Alle afleveringen
78 afleveringen, van nieuw naar oud
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How VCs Think About PR for Startups | Paige Soya & Kate Meissner (Velocity Partners)
5 november 2026 · 44 min
In this episode of High Stakes, K Street Capital Managing Partner Paige Soya continues the Venture Capital 101 season with a conversation about public relations (PR) for early-stage companies: when startups should invest in PR, how founders can build a compelling company narrative, and why the right media strategy can help accelerate business growth. Lees meer
She's joined by Kate Meissner, K Street investor and co-founder of Velocity Partners, a strategic communications firm working with venture-backed startups. Kate breaks down how founders should approach PR with limited resources, why publicity needs to start with clear business objectives, and how companies can identify the right moment to share their story with a broader audience.
Paige and Kate explore how founders can develop a narrative that resonates with investors, customers, employees, and journalists. They discuss what makes a story newsworthy, why reporters prioritize their readers over the companies they're covering, and how founders can build relationships with journalists before their biggest announcements.
The conversation also covers how AI is changing the media landscape, the rise of generative engine optimization (GEO), and why human relationships, credibility, and authentic communication may become even more valuable as more content becomes machine-generated. The episode closes with Kate's career journey, lessons from balancing entrepreneurship and family, and why founders should be selective about whose advice they follow.
We dive into
What PR means for early-stage startups and why it matters
How founders should approach PR with limited resources
Why publicity should start with clear business objectives
When startups are ready to invest in PR and media exposure
How founders can identify a compelling company narrative
Why finding product-market fit can be a signal to amplify your story
How PR can support fundraising, hiring, and customer acquisition
How strategic product announcements can bu…
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The 6 Unit Economics VCs Use to Evaluate Startups | Paige Soya, Nick Duafala & K Street Capital
15 oktober 2026 · 43 min
In this episode of High Stakes, K Street Capital Managing Partner Paige Soya and Principal Nick Duafala continue the Venture Capital 101 season with a discussion about unit economics: how investors evaluate a company's financial performance, efficiency, and potential to scale. Lees meer
Joined by members of K Street Capital's investment team, Paige and Nick break down the key metrics the firm looks at when evaluating startups, particularly SaaS businesses, and explains why founders should understand their expected economics even before generating revenue.
The conversation covers lifetime value to customer acquisition cost (LTV), gross margins, CAC payback period, churn, net revenue retention, and the efficiency of revenue growth. The team explains what healthy benchmarks can look like, why the direction of a metric matters just as much as its current value, and how founders can use these numbers to make better business decisions.
They also explore how AI is changing traditional SaaS economics, why higher infrastructure costs can sometimes make sense when growth justifies them, and why investors need evidence before changing their benchmarks. The episode closes with a discussion about adapting to uncertainty, lessons from career mistakes, and the importance of communication and teamwork.
We dive into
What unit economics mean and why VCs evaluate them at the seed stage
Why founders should model expected economics before generating revenue
How investors evaluate the LTV ratio and what a 3–5x ratio can indicate
Why SaaS businesses typically aim for 70–90% gross margins
How business models influence gross margin expectations
Why improving financial metrics can matter more than hitting a benchmark today
How AI companies are challenging traditional SaaS margin expectations
What CAC payback period tells investors about customer acquisition efficiency
How churn and net revenue retention affect customer lifetime value
Why revenue growth needs to be evaluated alongside pr…
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Zero Churn, 90% Close Rate: The Customer Journey VCs Look For | Paige Soya & Mike Desai (CEO, Truentity Health)
2 oktober 2026 · 35 min
In this episode of High Stakes, K Street Capital Managing Partner Paige Soya continues the Venture Capital 101 season with a conversation about the user journey: how products get sold, activated, and adopted, and why VCs pay close attention to it. Lees meer
She’s joined by Mike Desai, co-founder and CEO of Truentity Health, which gives independent pharmacies, many serving rural communities, the infrastructure to provide chronic care programs to their patients.
Mike explains how Truentity’s sales process often takes just one or two calls and why he actively disqualifies customers who aren’t ready. He also walks through the 21-day onboarding process and “go live day” that help drive adoption and retention—and shares how he built founder-market fit without a pharmacy background.
Paige and Mike discuss the work behind zero churn, why pricing needs to support a hands-on customer experience, and what founders can learn by spending time inside their customers’ businesses. The episode closes with the best advice Mike has received: people buy from people.
