Reflecting on 2 Incredible Years in VC

Breaking in, finding a role, selecting a firm, and more

Hey there my friend 👋 , Justin here and welcome to Just Go Grind, a newsletter for the ambitious. Thank you to the 26 of you who joined since the last edition, if you aren't subscribed, and want to join 618 other subscribers, please subscribe below:

Today marks two years since joining VITALIZE Venture Capital as the Director of Marketing and Community.

It’s been an amazing opportunity to learn, meet lots of amazing people, and grow with a wonderful team.

During the last two years we’ve:

  • Launched an angel investing community that now has 425+ members

  • Put on in-person events in Los Angeles, New York, and Chicago

  • Invested millions of dollars into some remarkable startups

  • Grown the VITALIZE team to 7

Personally, I’ve met dozens, maybe hundreds, of founders and investors.

And I’ve been able to experience the boom of the industry in 2021 and its struggles in 2022.

I want to share a few takeaways from my experience so far with the hopes that it might be helpful for you as you think about your own career, even if that's not in VC or startups.

On entering the world of VC

There are many ways to get into the world of venture capital.

Mine was simple:

Okay but really, there is no predetermined way to get into the industry.

If you talk to 10 people about how they got into VC you might just get 10 different answers. For me, it happened to be a cold DM to Gale, combined with serendipitous timing.

Of course, before considering trying to break into the industry, whether as an investor or on the platform side like me, you’ll have to ask the all important question: Why?

Four of my reasons for getting into VC more broadly:

  • To bring the power of a strong network of founders and investors I built by hosting the Just Go Grind podcast to a VC firm

  • To learn more about the industry from the inside and contribute to improving it

  • To be around smart and ambitious people frequently

  • To participate in the financial upside of the industry

Am I happy I joined the industry?


Am I even happier that I joined the industry in my particular role?

For sure.

Let me explain.

On finding the perfect role in VC

Many people want a full-time investor role at a venture capital firm.

I think this stems from a few things:

  1. Wanting to get carry (A portion of the profits from investments) in their fund

  2. Wanting to make investment decisions

  3. Wanting to work closely with founders

These are all great.

But that wasn’t exactly my intention.

In my role, while I have carry in our fund and get to learn from founders, I’m also able to utilize my skills to grow what is essentially a startup within our firm, VITALIZE Angels, and build our brand more broadly. More on the platform side of venture here.

Reflecting on the past two years, the core of my role has remained the same, but it’s constantly evolving as we’ve brought on more team members, grown our audience, and built the foundation of our brand.

While early in my time at VITALIZE I spent my time getting VITALIZE Angels off the ground and planning our strategy for building our brand through content and community, now I’m focused on taking everything we’re doing to the next level. Which means my role will continue to evolve.

On selecting a VC firm to join

I mentioned a few of my reasons for getting into VC.

The biggest one?

The VITALIZE team itself.

I love the VITALIZE team.

I always look forward to seeing them - virtually or in person - and it’s because they’re genuinely good people, empathetic, work hard, and are just easy to be around.

When I was thinking about getting into VC, I wasn’t interested in joining a firm doing the same thing as everyone else.

I also wasn’t interested in joining a firm that looked like many of the other firms. After all, diverse teams perform better. We’ve seen this again and again.

But joining a VC firm isn’t just about the team, it’s also about the type of firm.

And there are many to choose from:

  • Early-stage vs. late-stage

  • Generalist vs. specialists

  • Small fund vs. large fund

  • Geographically-focused vs. not

  • B2B vs. consumer

The list goes on and on, with any number of combinations of those.

I chose to join VITALIZE, an early-stage VC firm with an angel community that invests in B2B software within the future of work, focused on U.S.-based companies from a small (<$100M) fund.

I’m glad I went this route.

It feels more like a startup, I have lots of autonomy, my skillset and network are much better aligned with an early-stage firm than a later-stage firm, and being part of a smaller firm gives me more of the upside (carry) than I’d have at a larger firm.

