While both play critical roles in the startup ecosystem, the way they invest and what they need from their investments iis fundamentally different.

We explore how those differences shape everything from deal selection to decision-making to founder outcomes.

Key themes include:

• Why venture capital funds are structurally driven to pursue “outlier” returns
• How fund size, LP expectations, and mandates influence VC behavior
• Why angel investors have more flexibility in what and when they invest
• How early-stage founders should think about which type of capital to raise — and when
• The tradeoffs between taking institutional money vs. staying in the angel ecosystem
• What “stage of company” really means in practice for fundraising strategy
• How experienced investors evaluate opportunity differently based on structure, not just preference

Dadi also shares insights from his own journey, from building companies to taking one from startup all the way to IPO, and how that experience shapes his approach to investing today.

This episode is a deep dive into the mechanics behind startup funding decisions, and what founders often overlook when choosing between angels and VCs.

In this episode of High Stakes, K Street Capital Managing Partner Paige Soya sits down with investor Jill Ralph (Motley Fool’s former President of Global Membership, and former VP of Chemonics Capital) to break down Venture Capital 101, from both the investor and founder perspective.

They unpack what venture capital actually is, how it fits into the broader investing landscape, and why it operates so differently from traditional asset classes like public equities. From risk and liquidity to diversification and portfolio strategy, this conversation covers the fundamentals every new investor should understand before entering the space.

But this episode isn’t just for investors. For founders, Paige and Jill dive into a critical question: Is your company even a fit for venture capital? They explore what types of businesses are best suited for VC, what taking on venture funding really means for your company’s future, and how it can fundamentally shape your growth trajectory.

They also cover:

• Why venture capital is considered one of the highest-risk asset classes
• What diversification looks like in a venture portfolio
• How long it typically takes to see returns
• What it means to be an accredited investor and how much capital you need to get started
• How venture-backed companies differ from traditional businesses

Whether you’re an aspiring investor looking to break into venture or a founder evaluating funding options, this episode provides a clear, foundational understanding of the risks, rewards, and realities of venture capital.

Because while venture is high risk and long-term, it also offers something unique: the opportunity to back innovation early and watch it grow from the ground up.

In Venture Capital 101, K Street Capital Managing Partner Paige Soya and Principal Nick Duafala break down how venture capital actually works for founders, investors, and anyone curious about the startup ecosystem.

In this opening episode, Paige and Nick share the origin story of K Street Capital and their own paths into venture, from Wall Street and investment banking to founding and exiting a fintech company.

They discuss:

• How K Street Capital started as an angel syndicate and evolved into a venture platform
• Why early-stage investing is different from traditional finance
• What makes venture capital unique compared to other asset classes
• How investors evaluate startups and work alongside founders

Along the way, they also talk about some of the companies K Street has backed, from digital health platforms to AI-powered robotics, and what makes those opportunities exciting.

This episode sets the stage for the rest of the season, where Paige and Nick will walk through the full venture capital playbook, including angel investing vs. VC, startup evaluation, deal terms, portfolio strategy, and more.

If you're a founder thinking about raising capital, an investor interested in venture, or just curious about how the startup funding world works, this season is designed to be your starting point.

Listen to the full episode and follow along as we break down Venture Capital 101.

Just over a decade ago, there were only 12 women-run funds. Today, there are more than 380. We are in a watershed moment—one filled with opportunity, friction, and long-overdue change. Julie breaks down not just why this moment is happening, but what’s still holding women back from fully participating in the ecosystem.

Together, Paige and Julie uncover the lived experiences, expertise, and decision-making strengths that women bring to venture—and the systemic obstacles that still stand in their way, from misaligned financial advisor incentives to outdated assumptions about risk, time, and wealth.

Whether you’re a GP, an operator thinking about becoming an LP, or simply curious about how capital flows and who gets to shape innovation, this episode is packed with insights you won’t want to miss.

