In this episode, we’re joined by Chris Tottman from Notion Capital. Before becoming a VC, Chris co-founded MessageLabs and helped grow it into a $700 million exit, so he’s seen the startup journey from both sides of the table.

We talk about what really happens when your product-market fit starts to slip—and why it quietly wrecks your entire go-to-market strategy. Sales start missing targets. Marketing can’t get traction. Churn creeps up. But most teams keep pushing forward without realizing the core problem is the product just doesn’t fit anymore.

• (00:00) - Introduction
• (09:55) - Common mistakes in Go-To-Market strategies
• (19:54) - Identifying a VC case
• (30:05) - Importance of Product Market Fit
• (39:38) - Transitioning from VC to PE
• (50:07) - Next week: pricing changes

Not all consultants are worth it. Some drive real impact. Others just burn your time and budget.

In this episode, Toni and Raul dive into how to tell the difference. They break down when it actually makes sense to bring in outside help, how to vet someone properly, and the biggest red flags to avoid.

You'll learn why consulting is a real skill, what good execution support looks like, and how to think about pricing and value.

• (00:00) - Introduction
• (02:48) - Do you actually need consultants?
• (05:22) - The consulting relationship with startups
• (08:29) - Identifying red flags
• (10:41) - The hammer people
• (16:17) - Consulting is a skill
• (21:14) - Consultants as challengers
• (24:40) - Pricing and value in consulting
• (30:06) - Execution and enablement
• (33:38) - Summary
• (35:45) - Next week: Chris Tottman on VCs

In a world of AI-generated noise and automated outreach, Cliff Simon has built a multi-million dollar business by doing something simple but rare: showing up in person.

In this episode, Cliff shares how he turned events, community dinners, and authentic relationships into a powerful go-to-market strategy. He breaks down why most event-based approaches fail, what it really means to play the long game, and how founders and revenue leaders can drive growth without relying on cold outreach.

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• (00:00) - Introduction
• (01:53) - The Importance of In-Person
• (06:01) - The Role of Pavilion
• (08:08) - Building Relationships
• (12:09) - Building for Long Term
• (16:41) - Modern Networking Tactics
• (21:58) - Evaluating Event Success
• (24:57) - Common Misconceptions in Event Strategy
• (26:34) - Effective Event Strategies
• (31:39) - The Power of Personal Branding
• (32:13) - Comparing Rev Ops Events
• (36:28) - Next Week: What You Need to Know About Consultants