We dive into
Why VCs look closely at the customer journey when evaluating a business
How Truentity uses cold calls and converts more than 90% of demos into contract requests
Why qualifying customers includes knowing when they aren’t ready
Building founder-market fit by starting with a services business
The checklists, training, and on-site support behind Truentity’s 21-day go-live process
How dedicated Slack channels provide real-time customer support
Why pricing and annual contract value need to support the customer experience
Why every new hire attends a customer onboarding, regardless of role
Mike’s early-morning routine, running, and lessons from working at eight startups
Why human connection still matters in sales
Chapters
00:00 Intro
00:54 Welcome to High Stakes: VC 101 & the user journey
01:38 Meet Mike Desai & Truentity Health
04:09 Why the user journey matters to VCs
05:00 Cold calling, customer qualific…
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How VCs Actually Think About Startup Valuations? | Paige Soya, Nick Duafala & K Street Capital
17 september 2026 · 39 min
What actually determines what a startup is worth? Lees meer
In this episode of High Stakes, K Street Capital’s Paige Soya and Nick Duafala are joined by investment team members Joseph and Jose for a Venture Capital 101 breakdown of how VCs assess startup valuations and why it’s rarely as simple as founders might assume.
The conversation begins with the core VC perspective: valuation isn’t based solely on what a company is worth today. Investors are also considering what it could be worth at exit, how long it may take to get there, and whether the potential return aligns with the fund’s strategy and portfolio construction.
The team walks through valuations at each stage, from pre-seed and seed to Series A and growth, and explains how the criteria evolve. At the earliest stages, the focus is heavily on the founder, vision, and technology. As a company matures, product-market fit, comparable financings, revenue quality, customer diversification, margins, and scalability become increasingly important.
Paige and Nick also unpack the terms beyond the headline valuation that can materially affect a deal, including warrants, liquidation preferences, board seats, and pro rata rights. They discuss what “founder-friendly” investing means in practice, how cap tables may be restructured during challenging markets, and what investors learned from the wave of recapitalizations that followed the 2022 market downturn.
The conversation then gets granular about revenue multiples: how growth, churn, customer concentration, market size, and revenue quality can move a multiple up or down. The team closes by exploring the “founder premium” earned by proven repeat entrepreneurs, followed by a lightning round on the best advice each person has received.
In this episode:
How VCs assess startup valuations
Why fund strategy and portfolio construction influence valuation
What investors evaluate at the pre-seed, seed, Series A, and growth stages
Typical valuation ranges across funding stages
W…
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What Makes a Business VC-Backable? | Paige Soya, Nick Duafala, & Jon Sherry (Alium, Ex-CB Insights)
11 september 2026 · 49 min
What makes a business venture-backable? Lees meer
In this episode of High Stakes, K Street Capital’s Paige Soya and Nick Duafala sit down with Jonathan Sherry, founder and CEO of Alium and former co-founder of CB Insights, for a Venture Capital 101 discussion about the business models VCs evaluate and what makes them scalable, defensible, and fundable.
The conversation covers the fundamentals of SaaS and marketplaces, what constitutes a true platform, and why founders should understand the distinction between a business model and a pricing model. Jonathan also shares how CB Insights and Alium have used subscription models, seat- and capability-based pricing, and marketplace dynamics to monetize their businesses.
The group then explores one of the biggest shifts in technology: AI and the rise of usage-based and labor-replacement models. They discuss whether AI will fundamentally change SaaS, why customers increasingly want to experiment before committing to annual contracts, and what founders should understand about consumption, utilization, pricing, and ROI.
The episode also examines what VCs look for beyond ARR, including customer concentration, ACVs, renewals, paid POCs, and evidence that a company has built a repeatable business model.
Finally, the conversation turns to liquidity in venture capital. With companies remaining private longer and fewer pursuing IPOs, the group discusses M&A, secondary markets, alternative paths to liquidity, and why exits in the $100 million to $250 million range can be compelling outcomes for early-stage investors.
In this episode:
What makes a business model VC-backable
Why SaaS remains a compelling venture business model
How marketplaces and platforms create defensibility
Why a “platform” is not necessarily a business model
How startups can evolve their business models as they grow
The emerging “service as software” and labor-replacement model
How AI is accelerating the shift toward usage-based pricing
The risks and opportuni…
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Learn the Lingo VCs Actually Use | Paige Soya, Nick Duafala, & K Street Capital
20 augustus 2026 · 42 min
For years, founders and investors have used terms like “fintech,” “SaaS,” and “platform” without always having a shared definition. But as venture firms rely more heavily on data to track deals, returns, and portfolio performance, getting that language right matters more than ever. Lees meer
In this episode of High Stakes, Paige Soya and Nick Duafala are joined by K Street Capital’s Joseph Whang and Jose Cifuentes for a Venture Capital 101 breakdown of how VCs classify the startups they evaluate.