In This Episode, We Cover:

The Real Barriers Keeping Women from Investing

• Why the biggest limitations aren’t ability or interest, but access, time, exposure, and friction
• How financial advisors, often unknowingly, disincentivize clients from exploring alternative investments like VC
• Why the question “Do you personally invest in venture?” can reveal critical advisor blind spots
• How inherited wealth, fear, lack of exposure, and over-reliance on traditional systems impact women differently

YC’s Bookface allows founders to rate their experiences with investors — creating a private reputation system that influences who founders choose to work with in the future. The result? A new era where investor behavior, transparency, and credibility matter just as much as capital.

💡 In this episode:

• How YC’s Bookface works behind the scenes
• What investor ratings mean for fundraising strategy
• Why reputation has become a competitive advantage for VCs and angels
• How this shift is redefining accountability in venture capital

Watch now to learn how your reputation has become your strategy in the evolving world of startup investing.

In this episode of High Stakes, host Paige Soya sits down with Jennifer Neundorfer, Managing Partner at January Ventures, for a candid conversation about the early fundraising decisions that can make or break a startup’s future.

Together, they dig into the nuances of when to raise capital, who to take money from, and how much equity to give away and the ripple effects those choices have on company trajectory, investor fit, and founder control.

From bootstrapping to pre-seed, Jen and Paige share real examples of companies that got these calls right and others that didn’t - plus actionable guidance for founders navigating their first round.

What You’ll Learn:

• When to raise: How to know if you’re truly ready for outside capital and why raising too early can hurt more than help.
• Who to raise from: The dangers of taking the wrong investor money and how to identify the right venture partners for your business.
• How much to raise (and give up): Why founders should aim to give up no more than 25% early on, and how multiple small rounds can quietly cause major dilution.
• Real-world examples: What happens when pre-seed investors impose “weird” terms and how it can stall future fundraising.
• Investor perspective: What makes a company uninvestible from a venture firm’s point of view.

In this episode of High Stakes, Paige Soya sits down with Melissa Bradley, General Partner at BAE Ventures, to challenge that misconception and explore why portfolio diversity can actually fuel stronger returns.

Melissa shares her experience investing across sectors, from tech to CPG, and how diversity isn’t just about representation, it's about building companies that understand different customers, markets, and opportunities.

Watch the full episode for a deeper dive into how diversity drives returns.

In this episode of High Stakes, host Paige Soya sits down with early-stage investor Matt Gittleman to unpack the art and science of diligence. From scorecards and rubrics to founder storytelling and grit, Paige and Matt explore why rigid frameworks can fall short and how experienced investors read between the lines.

You’ll learn:

• Why scorecards and rubrics can be gamed (and what to use instead)
• Matt’s “levers and hurdles” approach to evaluating startups
• How speed, style, and grit signal founder potential
• Why the way a founder articulates their vision can matter more than the metrics
• The limits of AI in a process that’s deeply qualitative and human-driven

Whether you’re a founder preparing to fundraise or an investor refining your own diligence process, this conversation offers a candid look into how early-stage deals really get done.

Henri shares the brutal realities of fund performance, including why only 16% of funds make it to Fund IV and how the 2021 vintage created one of the tightest performance bands in 20 years. But beyond the financial metrics like TVPI and DPI, we explore the operational indicators that successful VCs track daily: graduation rates, win ratios, cash efficiency, and the often-overlooked importance of deal access and founder relationships.

In this episode of High Stakes, host Paige Soya (Managing Partner, K Street Capital) sits down with Nasir Qadree, Founder and Managing Partner of Zeal Capital Partners, to explore what LPs really want from VC fund managers and why it matters.

They cover:

• What LPs look for when deciding whether to re-up with a fund
• Why many institutional investors are leaning into emerging managers
• How individual LPs think about risk, liquidity, and the “long game” of venture
• The difference between being an investor and being a fund manager
• Why strong communication, transparency, and firm-building matter just as much as returns

Nasir also shares lessons from raising Zeal Fund II, the importance of aligning with LPs beyond capital, and why DC is uniquely positioned to create category-defining companies.

If you’ve ever wondered how LP priorities shape the venture ecosystem (and ultimately, what gets funded), this episode offers a candid inside look.

