Staging environment
Free Lesson

How to think in bets for GTM

Part of Building an AI GTM Engine

Hosted by Michael Slawson and Ben Holley

Wed, Sep 30, 2026

4:00 PM UTC (1 hour)

Virtual (Zoom)

Free to join

168 students

Invite your network

What you'll learn

Absorb the fundamental principles of bets based thinking

Learn how to ideate, right-size, and prioritize all of the things you can do into the things you should do.

Design a weekly/monthly business review to manage your bets

See patterns on how businesses manage complexity and share context to ensure they are moving as quickly as possible.

Look at best practice GTM bets that other companies make

Do pattern-matching from dozens of bet portfolios that we have created from working with our clients.

Why this topic matters

The surface area of GTM is wide and unwieldy. It is hard to know where to start, if you are executing well, when to stop a specific initiative, and whether there are higher leverage areas for your scarce resources and time. Bets-based thinking in GTM lets you organize all that you can be doing and have a mechanism for iterating, stopping, or scaling the things that you are working on, and makes your GTM motion inspectable and faster-moving.

You'll learn from

Michael Slawson

Built and sold a 7-figure agency, GTM @ Clipboard Health, Hum Capital, Deloitte

I build revenue engines for venture- and PE-backed B2B companies: diagnosis, systems, and execution. I built my agency from zero to $1M in revenue, completing 50 engagements in under two years with no employees and a few excellent GTM engineers. Then I sold it.

I have a wide range of B2B and finance experience, including:

  • Grew Clipboard Health's hospital and health systems vertical by 5x over 18 months, into the company's second-largest revenue line.

  • At Hum Capital, originated 40% of company revenue across ~2,000 direct conversations with founders and executives seeking non-dilutive capital.

  • At Deloitte Advisory, I underwrote $2.6B of debt financing across five major U.S. infrastructure projects.

Versed in a wide range of GTM tooling and systems.

Ben Holley

10+ GTM systems in production, GTM @ Apero, AirOps, Cyft, Clay, Lightyear

I build the systems that run go-to-market: signal automations, cold email infrastructure, attribution, and AI workflows. At AirOps I influenced $1.7M in pipeline in a single quarter and generated $700K from one lead magnet in a matter of weeks. I have 10+ systems in production, and all of them live in a repo.

I have a wide range of B2B GTM and engineering experience, including:

  • Employee #2 at Cyft, where I helped the team raise $5M from Base10 and built the outbound and channel partner program from scratch.

  • Booked meetings with 1% of the Fortune 500 at Lightyear, finishing #1 in outbound accepted meetings for H1 '24 on an enterprise motion I built from the ground up.

  • $1.6M in pipeline in one quarter as an SDR at PandaDoc, ranking #1 on a 10-person team and then #1 across a 50-person sales org.

See all products from Michael

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