🎙️ Special Edition Podcast: How to Play the Valuation Game

This week’s Raise & Exit episode is different — it’s a live recording of Edgar Baum’s talk at the Silicon Y’all Conference, where nearly 100 SaaS and tech CEOs, VCs, and PE leaders gathered to unpack one question:

👉 What really drives your company’s valuation — and how can you influence it?

In this special session, Edgar walks through how founders can:
⚡ See beyond “industry average” multiples — and why they’re often meaningless
⚡ Identify what truly drives a premium: commercial model, timing, and scarcity
⚡ Use quarterly valuation discipline to turn intelligence into negotiating power
⚡ Build a “valuation playbook” to win your own exit championship

Whether you’re raising capital or planning your next exit, this talk reframes valuation as a strategic sport — not a math problem.

🎧 Listen to the full session: Raise & Exit Podcast – Live from Silicon Y’all

🎙️ Episode 18 is live! This time we sit down with Matt McDonnell, Managing Partner & co-founder of Stellifi VC and host of the Navigating Complexity podcast, to talk about what founders often overlook when raising capital and chasing product-market fit.

Matt brings a rare dual perspective as both a real estate investor and a venture capitalist — and his advice cuts through a lot of the noise founders hear about what “success” should look like.

What do we cover?

1. Success sits at the intersection of curiosity and steep learning: founders who follow problems they’re genuinely curious about unlock growth, even amid uncertainty.

2. Choosing capital is choosing a business model. Venture funding is a “one-way door”: once you take it, your business must operate on VC timelines and growth expectations. Raise late, and only when aligned.

3. Product-market fit is lived, not declared. True validation comes from customer behaviors — referrals, expansions, and inbound demand — not just hitting abstract metrics.

Matt also shares why geography matters less than people think, how knowledge asymmetry can be both an advantage and a trap, and why continuous learning is a founder’s best defense in fast-changing markets.

🎧 Tune in for a candid conversation on building smarter, scaling with intention, and choosing the right capital for your journey.

🎙️ New episode of Raise & Exit is live! This time we sit down with John James, host of the Champagne Strategy podcast and long-time growth strategist, to talk about what founders often get wrong when it comes to brand, growth, and go-to-market strategy.

John has spent 20+ years across agencies, startups, and Silicon Valley advising founders on cutting through myths and building companies that actually scale.

What do we cover?
1. Brand ≠ branding. A brand is human memory real estate — being remembered in the right category at the right time. Branding is the process of creating that memory. Confusing the two leads to wasted spend.

2. Early adopters aren’t your market. Those first 10–30 customers often buy because they know you. Real growth comes when strangers — who don’t trust you yet — decide to switch. That requires different triggers.

3. TAM is a trap. Investors love big TAM slides, but the real constraint is how many buyers are actually in market now and what it takes to make them switch from substitutes.

4. Beware the brand campaign myth. Agencies push early founders toward branding campaigns, but true brand equity comes from years of consistent acquisition and fulfillment — not glossy ads.

If you’re a founder wrestling with growth, positioning, or when to invest in brand, this episode is packed with lessons to help you avoid expensive mistakes.

🎧 Tune in for an unfiltered look at what actually drives growth vs. what’s just startup mythology.

🎙️ Episode 16 is live! This time we sit down with Neal Cobb, co-founder of EquityX, to talk about how founders of legacy businesses can think differently about exits — honoring employees, protecting culture, and creating value that lasts beyond the transaction.

If you’re a founder or owner planning for succession, this episode is full of hard-earned lessons on how to prepare for one of the most important transitions of your career.

What do we cover?

1. Exits are about more than profit. Many legacy business owners want a transition that protects their employees and preserves their brand, not just one that maximizes valuation.

2. Avoid inflated expectations. Some brokers promise unrealistic valuations to win business. Founders should focus instead on understanding the real drivers of value and aligning with buyers who share their priorities.

3. The sale process is a marathon, not a sprint. Deals often take 12–18 months, testing both stamina and conviction. Founders need to prepare mentally for uncertainty and deal fatigue.

Neal also shares how EquityX integrates employee ownership into acquisitions, why evergreen “buy and hold” models align better with long-term stability, and how upfront preparation — financially and operationally — can reduce risk while strengthening outcomes.

🎧 Tune in for an honest look at how to build exits that honor both your people and your legacy.

🎙️ Episode 15 is live! This time we sit down with Steve Little, CEO & Managing Director at Zero Limits Ventures, to talk about why every founder should start with the end in mind — and how to design a company that commands premium valuations.

If you’re building with an exit in sight — whether that’s acquisition, IPO, or succession — this episode is packed with insights on how to maximize enterprise value from day one.

What do we cover?

1. Buyers value different things — brand, IP, or customer acquisition might matter more depending on who’s at the table. Founders need to invest accordingly.

2. Complexity kills value — redundant systems, messy operations, and unclear positioning all drag down multiples. Clean, focused businesses are worth more.

3. Building to sell isn’t short-term — every business will change hands eventually. The earlier you structure to be “sellable,” the better your outcome.