In this episode of High Stakes, Paige sits down with Sean Glass (entrepreneur, investor, and founding partner at Ayuda Partners) to unpack the mechanics of venture capital decision-making. Together, they explore:

• Why venture returns rely on power-law outcomes
• The importance of market size and market dynamics when evaluating startups
• The pitfalls of messy cap tables, notes, and SAFEs and how they can derail a deal

Sean also shares insights from his own entrepreneurial journey, including raising capital in tough markets, achieving outsized returns for early investors, and building conviction around companies that can define entirely new categories.

Whether you’re a founder raising capital, an investor honing your thesis, or just curious about how VCs make high-stakes decisions, this conversation is packed with hard-won lessons from both sides of the table.

What does a $2M check actually mean for the founder, the investor, and the future of the company?

In this episode of High Stakes, Paige Soya sits down with Michael Bosch to unpack the mechanics behind venture capital that most founders and even some investors get wrong. From rigid ownership targets to flexible fund strategies, and from GenAI-fueled capital efficiency to cap table waterfall risks, this conversation gets into the tactical realities behind early-stage funding.

You’ll learn:

• Why check size, ownership percentage, and stage must be aligned
• How generative AI is reshaping team size, round size, and outcomes
• What investors really mean when they say they need 10%
• Why early investors can get wiped out even when a company wins

If you're a founder raising capital or an investor navigating the new VC landscape, this episode breaks down what really matters and what’s changing fast.

In this episode, they cover the real work behind board seats, share war stories from boardrooms and explain why the right board can literally save companies from bankruptcy.

Moving beyond the quarterly meeting stereotype, Paige and Brian dive into the substantial work that happens between board meetings. They discuss how effective board members provide ongoing strategic support, help founders navigate cash flow crises before they become critical, and serve as trusted advisors during the inevitable ups and downs of startup life. The conversation explores the real motivations behind VC board seat requirements, moving beyond simple control narratives. Brian explains how board seats enable better value creation through ongoing visibility and trust-building. He also discusses how they provide necessary governance rights to protect LP interests. They discuss the delicate balance between serving as a fiduciary to the fund while remaining a supportive partner to founders, especially when these interests might appear to conflict.

In this debut episode of High Stakes, Paige Soya, Managing Partner at K Street Capital, sits down with James Barila, Former Revolution VC investor, now Executive Director at Station DC, for a candid conversation about the realities of running a venture fund – beyond sourcing deals.

They unpack the not-so-glamorous core responsibilities of a VC that don’t get the headlines they deserve but keep a firm alive. 

The episode also explores why emerging managers need to be setting up a DC ground game strategy early. For founders in tech and innovation-driven sectors, engaging with the Washington ecosystem is not optional. Proximity, presence, and participation can be the difference between momentum and missed opportunities.

Whether you're an emerging manager, a founder navigating policy, or an LP curious about what happens behind the scenes, this episode offers a clear-eyed look at the unglamorous – but essential – side of venture.

In this episode of High Stakes, Paige Soya (Managing Partner, K Street Capital) sits down with Alex Wirth, CEO & Co-founder of Quorum, to unpack the habits, mindsets, and leadership lessons that helped him scale his company from 2 founders to 300+ employees over 10 years.

Key takeaways:

✅ How to build the right team at every stage of growth

✅ When founders need to evolve their leadership style

✅ The role of mindset and resilience in navigating startup highs & lows

✅ Lessons on scaling without overextending your cash flow

Whether you’re a VC or an operator, this conversation is packed with timeless advice.

You'll Learn in This Episode:

● How Venture Institute is reshaping VC education to cultivate tomorrow’s top investors

● Why deep roots in the startup ecosystem aren't just helpful—they’re your unfair advantage

● Myrto’s bold leap from accelerator programs to deploying capital

● The incredible story of a candidate who coded their way into a VC role

● What sets Venture Institute’s analyst training apart

● The fundraising muscle every fund manager must build

Whether you’re an aspiring investor, curious about breaking into VC, or want to understand how new funds are formed, this episode is packed with real world insights and inspiration.

#startups #venturecapital #careerventurecapitalist #VC #VCLab

• How Dori’s own shutdown journey inspired the creation of SimpleClosure
• Hidden liabilities and risks founders and VCs often miss
• What happens to intellectual property, equity, and employee obligations
• Data from 2023–2024: which startups are shutting down, where, and why
• The surprising prevalence of founder-led shutdowns
• Visa challenges for international founders during closures
• How SimpleClosure streamlines the wind-down process
• The role of VCs in helping founders exit cleanly and move forward

Whether you’re a founder, operator, or investor, this episode is a must-listen for understanding the realities of startup shutdowns—and how to navigate them with integrity.