Using real-world examples from Salesforce, Airbnb, Facebook, and Auth0, the team walks through the eight categories that make up K Street’s internal deal taxonomy, why consistent classification matters, and how founders can use the same framework to better understand, and communicate, their businesses.
In this episode:
The eight categories we use to classify startups
Why a company’s industry and its customer’s industry aren’t necessarily the same
How B2B, B2C, B2G, and dual-use define customer type
Why go-to-market motion—direct, enterprise, product-led, or channel—matters to investors
How VCs think about business and revenue models
The difference between product type and technology category, and why AI increasingly cuts across both
What separates a true platform from a suite of products or services
How K Street uses AI internally to keep deal data consistent and comparable
Whether you’re a founder refining your fundraising narrative or a new investor learning the language of venture capital, this episode is a practical guide to how VCs actually think about and categorize the companies they evaluate.
Topics: Venture Capital • Startup Fundraising • Startup Taxonomy • Business Models • Go-to-Market Strategy • SaaS • Marketplaces • Venture Investing • Founder Advice • Startup Strategy
Timestamps
00:00 – Cold open: The data problem behind bad taxonomy
00:58 – Welcome to High Stakes: VC 101
02:04 – Meet the deal team: Joseph & Jose
05:09 – The 8 categories of startup ta…
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Go-to-Market Is the Moat | Paige Soya, Nick Duafala, and Mark Schacknies (NFTYDoor)
6 augustus 2026 · 46 min
What actually creates a competitive moat? Lees meer
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 Duafala are joined by Mark Schacknies, CEO & Co-Founder of NFTYDoor—a company K Street backed in its earliest stages after recognizing the strength of its distribution strategy. NFTYDoor went on to become one of the country's leading white-label HELOC platforms, serving 500+ lenders, 36,000+ mortgage loan officers, and approaching $7B in annual run-rate volume before its successful exit.
Using NFTYDoor's journey as a case study, they explore why venture investors increasingly evaluate go-to-market execution alongside technical differentiation, how AI is reshaping startup defensibility, and what founders should focus on to build businesses competitors can't easily replicate.
In this episode:
What venture capitalists mean by a competitive moat
Why product-market fit comes before scalable distribution
How distribution becomes a durable competitive advantage
The role of network effects and switching costs
Why founders should understand—not avoid—the competition
How focus creates defensibility in crowded markets
Why customer discovery matters more than the perfect pitch
Practical advice for founders raising venture capital
Whether you're building a startup, evaluating investment opportunities, or interested in how venture capitalists think about competitive advantage, this episode provides actionable insights into building durable businesses in the AI era.
Topics: Venture Capital • Startup Fundraising • Competitive Moats • Startup Strategy • Product-Market Fit • Distribution Strategy • Network Effects • Switching Costs • Founder Advice • Go-to-Market Strategy • Startup Growth • Venture Investing
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How VCs Structure Venture Deals | Paige Soya, Nick Duafala & Scott Stern (Partner, Origin Ventures)
23 juli 2026 · 52 min
Not all venture deals are created equal, and understanding the fine print can make a significant difference for founders. Lees meer
In this episode of High Stakes, K Street Capital's Paige Soya and Nick Duafala are joined by Scott Stern, Partner at Origin Ventures, to break down how venture capital deals are actually structured. From SAFEs and convertible notes to priced equity rounds, founder vesting, liquidation preferences, pro rata rights, and anti-dilution provisions, they explain the terms that shape startup financings—and why they matter for both founders and investors.
Along the way, the conversation explores common fundraising mistakes, why complicated cap tables can derail future financing rounds, and how founders can approach term sheet negotiations with greater confidence. Rather than simply defining venture terminology, this episode explains the reasoning behind the structures investors use and how those decisions can influence a company's long-term success.
Whether you're raising your first round, investing in startups, or simply looking to better understand venture capital, this episode offers practical insights into one of the most important—and most misunderstood—aspects of startup fundraising.
In this episode:
The differences between SAFEs, convertible notes, and priced equity rounds
How valuation, dilution, and cap tables really work
Why founder vesting exists and what investors are protecting
Liquidation preferences, option pools, and anti-dilution explained
Pro rata rights and why investors negotiate for them
Common fundraising mistakes founders should avoid
How to approach your first venture capital term sheet with confidence
Guest:
Scott Stern, Partner at Origin Ventures
Hosts:
Paige Soya, Managing Partner, K Street Capital
Nick Duafala, Senior Principal, K Street Capital
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How VCs Evaluate Pre-Revenue Startups | Paige Soya, Nick Duafala & Charles Hudson (Precursor Ventures)
9 juli 2026 · 35 min
What makes a pre-revenue startup worth investing in? Lees meer
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 and an idea when so much is still uncertain?
