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High Stakes

Paige Soya
Venture Capital
K Street Capital
Generative AI
Venture Liquidity
Power Law
Angel Investing
Y Combinator
Diversity
Secondaries
Deal Sourcing
Thinknimble
Key Street Capital
BA Venture Fund
Networking
Pre-Seed
Julie Castro Abrams
Women Investors
Valuation
Black Founders
Quorum

Join seasoned investors and successful start-up founders as they weigh in on topics and trends currently dominating the venture capital space. Each episode brings together a founder and an investor to provoke a deepened understanding of the topic at hand. If you want to learn about how early-stage venture capital investing works, this show is for you.

PublishesTwice monthlyEpisodes72Founded3 years ago
Number of ListenersCategories
InvestingBusinessEntrepreneurship

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Artwork for High Stakes

Latest Episodes

What actually creates a competitive moat?

For years, founders believed the answer was simple: build a better product.

Today, venture investors increasingly believe the answer is distribution.

In this episode of High Stakes, Paige Soya and Nick Dua... more

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Not all venture deals are created equal, and understanding the fine print can make a significant difference for founders.

In this episode of High Stakes, K Street Capital's Paige Soya and Nick Duafala are joined by Scott Stern, Partner at Origin Ven... more

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What makes a pre-revenue startup worth investing in?

Before there's revenue, traction, or a long list of customers, venture investors have to make decisions with limited data. So what signals matter most? How do VCs build conviction around a founder... more

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How do venture capital firms actually exit their investments when startups are staying private longer than ever before?

On this episode of High Stakes, hosts Paige Soya and Nick Duafala sat down with Andrew Seter, Principal at Savano Capital, to un... more

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Recent Guests

Scott Stern
Partner at Origin Ventures
Origin Ventures
Episode: How VCs Structure Venture Deals | Paige Soya, Nick Duafala & Scott Stern (Partner, Origin Ventures)
Charles Hudson
Managing partner at Precursor Ventures
Precursor Ventures
Episode: How VCs Evaluate Pre-Revenue Startups | Paige Soya, Nick Duafala & Charles Hudson (Precursor Ventures)
Andrew Seter
Principal, Savano Capital
Savano Capital
Episode: Venture Liquidity, Secondaries & How VCs Exit | Paige Soya, Nick Duafala & Andrew (Principal at Savano Capital)
Matt Bressler
Co‑founding GP of Lookout Ventures (formerly at TDF Ventures)
Lookout Ventures
Episode: VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)
Haley Bryant
Partner at Hustle Fund, co-chair of Black VC and the DMV
Hustle Fund
Episode: Power Dynamics in VC | Paige Soya, Nick Duafala, Haley Bryant (Hustle Fund), & Ann Marie Guzzi (Dalmatian Ops, Angel Investor & Agora Initiative)
Ann Marie Guzzi
Entrepreneur and Angel Investor at K Street, founder of The Agora Initiative
Dalmatian Ops, Agora Initiative
Episode: Power Dynamics in VC | Paige Soya, Nick Duafala, Haley Bryant (Hustle Fund), & Ann Marie Guzzi (Dalmatian Ops, Angel Investor & Agora Initiative)
Neil Shah
CEO and founder of ThinkNimble, angel investor with Key Street Capital
ThinkNimble; Key Street Capital
Episode: How VCs Evaluate Founding Teams | Paige Soya, Nick Duafala, & Neil Shah (CEO, ThinkNimble)
Dadi Akhavan
Angel investor, longtime partner at K Street Capital
K Street Capital
Episode: Angel Investors vs. VCs | Paige Soya & Dadi Akhavan (Startup-to-IPO Founder)
Taylor Margot
Partner at Lytical Ventures
Lytical Ventures
Episode: How VCs Source Deals | Paige Soya, Nick Duafala & Taylor Margot (Partner, Lytical Ventures)

Host

Paige Soya
Host of High Stakes; Managing Partner at K Street Capital

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#53
Argentina/Business/Investing
Apple Podcasts
#230
Argentina/Business
Apple Podcasts
#232
India/Business/Investing

Talking Points

Recent interactions between the hosts and their guests.

VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)
Q: What is the biggest bottleneck that slows deals down?
Negotiating and finalizing the term sheet and related legal documents is the primary bottleneck, often slowed by back-and-forth between lawyers and coordinating multiple parties.
VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)
Q: What accelerates deals the fastest when you're evaluating early-stage opportunities?
Deep knowledge of the space, a strong thesis, prior familiarity with the founder, and upfront access to required data and references that verify claims speed up diligence and shorten the window to a term sheet.
Not All Capital Is Created Equal: Venture Capital vs. Other Funding | Paige Soya & Jill Ralph (Former Chemonics Capital and Motley Fool)
Q: What's a practical way for new investors to get started in venture?
The guests suggest joining a organization or syndicate to pool resources and access smaller checks, and to use AI tools to assess venture-backability before reaching out to potential VCs.
Not All Capital Is Created Equal: Venture Capital vs. Other Funding | Paige Soya & Jill Ralph (Former Chemonics Capital and Motley Fool)
Q: Who should really be considering venture capital as a funding option?
Jill emphasizes that venture is best for founders building in non-profitable, high-growth spaces with scalable business models, while other founders may be better off bootstrapping or using debt.
Not All Capital Is Created Equal: Venture Capital vs. Other Funding | Paige Soya & Jill Ralph (Former Chemonics Capital and Motley Fool)
Q: What are the asset classes most people should consider before venturing into VC?
Paige explains that while stocks, bonds, and real estate are common, venture capital sits at the high-risk end of private investments and should be approached with clear conviction and an understanding of long timelines.

Audience Metrics

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Frequently Asked Questions About High Stakes

What is High Stakes about and what kind of topics does it cover?

This show gathers seasoned investors and startup founders to unpack core dynamics in early-stage venture funding, with a frequent focus on how AI and technology trends reshape team building, diligence, and funding strategies. Episodes typically pair a founder-facing investor with an operator or investor guest to surface practical signals, deal mechanics, and governance insights that founders and fund managers can apply in real-time. Notable traits include a clear bias toward actionable diligence frameworks, founder psychology, and the economics of ownership, often anchored in real-world anecdotes from the DC and broader tech ecosystem. Listeners who want sharper fundraising instincts, better founder-investor fit, or practical VC playbooks w... more

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High Stakes launched 3 years ago and published 72 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on High Stakes?

Recent guests on High Stakes include:

1. Scott Stern
2. Charles Hudson
3. Andrew Seter
4. Matt Bressler
5. Haley Bryant
6. Ann Marie Guzzi
7. Neil Shah
8. Dadi Akhavan

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