In this episode of High Stakes, host Paige Soya sits down with Tony Chan, partner at ORIC and seasoned venture capital and M&A expert, to explore the hard truths of venture investing. Tony shares insights into what happens when deals go south—and what investors can (and should) do when startups are struggling.

Key Points From This Episode:

• Common examples of how companies can handle early closures and exits.

• The importance of early, honest conversations when things aren’t going to plan.

• Why founder optimism and investor caution can be hard to reconcile.

• Founder trust in VCs: how it hinges on operating experience and credibility.

• Navigating misaligned incentives among early and late-stage investors.

• What really happens behind the scenes before and after a board meeting.

• How disciplined investors avoid FOMO and spot underfunded opportunities.

• Why some startups are turning to even-sided mergers instead of IPOs.

• The growing role of secondaries in private market liquidity.

• How VC is shifting as private equity becomes more accessible to retail investors.

Key Points From This Episode:

• Mark’s journey from entrepreneurship to venture capitalism.

• Lessons from being an angel investor and limited partner (LP).

• The value of being on the board of companies you’ve invested in.

• Key advantages and challenges of leading investments.

• How to take the size and resources of your VC firm into account.

• The difficulties of following on in oversubscribed rounds.

• Unpacking the necessity of aligning with co-investors.

• Mark’s advice to founders on how to find the right VC fit for your company.

Key Points From This Episode:

• No straight path: a founder’s guide to a career in early-stage venture capital.

• Why empathy and people skills matter more than traditional finance experience.

• The power of networks: how relationships open doors.

• How the best investors assess risk, luck, and opportunity.

• Key traits of successful VCs, including dedication, creativity, and resilience.

• Insight into what it really takes to break into the venture capital world.

• Taking bold, unconventional action to stand out from the crowd.

• The magic of winging it, embracing failure, and just making the leap.

Key Points From This Episode:

• Bruce’s background in government and commerce and his time at SoftBank.
• How American policies compare with regulatory approaches in other countries, like China.
• Challenges SoftBank successfully navigated when working with the US government.
• Predictions for the new administration: potential regulatory changes and their effects.
• How SoftBank helped companies by giving them access to a government affairs team.
• What Bruce considers his biggest failure in the VC industry and what he learned from it.
• Final thoughts from Bruce and the best advice he has ever gotten: “Be nice to everyone.”

Links Mentioned in Today’s Episode:

• Bruce Andrews on LinkedIn
• SoftBank Group
• Gambling Man
• 'Blackstone’s Byron Wien Discusses Lessons Learned in His First 80 Years'
• Stay at Risk and Live Forever: Lessons from a Life of Curiosity, Grit, and Reinvention
• Paige Soya on LinkedIn
• K Street Capital
• K Street Capital on Youtube

Key Points From This Episode:

• Focusing on things you can control: what it takes to raise venture capital.

• What investors actually look for and how to make it easier for them to say yes.

• The psychology behind a VC’s biggest fear (and how to leverage it).

• Why warm introductions and investor networks are crucial.

• Reasons that transparency and consistency are key in VC due diligence.

• Red flags that make term sheets a dealbreaker for founders and funders.

• One thing that VCs really want to know: can you do it again?

Links Mentioned in Today’s Episode:

User Interviews

Basel Fakhoury on LinkedIn

Basel Fakhoury on X

Entrepreneurs Roundtable Accelerator (ERA)

The Lean Startup

Paige Soya

K Street Capital

K Street Capital on YouTube

Greg unpacks the journey of growing a family business into a brand that was valued at $300M+ at its peak. From navigating the fallout of the pandemic to ultimately filing for Chapter 11, his story is one of grit and perseverance.

He also opens up about his new book, “Undressed: The Unfiltered Story of My Failed American Dream and How It Led to Success,” offering a candid look at the lessons learned along the way.

A fitting close to a season all about exits—don’t miss this one.