In this episode of High Stakes, Paige Soya and Nick Duafala sit down with Charles Hudson, Managing Partner at Precursor Ventures, to explore how investors evaluate startups at the earliest stages of venture.
Charles shares his framework for pre-seed investing, including how he assesses founder insight, market timing, perseverance, resourcefulness, and a founder's ability to turn an early hypothesis into a scalable company.
The conversation explores what separates exceptional founders from the rest—and why, at the pre-seed stage, investing is often as much about the founder as it is about the business.
In this episode, we discuss:
Why pre-revenue investing requires a different approach than later-stage venture investing
The two founder archetypes Charles sees most often: industry insiders and "naive outsiders"
How investors determine whether a founder has a unique and durable insight
Why proximity to a problem can be one of a founder's greatest advantages
The difference between product innovation and business model innovation
Why distribution strategy can matter just as much as the product itself
How VCs evaluate founders when there is little customer or revenue data
Why resourcefulness and perseverance are two of the strongest predictors of founder success
How market timing influences pre-seed investment decisions
Why being slightly late can sometimes be better than being too early
What Charles learned from founders who succeeded inside large companies but struggled as startup CEOs
How resilience and life experiences shape a founder's ability to navigate uncertainty
Key Takeaways
Great founders don't always have the most experience—they have the strongest i…
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Venture Liquidity, Secondaries & How VCs Exit | Paige Soya, Nick Duafala & Andrew (Principal at Savano Capital)
25 juni 2026 · 36 min
How do venture capital firms actually exit their investments when startups are staying private longer than ever before? Lees meer
On this episode of High Stakes, hosts Paige Soya and Nick Duafala sat down with Andrew Seter, Principal at Savano Capital, to unpack venture liquidity, the growing secondary market, and how founders, employees, and investors are accessing liquidity outside of traditional IPOs and acquisitions.
As private companies delay public offerings and remain private for longer periods of time, secondaries have become an increasingly important part of the venture ecosystem. But what exactly are they, who benefits from them, and why has the market grown so rapidly?
In this episode, we discuss:
What venture secondaries are and how they work
The difference between primary and secondary transactions
Why startups are staying private longer
The rise of the secondary market and what is driving its growth
How founders, employees, and investors access liquidity before an IPO
Why secondaries are becoming a critical component of venture capital exits
The future of private market liquidity
Whether you're a founder, operator, investor, or simply curious about how venture capital works behind the scenes, this episode breaks down one of the fastest-growing areas of private markets in an approachable way.
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VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)
11 juni 2026 · 37 min
How long does it actually take to raise venture capital? Lees meer
In this episode of High Stakes, Paige Soya and Nick Duafala sit down with Matt Bressler, Co-Founder and General Partner at Lookout Ventures, formerly TDF Ventures, to discuss venture capital deal timelines, fundraising momentum, and the diligence process that takes place behind every investment decision.
From initial founder meetings to signed term sheets, they explore what causes fundraising processes to move quickly, what causes deals to stall, and why many of the fastest investments begin months—or even years—before a company officially starts raising capital.
Topics covered include:
Venture capital deal timelines
How investors evaluate startup opportunities
What creates fundraising momentum
Preparing for investor due diligence
Common fundraising mistakes founders make
Building investor relationships before a raise
Why some venture deals move faster than others
Whether you're raising your first round, preparing for a future fundraise, or simply interested in how venture capital works behind the scenes, this episode offers practical insights into how investors build conviction and make investment decisions.
Subscribe for more conversations with founders, investors, and operators shaping the startup ecosystem.
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Power Dynamics in VC | Paige Soya, Nick Duafala, Haley Bryant (Hustle Fund), & Ann Marie Guzzi (Dalmatian Ops, Angel Investor & Agora Initiative)
28 mei 2026 · 52 min
In this episode of High Stakes, K Street Capital’s Paige Soya and co-host Nick Duafala sit down with Haley Bryant, Partner at Hustle Fund, and Ann Marie Guzzi, angel investor, Managing Partner of Dalmatian Ops and Co-Founder of The Agora Initiative, for a deep dive into one of the most misunderstood topics in venture capital: power dynamics. Lees meer
From the moment a founder starts fundraising to the moment a company exits, who actually has the power, and how does that shift over time?
