S2E11: Earned Insight, Not Outsourced GTM – Dakota McKenzie on Backing Founders Who Lead

Dakota McKenzie was the first in his family to go to college, and figured out his path into tech by working at startups in Boston to pay for school and becoming obsessed with working in the earliest stages.

That led Dakota into early GTM roles at Databricks and Segment, then he joined Unusual Ventures under John Vrionis. In parallel, he started Dynamic Growth Partners with his co-founder Trey, helping technical SaaS founders find product-market fit and build GTM. That business now supports over 60 companies doing $160M+ in combined ARR, and brings in $2M/year. Over 30% of their clients have gone on to raise Series A from top-tier firms.

“I started noticing that many startups just don’t make it — even the ones that look good on paper,” Dakota says. “There wasn’t some big aha moment. It was just the same patterns showing up over and over.”

He’s now building Dynamic Fund, a $10M fund writing $500k–$1M checks. He’s made four investments to date including:

* Infisical (which recently announced its Series A round)

* Flightcrew

* Judgement Labs

* Gist

“Good consulting isn’t good investing,” he says. Only one of his 60+ clients has become a portfolio company. He keeps the lanes separate, and that separation is intentional.

He also doesn’t promise to do the work for founders he invests in, “If a founder's picking me because I have to do a bunch of legwork to save them or build the business. I think the issue with a lot of GTM operator firms is the founder's like, oh thank God, I never have to think about this.The best founders just want to be elite, be coached, and then they want you to get out of their way.”

In terms of the founder’s he’s backing, He’s looking for technical founders with obsessive curiosity, self-awareness, and the willingness to do what it takes.

“Someone with high conviction in themselves and real technical acumen can always figure it out if they also have the willingness to build a business. They don’t need to be a CRO. But they do need to show up to events, talk to customers, figure out what’s actually happening.”

Grit is table stakes… he digs deeper:

“When this person is at their absolute lowest, what are they going to do about it? Startups are hard. We’ve seen this even on the consulting side, some people are just ready to give up. We want technologists who believe in themselves and will do whatever it takes. Not just proud engineers but real CEOs.”

Dakota leans into the lens as an investor that he’s build from doing the work at depth again and again:

“You’ll hear everyone say you need to get to $1M in revenue as fast as possible. Happens all the time. Now it's, well Cursor hit $200M in 18 months — why haven’t you? But that spectrum is so wide. What’s more useful is asking: Do we even have the right product? Do people actually want this? Why is this differentiated? Then you can build a repeatable process from there.”

Special thank you to Walter for introducing us to Dakota 🙏