they build

- The "SAFER" Note: A radical new funding model for founders who want to avoid the VC treadmill.

- The secret behind her success as a VC with over $1 Billion in exits

- Why the future isn't about work-life balance, but building a company that lets your team lead multiple lives

- Remote work, how should leaders think about it, and how it promotes inclusivity

& lots more

Timestamps:

(00:00) Introduction

(02:38) First discussion on go-to-market strategy

(02:57) Common mistakes founders make in go-to-market strategy

- Worrying about go-to-market too soon

- Having multiple go-to-market motions

- Mismatch between go-to-market motion and product/contract value

(05:33) Definition of product-market fit

- Solving a "hair-on-fire" problem

- Validating by selling before building

- Customers willing to pay for a solution

(07:18) Approaching product development

- Think big but act small

- Solve a specialized, unaddressed problem

- Be 10X or infinitely better than existing solutions

(08:53) Fundraising advice for early-stage founders

- Focus on customers first

- Have at least three paying customers

- Traction is the most important thing for investors

(10:26) Building repeatable and scalable revenue processes

- Treat sales as a process or "revenue factory"

- Align marketing, sales, and customer success

- Use AI to optimize go-to-market motion

(13:11) AI applications in go-to-market strategies

- SEO/LLM content creation

- Lead generation

- Prospecting research

- Sales engineering support

(15:57) Investing approach and philosophy

- Looking for unfair competitive advantage

- Leveraging unique relationships and information

(19:15) Balancing product development with sales and customer success

- Sell first, build later

- Minimum effort to prove solving a critical problem

(20:15) Building high-performance teams

- Outward mindset- Focus on customer impact

- Clear mission and vision

(23:10) Transitioning from startup to scale-up

- Different leadership styles at different stages

- Adapting to company growth

(25:31) AI and automation in SaaS

- Becoming AI-native

- Potential for customer-funded businesses

- Alternative funding models

(27:42) One-and-done funding model- SAFE-R (Simple Agreement for Future Equity with Repayment)

- Aligning investor and founder interests

(30:40) Building and managing remote companies

- Challenges of hybrid work

- Importance of in-person interactions

- Maintaining team productivity

(37:31) Flexibility in remote work

- Project-based roles

- Portfolio careers

- Accommodating personal life and work

(43:00) Work-life balance and parental leave

- Personal experiences with parental leave

- Challenges for working parents

(47:35) Rapid-fire round about investing

- Sectors, stages, and investment approach

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Itamar Novick is a solo capitalist and the founder of Recursive Ventures, a pre-seed & seed fund focused on fintech, AI and emerging tech startups. Itamar has been on all sides of the startup table: as a founder and executive, an institutional VC, and an angel investor. He has supported over 50 successful startups, including Deel, HoneyBook, Placer, Credible among others.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Itamar Novick on LinkedIn - https://www.linkedin.com/in/itamarnovick

Itamar's blog - https://www.itamarnovick.com/

Recursive Ventures website - https://www.recursiveventures.com/

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode we talk about -

- What does it mean to be a solo-capitalist?

- His learnings from Life360 and Gigya

- How AI is enabling him to 10x himself 

- The one man unicorn made possible with AI

- His biggest learning investing in startups over the years

& lots more

Timestamps:

(00:00) Introduction

(02:22) Itamar's story of becoming a solo capitalist

(04:08) Difference between solo GP and solo capitalist model

(05:07) Story of investing life savings in Life360

(07:28) Initial journey at Life360 and role in the company

(09:36) How operational experience shaped investing philosophy

(12:01) Investment decision-making process at pre-seed stage

(14:50) Exciting themes and sectors for investment

(17:12) Thoughts on AI models potentially replacing application layer startups

(20:35) Patterns of startup success and anti-patterns

(23:41) Using AI to enhance VC processes and decision-making

(27:52) Current market perspective - "have and have-nots

(29:58) Approach to valuation and investment in AI startups

(32:01) Investment instruments - SAFEs vs priced rounds

(34:38) Biggest learning from investing in startups - founder grit and determination

(36:47) Rapid fire round begins - sectors and regions of investment

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Sean Byrnes is a co-founder & General Partner at Near Horizon. Sean has spent the past 20 years founding and scaling companies that have defined new categories, including Flurry—the world’s largest mobile analytics platform, acquired by Yahoo—and Outlier.ai, an automated data analysis leader.