The conversation breaks down:
Who really makes investment decisions inside VC firms
How LPs influence deal flow and investor conviction
Why founders often underestimate their leverage
The hidden dynamics between associates, partners, and investment committees
How governance changes after the check gets written
Why founder-investor alignment matters at exit
IPOs vs M&A vs secondary transactions
How board control and voting shares shape outcomes
Why relationships and reputation matter throughout the venture ecosystem
Along the way, the group shares candid insights on:
Why fundraising feels a lot like dating
The difference between scarcity and abundance mindsets
What happens behind the scenes during diligence
How market conditions shift founder leverage
Why the best founders ultimately hold more power than they realize
Whether you’re a founder raising your first round, an emerging investor, or simply curious about how venture capital actually works behind closed doors, this episode offers an honest look at the incentives, relationships, and structures that shape startup outcomes.
Subscribe to High Stakes for more conversations breaking down the realities of venture capital, startups, and company building.
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How VCs Evaluate Founding Teams | Paige Soya, Nick Duafala, & Neil Shah (CEO, ThinkNimble)
14 mei 2026 · 42 min
Most people assume VCs are evaluating traction, revenue, or the pitch deck first. Lees meer
Those things matter — but often, the real signal is something harder to quantify: how a founder thinks.
In this episode of High Stakes, Nick Duafala and I sat down with Neil Shah (CEO of ThinkNimble) to unpack how investors actually evaluate founding teams — especially in a market where AI is fundamentally changing how companies get built.
A few take aways:
→ You can often tell within the first 15–20 minutes whether a founder has the qualities you want to back.
→ Investors are ultimately evaluating the quality of thinking behind the business — not just the business itself.
→ As AI removes more of the execution friction, thoughtful strategy, judgment, and founder insight become even greater differentiators.
We also get into:
Why second-time founders often have an edge
How AI is changing startup team design
What “deep thinking” actually looks like in founders
Why pattern recognition still matters in venture
What investors are really evaluating in that first meeting
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Angel Investors vs. VCs | Paige Soya & Dadi Akhavan (Startup-to-IPO Founder)
30 april 2026 · 40 min
In this episode of High Stakes, Paige Soya sits down with Dadi Akhavan, a startup-to-IPO founder and angel investor, to break down one of the most important dynamics in early-stage investing: angel investors vs venture capitalists. Lees meer
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.
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How VCs Source Deals | Paige Soya, Nick Duafala & Taylor Margot (Partner, Lytical Ventures)
16 april 2026 · 50 min
How do venture capitalists actually find deals and how can founders break into those conversations? In this episode of High Stakes, Paige Soya and Nick Duafala are joined by Taylor Margot (Partner at Lytical Ventures) to break down one of the most important, and often misunderstood, parts of venture capital: deal sourcing. They unpack where deals really come from, from warm referrals and deep networks to unexpected moments of curiosity, and why the strongest opportunities are often driven by relationships, not cold outreach. The conversation goes beyond surface-level advice to explore how sourcing has evolved, the role of personal brand, and why depth matters more than breadth in today’s market. For founders, this episode is a playbook. The group shares practical strategies for getting in front of VCs, from leveraging your network the right way to standing out at events, and what not to do if you want to build lasting investor relationships. They also dive into the psychology behind cold outreach, why most inbound gets ignored, and how to increase your odds of getting that first meeting. Whether you're an investor looking to build deal flow or a founder trying to raise capital, this episode offers a clear, tactical look at how connections actually turn into deals and how to position yourself on the right side of that equation. What you’ll learn: -How VCs really source deals (and why it’s not just about “who you know”) -The difference between warm intros, cold outreach, and organic discovery -Why deep relationships outperform wide networks -How founders can effectively get in front of investors -The biggest mistakes founders make when approaching VCs -Why venture is a long game—and how to play it Lees meer
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Not All Capital Is Created Equal: Venture Capital vs. Other Funding | Paige Soya & Jill Ralph (Former Chemonics Capital and Motley Fool)
2 april 2026 · 32 min
Venture capital is one of the most misunderstood asset classes in investing and one of the most powerful when approached correctly. Lees meer
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.
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An Introduction to Venture Capital: Meet your hosts | Paige Soya & Nick Duafala at K Street Capital: Season 4 of High Stakes
12 maart 2026 · 36 min
Welcome to Season 4 of High Stakes and this season we’re starting with the fundamentals. Lees meer
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.
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Unlocking Women Investing in VC with Julie Castro Abrams
9 december 2025 · 47 min
In this episode of High Stakes, host Paige Soya, Managing Partner at K Street Capital, sits down with Julie Castro Abrams, GP and Founder of How Women Invest, for a candid look at one of the most important shifts happening in venture capital today: the surge of women stepping in as LPs, angel investors, and fund leaders. Lees meer
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
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What VCs and Angel Investors are seeing from Y-Combinator in 2025
20 november 2025 · 48 min
In this episode of High Stakes, K Street Capital Managing Partner, Paige Soya, sits down with Gabriel Jarrosson, Managing Partner at Lobster Capital, to unpack how Y Combinator’s internal tool “Bookface” is reshaping investor-founder relationships in 2025. Lees meer
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.
