Boldstart's Fund Model and Check Strategy

Ed Sim has been a VC for 30 years. He's backed companies like Clay, Front, BigID, and Snyk. He writes What's Hot in Enterprise IT every single Saturday, 489 weeks in a row. And right now, he says this is the most exciting and terrifying moment he's ever seen in his career.

In this episode, Max and Ed break down what's actually happening inside startups and boards right now, why the old playbooks are dead, and what separates the companies that will survive this AI shift from the ones quietly getting killed by it.

Discussed in this episode

• Why engineering is no longer your bottleneck (and what is)

• The 5 P's Ed uses to evaluate every inception-stage investment

• The autonomous enterprise thesis and what it means for how companies are built

• Why AI-native leadership is now a survival reqxtuirement, not a nice to have

• The full Clay story: $600K to $100M ARR, how they stayed lean, and what actually unlocked growth

• The 3 CH's framework for being a great board partner to founders

• Why the best founders today are inside the AI jet stream, not chasing it

• What every board meeting sounds like right now

Episode highlights0:00 Intro & 

1:05 Episode Preview: Ed Sim & Key Takeaways

3:10 The Jet Stream Analogy: Two Types of Companies

5:43 How GTM Operators Should Evaluate Companies Like Angel Investors

7:20 The Collapsing of Moats & AI-Native Business Opportunities

10:00 Rebuilding Industries vs. Selling Software to Them

15:00 Why Old GTM Playbooks Are Dead

17:46 Ed Sim's Background: From Cutco to 30 Years in VC

21:43 The Five P's of Inception Investing

23:04 How to Evaluate Potential & TAM in a Fast-Changing Market

25:40 Staying Ahead of the Jet Stream as a Founder

26:32 The Autonomous Enterprise Thesis

28:44 Agent of the Week: How Companies Should Adopt AI Agents

29:10 How Agents Are Changing Engineering Bottlenecks

31:15 What Incumbents Must Do to Survive the AI Wave

32:53 Intercom, Snowflake & How Legacy Companies Are Adapting

36:43 The Clay Story: How They Found Their Footing

38:33 The Three C's of Working With Founders (Cheer, Challenge, Chill)

40:07 Clay's Growth Trajectory: $600K to $100M+ ARR

41:10 Clay's Agency GTM Model & Community Moat

43:50 Ed's Fund Model: $500K to $15M Checks at Inception

46:57 What's Hot in Enterprise IT & Venture Right Now

48:03 Closing Remarks

Key takeaways1. Engineering is no longer your bottleneck. Your people are. Code is shipping faster than your sales, marketing, and customers can absorb it. The constraint has flipped completely and most companies haven't noticed yet.

2. Painkillers beat vitamins every time. The only startups worth backing at inception are solving a hair-on-fire problem someone desperately needs fixed, not a nice-to-have they can live without.

3. The 3 CH's of being a great board partner. Know when to Cheer (when founders are getting beaten up), when to Challenge (when they feel invincible), and when to Chill (when they just need breathing room to figure it out). Elliot used all three with Clay to perfection.

4. If your CEO came from sales, you are in trouble. Surviving this AI shift requires product-driven, agent-native leadership at the top. The companies that adapted, Snowflake, Intercom, Atlassian, all changed leadership first.

5. The best founders are inside the AI jet stream, not chasing it. The question Ed asks every founder today: are you struggling to keep up, or are you the one constantly shipping and adapting faster than anyone can copy you?

Thank you to our sponsor

Connect with Ed: https://x.com/edsim  / edsim  Connect with Max: https://x.com/hackitmax  / maxaltschuler  Connect with Paul:https://x.com/PaulGTM  / paulsirving  

GTM Now is the media extension of GTM Fund, a venture capital firm investing in early-stage B2B companies. Every episode features the operators, investors, and founders defining what modern go-to-market looks like.GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/