At Near Horizon, Sean partners hands-on with founders, combining deep operational expertise and capital to help launch the next generation of AI-powered startups.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Near Horizon website - https://www.nearhorizon.vc/

Breaking Point Newsletter - https://www.breakingpoint.tech/

Sean Byrnes on LinkedIn - https://www.linkedin.com/in/sbyrnes/

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode, we talk about -

- Why Sean thinks venture capital is the most risk averse asset class?

- Why VCs are struggling to return capital to LPs?

- His unique approach to investing at Near Horizon Ventures

- What should founders focus on in the earliest stage of a startup?

- Why founders need to think small to move faster at the early stage

- How can founders be more outcome focused?

& lots more

Timestamps:

(00:00) Introduction

(04:13) Near Horizon's unique investment model of working with solo founders

(08:28) Challenges of innovating in venture capital

(09:15) Perspectives on LP (Limited Partner) resistance to new VC models

(14:06) Discussing liquidity problems in venture capital

(18:25) Strategies for early exits and secondary markets

(22:26) Why venture capital is the most risk-averse asset class

(27:03) Key focus areas when working with early-stage companies

(31:26) Importance of customer research and distribution advantage

(35:41) The concept of "thinking smaller" to grow faster

(38:26) Why status meetings are ineffective

(41:12) How founders can be more outcome-focused

(43:33) Rapid fire round of questions about Near Horizon's investment approach

(46:16) Closing remarks and ways to follow Sean Byrnes

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Collin West is the Founder and Managing Partner of Ensemble VC, a venture capital firm he launched in 2020 to harness data science for discovering and supporting exceptional founding teams. Collin’s investment track record spans industry leaders like Zoom, Carta, Groww, ICON, Tally, and Sidecar Health.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Ensemble VC website - https://www.ensemble.vc/

Collin West on LinkedIn - https://www.linkedin.com/in/collinwest/

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode we talk about -

- How they leverage data & algorithms to find the startups with the best founding teams

- What defines a good founding team for them?

- The secret behind his great track record with multiple unicorn outcomes like Zoom, Carta, Groww among several others

- How AI will change how VCs operate?

- The new AI co-pilot for VCs that they've recently launched

& lots more

Timestamps:

(00:00) Introduction

(01:00) Collin's background and early entrepreneurial journey

(02:59) Story of crossing the Arctic Ocean and lessons learned

(05:11) How Ensemble VC uses data to identify and invest in startup teams

(09:50) Discussion of successful investments like Zoom, Gro, and Carta

(13:23) Addressing potential limitations of data-driven investment approach

(15:19) How Ensemble VC wins access to the best deals

(19:28) Detailed discussion about specific investments, including Zoom

(23:14) Introduction of AI co-pilot for VCs

(25:16) Traits of successful founders and team building

(27:28) Current trends in venture capital and AI

(29:35) How Ensemble VC supports portfolio companies post-investment

(31:31) Biggest learning in startup investing

(33:44) Potential of AI to preserve investment strategies

(35:16) Advice for startup founders

(36:19) Rapid fire round of questions about Ensemble VC's investment strategy

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Adam Breckler is the Co-founder and Head of Product at Better Health. Adam is a seasoned entrepreneur and product expert. At Better Health, he leads efforts to simplify access to medical equipment and support for people with chronic conditions, combining technology, peer coaching, and education to improve patient outcomes.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Better Health website - https://joinbetter.com/

Adam Breckler on X - https://x.com/adambreckler

Adam Breckler on LinkedIn - https://www.linkedin.com/in/adambreckler/

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode we talk about -

- Early idea validation

- Go to market strategy

- Product market fit

- Fundraising & hiring approach

- Capital allocation

- Taking care of mental health as a founder

& lots more

Timestamps:

(00:00) Introduction to the podcast and guest Adam Breckler

(02:12) Adam's background and early entrepreneurial journey

(03:39) Origin of Better Health and initial idea validation

(05:05) Discussing starting a startup with life partner

(06:22) Go-to-market strategy in the early days

(07:11) Fundraising and seed round details

(08:50) Approach to finding and selecting investors

(09:53) Initial hiring strategy and recruiting first employees

(11:21) Recruiting senior talent and competitive hiring

(12:28) Hiring strategy and resource allocation

(14:19) Approach to building and maintaining company culture

(16:22) Onboarding, performance tracking, and managing employee performance

(17:38) Product-market fit journey and challenges

(19:45) Understanding product-market-channel fit

(21:01) Building moats and defensibility in the business

(22:01) Key metrics the company tracks

(23:23) Vulnerable moments as a founder and dealing with startup challenges

(25:26) Managing personal mental health and work-life balance

(27:14) Using a business coach

(28:16) Managing family life while running a startup

(29:18) Lessons learned from previous startup experiences

(31:15) Most pivotal decision that changed the company's growth trajectory

(32:49) Closing remarks and how to learn more about Better Health

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Shikha Rawal is Senior Legal Counsel at Alpha Wave Global. With over eight years of experience in corporate law, Shikha specializes in mergers and acquisitions, corporate governance, and securities law. She provides strategic legal advice and support for Alpha Wave’s global operations and portfolio.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Shikha Rawal on LinkedIn - https://www.linkedin.com/in/shikha-rawal-12934b8b/

Alpha Wave Global website - https://www.alphawaveglobal.com/

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode, we talk about -

- The key clauses in term sheets and shareholder agreements that protect investors' interests, such as preferential liquidation rights and anti-dilution provisions

- How can startups effectively protect their intellectual property during fundraising rounds?

- What regulatory requirements must startups comply with during fundraising, and how can they avoid common pitfalls?

- What are the most common corporate structures for startups, and how do they impact fundraising and investor relations?

- How do founders' agreements prevent conflicts among co-founders, and what should they cover?

- How should founders protect themselves against exploitative clauses in the term sheet? How to check for these, and what are some common ones?

Timestamps:

(00:00) Introduction

(03:15) Guest Shikha Rawal introduces herself and her background

(04:14) Key clauses in term sheets and shareholder agreements that protect investor interests

(07:21) How investors protect against governance issues in startups

(10:41) How startups can effectively protect their intellectual property during fundraising rounds

(13:12) Discussion on best jurisdictions for registering startup companies

(17:04) Regulatory requirements startups must comply with during fundraising

(19:19) How founders' agreements prevent conflicts among co-founders

(21:55) How founders can protect themselves against onerous clauses in term sheets

(25:00) Importance of legal counsel for founders during fundraising

(26:39) Closing remarks and contact information for Shikha Rawal

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Yoni Tuchman is a Partner at DLA Piper representing sponsors and investors in forming, investing in and operating private funds. This episode marks the beginning of a new segment on the podcast called Legal10x where we will be talking about the legal aspects of funds & startups.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

Yoni Tuchman on LinkedIn - https://www.linkedin.com/in/yoni-tuchman-58153b5/

Yoni Tuchman on X - https://x.com/TuchmanYoni

DLA Piper website - https://www.dlapiper.com/en

In this episode, we will talk about:

- Key legal structures commonly used in venture capital fund formation

- What is the diamond structure?

- What is the difference in building a fund versus building a firm?