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How Early Funding Rounds a Shape Startup's Future
6 november 2025 · 38 min
The High-Stakes Decisions Behind Early Fundraising: When to Raise, Who to Raise From, and How Much Equity to Give Up Lees meer
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.
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How Diverse Founders Drive Bigger Wins
23 oktober 2025 · 39 min
Many investors still see backing diverse founders as a bigger risk. Lees meer
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.
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The Art and Science of Diligence in Early-Stage VC
9 oktober 2025 · 47 min
How do investors evaluate founders when there’s little or no traction? What really drives decisions in early-stage venture capital? Lees meer
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.
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How VC success is truly measured
25 september 2025 · 42 min
How do you know if you're actually a successful venture capitalist? It's harder to tell than you might think. In this episode, K Street Capital Managing Partner Paige Soya sits down with Henri Pierre-Jacques, Managing Partner of Harlem Capital, to dive deep into the metrics that really matter in venture capital - and why most of them have nothing to do with spreadsheets. Lees meer
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.
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What LPs Want from VC Fund Managers
11 september 2025 · 36 min
Most founders know the pressure of fundraising, but what many don’t realize is that venture capitalists have to fundraise too. Behind every investment is a group of limited partners (LPs) whose expectations shape how funds operate, the kinds of companies they back, and even the way they communicate with founders. Lees meer
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.
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Power Law & the VC Playbook
28 augustus 2025 · 46 min
What makes a venture investment a true home run—and why is it so hard to find those opportunities? Lees meer
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.
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The Relationship between Check Size, Ownership Percentage and Stage in VC Investing
14 augustus 2025 · 34 min
“The Ownership Equation: Why Check Size, Stage, and Strategy Matter in VC” Lees meer
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.
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Dual Threat CEOs
6 augustus 2025 · 38 min
At K Street, we’ve had the privilege of backing some incredible founders and over time, one theme has become increasingly clear: The most impactful leaders aren’t just building great companies, they’re also investing in others. These are dual threat CEOs: founders who play both offense and defense. They're scaling their own ventures while also writing early checks, mentoring rising entrepreneurs, and giving back to the ecosystem that helped them succeed. In the latest episode of High Stakes, K Street investor Sara Fagen joined Paige Soya to unpack what that role really looks like and why it matters. She shared a powerful perspective on how investing can be a vehicle for impact especially for new founders who have big ideas but lack access or experience. These early-stage bets often start with a conversation, a relationship, and a belief that someone just needs their first chance. That’s the ethos we carry at K Street. We back operators who pay it forward and we’re proud to count so many dual threat CEOs in our portfolio and community. Lees meer
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Why VCs Care About Board Seats | Brian Goldsmith, Co-founder & Partner at Avenue Growth Partners
17 juli 2025 · 42 min
Ever wonder why venture capitalists fight for board seats? It's not just about control or fancy dinners. In this episode, Paige Soya (Managing Partner, K Street Capital) sits down with Brian Goldsmith (Managing Partner, Avenue Growth Partners) to pull back the curtain on board governance in venture capital. Lees meer
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.
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The Unseen Work of Venture Capital | James Barila, Executive Director of Station, DC
3 juli 2025 · 38 min
There’s a lot to love about working in venture capital but there’s also a lot of hard, often overlooked work that doesn’t make the headlines. Lees meer
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.
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Habits of Highly Successful Founders | Alex Wirth, CEO of Quorum
20 juni 2025 · 40 min
What separates successful founders from the rest? Lees meer
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.
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Landing a job in VC | Myrto Lalacos
5 juni 2025 · 36 min
In this episode of High Stakes, host Paige Soya sits down with Myrto Lalacos, Principal at VC Lab, for an in-depth conversation on landing a job in VC. Myrto shares her unique career journey—from leading accelerator programs in the UK to co-founding a B2B SaaS fund and launching the Venture Institute, an initiative aimed at connecting diverse, emerging talent with pathways into VC. Together, Paige and Myrto explore what it really takes to be a fund manager, and the often-overlooked skills critical to running a venture firm—not just sourcing deals.What Lees meer
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
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The Cold, Hard Truth About Startup Shutdowns | Dori Yona
22 mei 2025 · 42 min
What really happens when a startup shuts down? In this revealing episode of High Stakes, host Paige Soya sits down with Dori Yona, founder of SimpleClosure and seasoned entrepreneur, to unpack the complex—and often hidden—realities of shutting down a startup. After navigating the painful process of closing his own VC-backed company, Dori realized just how broken and opaque the process was, and became determined to fix it. Now, after guiding over 500 shutdowns in 2024 alone, he brings clarity to a topic most founders and investors would rather avoid. From legal minefields and IP entanglements to payroll risks and emotional tolls, Dori shares what every stakeholder needs to know about ending a startup the right way.Key Points From This Episode: Lees meer
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.