4. Exit timelines are accelerating — AI and fast-moving markets mean exits can happen in 2–4 years, sometimes even under 18 months.

Steve also shares why readiness is the ultimate driver of better deals, and why founders who think like investors achieve the strongest exits.

🎧 Tune in for a masterclass on creating companies that don’t just survive — they exit strong.

🎙️ Episode 14 is live! This time we sit down with Kurt Winter and Kevin Salquist, co-founders of Big 7 Ventures, to talk about why essential industrial businesses remain the backbone of the economy — and how continuity-focused investing differs from traditional private equity.

If you’re a founder or owner thinking about succession, this episode offers a clear-eyed perspective on what really drives value in small and mid-market businesses.

What do we cover?
1. Resiliency reveals strength — businesses that weather downturns like 2008 or COVID prove competence and durability, and investors see that as validation.

2. Essential means irreplaceable — plumbing parts, industrial services, and other unseen products are critical no matter the cycle. AI can support operations, but it can’t replace infrastructure.

3. Exhaustion is often the trigger — most owners don’t sell due to lack of vision, but because they’re tired of day-to-day operations. The right partner lets them get back to creativity.

4. Pick partners, not just price — a slightly lower valuation can be worth it if it ensures your people, culture, and business continuity thrive post-sale.

Kurt and Kevin also share how they think about deal structures, culture preservation, and why clean, simple books matter more than polished banker decks.

🎧 Tune in for an operator’s view of continuity investing — and what it means for owners ready to transition without leaving their legacy behind.

🎙️ Episode 13 is live! This time we sit down with Brandon Duensing, CEO of Acquire Online, to talk about scaling remote-first businesses, breaking through plateaus, and why buy-and-hold models are an overlooked path to long-term value.

If you’re building a business that has grown past the early hustle and now faces the challenge of scaling, this episode is packed with lessons on how to structure for growth.

What do we cover?

1. Founders should be clear on their business goals — VC-style hypergrowth isn’t the only option. Buy-and-hold models can offer flexibility and long-term rewards.

2. Many small businesses stall at $3–5M in revenue or $1M in EBITDA — not because of the market, but due to lack of operational structure and leadership experience.

3. Founder-led sales eventually hit a ceiling. Building formal sales and operational systems is the only way to keep growth moving.

Brandon also shares how Acquire Online applies a “hospitality-first” mindset to scaling, why due diligence should double as an operational playbook, and how AI can amplify — not replace — the human touch in customer experience.

🎙️ Episode 12 is live! This time we sit down with Saydeah Howard, Co-Founder & Managing Partner at Cherryrock Capital, to talk about how founders should think about leadership, hiring, and scaling from Series A onward.

If you’re preparing to raise or building out your first leadership team, this episode is full of practical insights you can apply right away.

What do we cover?

1. Hiring mistakes made early can become culture and execution issues later — leadership structure needs to be intentional from the start.

2. Two of the most critical hires at Series A are the head of sales and the head of finance — both set the trajectory for growth and readiness for the next round.

3. Founders must move beyond inspiration alone — the best leaders empower, delegate, and adapt their style to get the best out of their teams.

Saydeah also shares her perspective on fractional executives, the importance of self-awareness in leadership, and how underrepresented founders can vet investors to find true partners.

🎧 Tune in for a candid look at what it takes to build the right team — and yourself — for long-term scale.

🎙️ Episode 11 is live! This time we sit down with Nuno Gonçalves Pedro, founder of Chameleon Venture Capital, to talk about what separates good founders from great ones — and what VCs should really be doing to support them.

If you’re raising at seed or Series A, this episode is packed with lessons on how to scale yourself as a founder while scaling your company.

What do we cover?

1. Know your gaps. Every founder has superpowers — but also blind spots. The best know what they bring and what they need to hire for.

2. Balance leadership and management. Inspiration alone isn’t enough; great 
founders also empower and delegate.

3. Cheerleader vs. coach. Most VCs are the former. A rare few act as true coaches — challenging and supporting founders through growth.

Nuno also shares his perspective on the state of venture capital, how too much capital can make founders lazy, and why self-awareness may be the most underrated founder trait of all.

🎧 Tune in for an unfiltered look at what it takes to grow into an A+ founder.

🎙️ Episode 10 is live! This time we sit down with Kristina Montague — Managing Partner at The JumpFund and Board Chair of the Angel Capital Association — to talk about what early-stage founders need to know before raising their first checks.

If you’re thinking about approaching angels or early-stage investors, this episode is full of practical, no-nonsense advice.

What do we cover?

1. Social media following is not enough. Investors want proof that people are paying for your product, not just following you online. Financial validation beats attention metrics every time.

2. Do your own diligence. Founders should vet investors too — by talking with portfolio companies and understanding their style, expectations, and value-add.

3. Tap into the growing ecosystem of women investors. Female-led funds and angel networks are stronger than ever, and they can provide a friendlier entry point for first-time founders.

Kristina also shares why preparation matters, how to think about traction at the angel stage, and how to avoid common myths about “easy money.”

🎧 Tune in for an inside look at how angels evaluate opportunities — and how founders can better prepare to win their support.