- Things that first time fund managers get wrong

& lots more

Timestamps:

(00:00) Introduction to the podcast and the Legal 10x segment

(03:43) Guest Yoni Tuchman introduces himself

(04:11) Discussion begins on key legal structures in venture capital fund formation

(04:33) Explanation of fund structure - single limited partnership approach

(08:16) Clarification on what GP (General Partner) means in legal context

(09:33) Benefits of the diamond structure in fund formation

(18:35) Discussion on why venture funds invest in Delaware C Corps

(24:01) Importance of understanding potential investors when forming a fund

(33:00) Difference between building a fund versus building a firm

(45:00) Discussion on Limited Partnership Agreement (LPA) key elements

(51:24) Common pitfalls for first-time fund managers

(54:07) Closing remarks and how to find more information about Yoni Tuchman and DLA Piper

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Anand Rajaraman is a serial entrepreneur and venture capitalist known for co-founding Junglee, which was acquired by Amazon, and Kosmix, acquired by Walmart. He was Senior Vice President at Walmart Global eCommerce and is a founding partner at Rocketship.vc.

Rajaraman is also the co-owner of the San Francisco Unicorns, a Major League Cricket team. Anand has invested early in companies like Facebook and Lyft and focuses on backing high-growth startups globally, but in this episode we will limit our conversation to owning a cricket team and maybe do another episode later to talk about Anand's entrepreneurial & investing success.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

San Francisco Unicorns website - https://www.sfunicorns.com/

Major League Cricket (MLC) website - https://www.majorleaguecricket.com/

Anand Rajaraman on LinkedIn - https://www.linkedin.com/in/anandrajaraman/

In this episode, we talk about -

- Why did he decide to buy a cricket team

- The business angle of owning a sports team

- Key revenue streams for franchise cricket leagues & teams

- Leveraging data & technology in all aspects of team management

- The signing of 2 Australian legends: Pat Cummins as a player, & Shane Watson as the coach

- The emotional toll of owning a sports team

& lots more

Timestamps:

(00:00) Introduction to Anand Rajaraman and the podcast episode

(03:48) Why Anand decided to buy a cricket team in Major League Cricket (MLC)

(05:18) Choosing the San Francisco Unicorns and the reasoning behind the team name

(07:23) Parallels between business world and owning a sports team

(10:59) Applying data and analytics to team management

(13:35) Investment perspective on owning a sports team

(18:26) Revenue streams for cricket leagues and teams

(22:30) Player acquisition and salary cap details

(23:52) Player selection strategy for the team

(27:53) Discussion about Pat Cummins joining the team

(33:11) Hypothetical scenario of Indian players in MLC

(34:17) Emotional aspects of owning a sports team

(40:12) Reflections on the 2024 season and reaching the championship match

(42:43) Growth of cricket in the USA and impact of the 2023 World Cup

(45:23) Long-term vision for team ownership

(46:20) How to follow San Francisco Unicorns and Major League Cricket

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.

Andrew Reilly is a Managing Director at VCFA, the world's first secondary focused fund. Andrew joined VCFA in 2017 primarily to focus on origination and development of venture and growth equity secondary opportunities.

Links:

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

VCFA website - https://vcfa.com/

Andrew Reilly on LinkedIn - https://www.linkedin.com/in/andrew-k-reilly-5782a019/

🎙️ Hosted by Prashant Choubey

Follow Prashant on X - https://x.com/ChoubeySahab

Follow Prashant on LinkedIn - https://www.linkedin.com/in/choubeysahab

In this episode we talk about -

- The history of VCFA and being the first secondary fund

- The different types of secondaries they deal in at VCFA

- How they buy winners at a discount

- The difference between direct secondaries VS GP leds VS LP interests

- How do they evaluate a VC portfolio for a secondary transaction

- Sourcing high quality secondary deals

- What is the risk/return profile of secondaries

& lots more

Timestamps:

(00:00) Introduction

(02:49) History of VCFA and Dayton Carr, founder of the secondary industry

(07:31) Types of secondaries: GP-led transactions, LP-led deals, and direct secondaries

(11:11) Evaluating a VC firm's portfolio for acquisition

(13:34) Why sellers would sell assets at a discount

(35:27) Sourcing high-quality secondary deals

(41:08) Risk-return profile of secondaries

(47:08) Goals for the new fund, including potential expansion into real estate secondaries

(52:28) Rapid fire round of questions about VCFA's investment strategy

For sponsorship or guest appearance requests, write to [email protected]

Subscribe to VC10X on Youtube, Spotify, Apple Podcasts.