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When Venture Deals Go South: Inside the Realities of Startup Failures, Wind Downs, Write-Offs, and Zombie Companies
8 mei 2025 · 39 min
Not every startup story ends in a big exit. Sometimes, despite best efforts, companies miss key milestones, burn through their runway, or become what investors call “zombie startups.” Lees meer
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.
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Why Some VCs Lead and Others Don’t | Mark Volchek
24 april 2025 · 42 min
Why do some VCs lead while others follow? On this episode of High Stakes, host Paige Soya sits down with Mark Volchek, founding partner at Las Olas Venture Capital, to explore the dynamics of leading versus following in venture capital. With a focus on early-stage B2B software, Mark brings insights from his journey, from founding a FinTech company during the dot-com crash to launching and managing multiple successful funds since 2016. Together, they unpack the pros and cons of leading investment rounds, how firm size and resources influence strategy, and how to navigate key decisions like taking board seats, aligning with co-investors, and allocating resources. Mark also shares advice for founders on finding the right VC fit and explains why there is a firm out there for every type of startup. Tune in for a deep dive into how venture firms decide when to lead and when to follow, and what that means for investors and founders alike! Lees meer
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.
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Breaking Into Venture—No Straight Paths, Just Bold Moves | Ethan Austin
11 april 2025 · 56 min
How do you make it in venture capital when the path is anything but straightforward? In this episode of High Stakes, Ethan Austin, Founding Partner at Outside VC, shares his journey and the key lessons he's learned as a founder in the world of early-stage investing. From the importance of empathy and people skills over traditional finance experience to the power of networking and taking bold, unconventional actions to set yourself apart, Ethan breaks down what it takes to succeed in VC. He also reveals why storytelling, strategic name-dropping, and putting your own capital on the line can make all the difference in your career. Whether you're looking to break into the industry or refine your approach, Ethan's insights will help you navigate the highs and lows of venture capital success. Tune in to learn how to leverage relationships, embrace failure, and become a smarter, more resilient investor! Lees meer
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.
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How Government Policy Shapes VC-Backed Startups: Lessons from Softbank | Bruce Andrews
27 maart 2025 · 35 min
When choosing to invest in a company, there are a lot of elements for VCs to consider—and government policy is no exception. Today on High Stakes, we explore the role of government policy in venture capital and its impact on the industry. Joining Paige Soya to break it all down is Bruce Andrews, who has spent the last 30+ years at the intersection of business, public policy, and politics. Over his career, he’s occupied a range of consequential roles, both in government and commerce, from Deputy Secretary of the US Department of Commerce to Vice President for Global Public Policy at SoftBank. Bruce unpacks the ways government policies affect VCs, how a change in administration can impact startups, and what companies should do to prepare. He sheds light on his time at SoftBank and what it taught him about the VC industry before expanding on how the company helped startups by giving them access to government affairs experts. We also hear Bruce’s reflections on failure and success, his advice to listeners, and more. Join us for a fascinating exploration of government policy and its impact on the industry of venture capital! Lees meer
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,…
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Fundraising from VCs: Game Changing Insider Tips | Basel Fakhoury
13 maart 2025 · 43 min
What would you do if you spent two years working relentlessly on a startup idea only to realize no one wants it? That’s exactly what happened to Basel Fakhoury before he and his co-founders scrapped their first business and pivoted to User Interviews, a platform that has now raised $45 million in venture capital. In this episode of High Stakes, Paige Soya sits down with Basel to break down what it really takes to raise money from VCs, from navigating rejections to mastering the fundraising narrative. They cover the art of building investor relationships (spoiler alert: it’s a long game!), the must-have data points and deal terms that can make or break a pitch, why a strong financial story matters just as much as traction, and how User Interviews transitioned from a scrappy Craigslist hustle to a SaaS powerhouse. Plus, Basel shares the biggest mistake he made as a founder and the fundraising strategy that changed everything. Lees meer
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
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The End Is Not the End | Greg Vetter
5 december 2024 · 35 min
In the final episode of Season 2, K Street Capital’s Managing Partner, Paige Soya, sits down with Greg Vetter—the driving force behind Tessemae’s, one of the nation’s most iconic condiment brands. Lees meer
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/
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Why Transparency Can Make or Break a Transaction | Dimitry Gershenson