Greg’s book- https://www.amazon.com/Undressed-Unfiltered-Failed-American-Success/dp/0960127704

Connect with us here:

1. Greg Vetter: https://www.linkedin.com/in/gregvetter/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Dimitry reflects on the challenges of validating key information, noting that diligence often means asking the same question in multiple ways to uncover inconsistencies.

They discuss the importance of trusting your instincts during the diligence process and how open, honest communication can make or break a successful transaction.

Connect with us here:

1. Dimitry Gershenson: https://www.linkedin.com/in/dgershenson/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Alli Cavasino and Natalie Poston, founders of JoyLet, built a no-frills “rent-the-runway” model for baby gear, allowing parents to rent items for the time they need.

In EP 19 of High Stakes, Alli and Natalie join Paige Soya, Managing Partner of K Street Capital, to discuss the exit and how they navigated the roadblocks in their journey.

Connect with us here:

1. Alli Cavasino- https://www.linkedin.com/in/allicavasino/

2. Natalie Poston- https://www.linkedin.com/in/natalieposton/

3. Paige Soya: https://www.linkedin.com/in/paigesoya/

4. K Street Capital: https://www.linkedin.com/company/kstreetvc/

00:00 Introduction

00:47 Meet the Founders: Ali and Natalie

01:41 The Birth of Joylette

04:41 Early Challenges and MVP Development

05:38 Raising Capital and Going Full-Time

07:31 Learning and Pivoting the Business Model

09:34 Customer Acquisition Strategies

16:43 Deciding to Exit

19:34 The Exit Process

24:43 Reflections and Future Plans

In this episode of High Stakes, Todd Bracher joins Paige Soya to answer.

With over 20+ years experience in building great products, Todd believes that the world’s biggest problems already have solutions, but they need the right design approach to shine.

They discuss:

- how better design can give your patent the moat it needs

- TRLs and IP litigation attorneys

- making a product market-ready

Don’t miss out.

Connect with us here:

1. Todd Bracher: https://www.linkedin.com/in/toddbracher/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Resources:

1. Design in Context (Todd’s book)- https://www.toddbracher.com/book

2. Market Efficiency Index (Free tool for founders/investors)- https://www.toddbracher.com/mei

But getting there was no walk in the park.

In this episode of High Stakes, K Street Managing Partner Paige Soya is joined by Scott Tilton, exited co-founder of Hookit.

They discuss:

• how Hookit got acquired for 2x the offer price

• why co-founders need to be aligned before the big close

• embracing the shift to becoming an employee after a merger

Connect with us here:

1. Scott Tilton: https://www.linkedin.com/in/tiltcore/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Personal data is more vulnerable than ever, and cybercriminals are ready to take advantage.

That’s where PrivacyHawk steps in — your defense against this growing digital chaos.

We're thrilled to have backed PrivacyHawk in its recent $3M funding round.

In this conversation with Aaron Mendez, CEO of PrivacyHawk, we discuss everything from dead weight on your cap table, the need for a better understanding of liquidation preferences, and why you're better off selling early rather than too late.

Connect with us here:

1. Aaron Mendes: https://www.linkedin.com/in/mendes/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

In this encore episode, hosted by Paige Soya, Richard Leggett, former CEO of FrontierView, and lead investor Tom McCormick dive into the harsh realities of the world of M&A.

They share how they navigated the pressures of competing priorities, kept the business afloat during the pandemic, and avoided a fire sale by strategically positioning for a successful exit.

With candid insights on resilience, timing, and critical decision-making, this episode is a must-watch for entrepreneurs facing tough choices.

Note: This episode is a re-upload with added substance and a quick sneak peak into the conversation at the start. Enjoy!

• How financial leverage and perfect timing led to Zach's career-defining $100M exit

• Insider tips on maximizing returns from high-growth investments

• Crucial lessons on negotiation power dynamics and maintaining control

Zach's candid insights on market timing, profit-taking, and strategic flexibility are pure gold. Don't miss this masterclass in entrepreneurial wisdom!

On this episode of High Stakes, Russ Hiddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox.

In this chat with Managing Partner Paige Soya, they discuss funding, exits, Russ’s next venture, Distill (hint: think Wikipedia but for company and people summaries).