25 Investments for 2025: A Follow-Up to the 2020 Series (Part 2)

TLDR: My syndicate is here.

In part 1 we talked about my investment criteria generally. Now we delve into the people who I would invest in (wether to start a company or of my time and energy to support) because they have an elite skill or perspective in some area.

Part 3 will have a list of companies I believe in, will be subscribers only.

People Investments

1. Corentin Villemeur – corentin.love

50 Cent started his book "Hustle Harder, Hustle Smarter" talking about Corentin's impact on his business. Corentin is a creative marketing director who spent 10 years building 50 Cent’s digital footprint. 50 Cent had glowing things to say about him in the book and as we all know, 50 doesn't always have glowing things to say about people. He's worked with Alesso, Shots Studios, Hoobe, so espescially if you are touching culture and influencers, his experience in blending culture with technology and commerce is key to brands that want to create lasting connections with consumers.

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2. Miro Zhelezov – Sales Leader at Intercom

Miro helped name and pivot LeadGenius, aiding companies like Zenefits during their fastest growth periods (of all time). His expertise in scaling sales processes is invaluable, and I see huge potential in his future endeavors.

3. Thompson Plyler – thompsonplyler.com

A charismatic full-stack developer obsessed with generative AI, Thompson’s unique background and passion make him one to watch. Whether he’s teaching at Flatiron School or building something new, his talent is undeniable.

4. Carleen Pan / Sheyla di Bona / Amanda Connell

These three are your ultimate 'get it done' chiefs of staff. They won't tell you what you want to hear—they’ll tell you what you need to know. If you're not ready for honesty, they aren't for you. But if you want real solutions, hire them now.

5. Esosa Ighodaro

Founder of Black Women Talk Tech and Accelerator Con, Esosa is one of my closest advisors. Her insight and community-building skills are unmatched. She’s constantly opening my eyes to new markets and perspectives.

6. Tim Falls

The community leader behind the success of both Sendgrid and DigitalOcean, Tim understands how to build developer communities in a way that propels companies to new heights. This is where many startups fail—Tim knows how to make them succeed.

7. Delyn Simons

Product marketer with a focus on developer experience, she help build ecosystem marketing teams at Atlassian, Shopify, and Mashery. If you liked this talk, she is responsible.

8. Blaga Lund

VP of engineering at 2 acquired companies (Kustomer, Voyat), Blaga is sharp and down to earth. Unicorn.

9. Chris iExcel Rodriguez

B2B marketing guru, building out an agency that is getting great results for clients. Most loyal guy around and has the patience only a girl dad of 3 could possess.

10. Annie Maguire

Conversion copywriter, Annie is the one that taught me how to write copy, and how to conduct customer interviews. Has done brand work as well but sweet spot is early stage startups that need to fix their messaging (most don't realize their copy is losing them sales, not their product).

11. Willow Hill

Best brand marketer I've worked with, learned a great deal about the methodology of her work at Airbnb and Redbull as well as her work supporting my mother's Joy With Paper. Her agency Scout Lab should be in your top list.

12. Eric Matzner

Innovation comes from people taking new approaches to things and transferring concepts across industries. Eric has always been working on world changing projects, and even though he may not fit your prototypical mold, the first principles thinking is there to make change. I expect a Nobel prize at some point.

13. Zoya Lehrer

The only person on this list who I have never spoken to. Her mastery of content, product positioning, and social, are the key elements of helping businesses grow in this new content age. Very relatable and authentic, with a product that makes sense for parents.