22 november 2024 · 23 min
In this episode of High Stakes, Dimitry Gershenson shares how his team tackled the operational and financial diligence required to pull it off, in this conversation K Street Capital’s Managing Partner, Paige Soya. Lees meer
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/
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How This Georgetown MBA Class Project Got Acquired by GoodBuy Gear | Alli Cavasino & Natalie Poston
7 november 2024 · 30 min
What started as an MBA class idea led to an acquisition by one of the nation’s leading baby and kid gear marketplaces. Lees meer
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
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Leverage IP For A Winning Exit | Todd Bracher & Paige Soya
24 oktober 2024 · 25 min
How do you leverage intellectual property for M&A? Lees meer
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
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What No One Tells You Before Getting Acquired | Scott Tilton
16 oktober 2024 · 42 min
Hookit was acquired by KORE Software for much more than the $20 million they raised over three funding rounds. Lees meer
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/
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The Strategic Rationale Behind Early Exits | Aaron Mendes & PrivacyHawk
26 september 2024 · 46 min
Managing our digital footprints has become almost impossible without the right tech. Lees meer
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/
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M&A Lessons Every Entrepreneur Needs To Know | Richard Leggett & Tom McCormick
12 september 2024 · 43 min
Building a company for exit? Prepare for the long haul. Lees meer
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!
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3 Exit Strategies That Changed Everything, Featuring Zach Axelrod
29 augustus 2024 · 26 min
In this episode of High Stakes, host Paige Soya dives in with Zach Axelrod, CEO of Redball Energy, uncovering the game-changing moments that shaped his entrepreneurial success. Discover: Lees meer
• 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!
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How This Entrepreneur Sold His Startup To Dropbox For $165M | Russ Heddleston
15 augustus 2024 · 29 min
Imagine thinking your startup is doomed, only to be acquired for $165M. Lees meer
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).
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Proactive Investment Exit Strategies: Insights from Marcus Brauchli
1 augustus 2024 · 31 min
In episode 12 of High Stakes, Paige Soya, Managing Director of K Street Capital, interviews Marcus Brauchli, co-founder of North Base Media and former managing editor at the Wall Street Journal, on the intricacies of investment exits. Marcus shares his extensive experience in the venture capital world, highlighting the lessons learned from both successful and failed exits. They cover the wide range of stories Marcus has to share on the importance of legal documentation, the complexities of international investments, and the various exit strategies companies may face. Marcus also emphasizes the necessity for founders to plan for exits from the beginning and maintain open communication with investors. Tune in for insightful advice on navigating the unpredictable landscape of venture capital exits. Lees meer
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Industry Dive's Expansion Strategy and Exit with Founder Sean Griffey
18 juli 2024 · 25 min
In Episode 11 of High Stakes, Paige Soya interviews Sean Griffey, CEO of Industry Dive. Griffey discusses Industry Dive's journey from bootstrap beginnings to a company with $100 million in revenue and over 400 employees, culminating in its acquisition by Falfurrias Capital. He emphasizes the importance of preparation and cultural fit in acquisitions. Griffey also shares insights into Industry Dive's subsequent acquisition by Informa in 2022, navigating the transition from private equity ownership to being part of a large public corporation, and the opportunities and challenges it brought. Lees meer
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Building Impactful Companies: Insights for Founders, Featuring Joe Fluet
6 juli 2024 · 30 min
In episode 10 of High Stakes, Paige Soya, Managing Partner at K Street Capital, and Joe Fluet, Founder of Fluet Law Firm and MAG Aerospace, discuss Fluet’s journey from founding MAG to navigating significant exits and recaps. He emphasizes a values-driven approach to business, discussing how aligning with investors who share these values is crucial for long-term success. Tune in to hear Fluet’s insights underscoring the complexity and critical decisions involved in building lasting, impactful companies. Lees meer
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Insights on IPOs and acquisitions from both sides of the table, featuring Martin Tobias
20 juni 2024 · 30 min
Join us as we dive into the world of multiple exits with Martin Tobias, Managing Partner of Incisive Ventures. Martin brings a wealth of experience and perspective as a GP and a three-time venture-funded CEO who has navigated IPOs and strategic acquisitions, sharing insights from his journey with Loud Eye Technologies, among others. He discusses the nuances of laddering and IPO pricing, the challenges of lock-up periods, and strategies for managing concentrated positions post-exit. Tune in to Martin and Paige’s discussion on the dynamics of modern exit strategies and valuable perspectives for both founders and investors. Lees meer