On building an angel investing community

Helping build VITALIZE Angels has been one of the hardest things I’ve done professionally.

When I joined VITALIZE, we had an idea of what we wanted to do - Create an angel investing community open to everyone - but no clue as to how we’d pull it off.

Typically, you have to be an accredited investor to invest in startups, with a requirement of having a net worth over $1 million, an annual income over $200,000, or meet some professional criteria.

If you wanted to join an angel investing group, you’d have to be an accredited investor, pay thousands of dollars in an annual membership, and invest a minimum of $5,000 or $10,000 per deal.

This is limiting to most people.

So we blew it up.

We created a unique model that leveraged crowdfunding, where you didn’t have to be an accredited investor, you could join with a reasonable membership fee, and you could invest as little as $1,000 into a deal.

For the last two years, I’ve thought about this community nearly every day.

First, it was figuring out this new model I just mentioned, which took months of research and dozens of discussions.

Next, it was coming up with a launch plan.

After that, it was making our first investment as a group.

And since then?


Both in the number of members and the number of investments.

It’s been a whole-team effort.

And while it’s been one of the hardest things I’ve worked on, it’s also been one of the most rewarding.

As the community has grown, we’ve been able to bring on Larissa Insogna to help us run it, we’ve hosted events, created educational content, and brought together amazing people from around the world, a mix of new and experienced investors.

And we built the foundation of something much bigger.

On the importance of building a brand

In VC, you want two things:

  1. Amazing dealflow (Being able to see amazing companies to invest in)

  2. Access to great deals (Being able to invest in those amazing companies)

How do you get these?

By building a great brand.

This is something I’ve thought about extensively and have been grinding on the past two years at VITALIZE.

Naval Ravikant, co-founder of AngelList, has a great quote about building a brand as an investor in his article on how to angel invest:

“As we discussed, the first way to build a brand is being a good investor to begin with. A second way is creating content that helps entrepreneurs. A third way is building infrastructure or platforms that help entrepreneurs.

Paul Graham can get into deals because of Y Combinator. Nivi and I often can get into deals because we started AngelList. Ryan Hoover can get into deals because he started Product Hunt. Platforms created by First Round Capital and Andreessen Horowitz help thom win deals against other VCs.

You can also start a conference. Jason Lemkin created the SaaStr conference; Tim O’Reilly at OATV publishes content and hosts conferences.

Steven Lurie is great at recruiting, so he started Team Builder Ventures. He put his value right in his brand name. Companies know what he offers; they know why they should give him a piece of the round and how he’s going to help them.”

At VITALIZE, our track record so far shows that our team is good at investing.

My focus has been on creating content and building community in the industry to further strengthen our brand.

I’ve created content geared towards actually helping founders and have been putting in the work to make us one of the most approachable VC firms.

I think this will help us be successful in the long run, with founders and investors wanting to work with us and us winning deals because of it.

Prior to joining VITALIZE, I knew building a brand was important, but in the last two years, I’ve thought more about this than in the previous years of my life combined.

On developing relationships

I've previously written about the value of building a world-class network.

At the early stages of VC where we invest, pre-seed & seed, this is especially true, as so much of this industry is about building relationships.

You’re building relationships with founders, co-investors, service providers, LPs (people who invest in venture funds), and in our case, current and future VITALIZE Angels members.

These take time to develop.

It’s all about playing the long game.

Through the Just Go Grind podcast and now The VITALIZE podcast, I’ve met hundreds of founders, potential co-investors, and future VITALIZE Angels members.

In the past two years, I’ve probably had hundreds of calls with people in the industry.

That’s the world of VC.

You’re always meeting new people.

Admittedly, while it’s fun, mentally stimulating, and you learn a lot, it can also be exhausting.

On the challenges of VC

It’s not all rainbows and butterflies in VC.

There is always too much to do.

There are endless emails, DMs, and messages.

You’re pretty much always on.

Companies shut down or struggle to grow.

And you have to say “no” constantly.

All of this is one big lesson in prioritizing.

I’d like to think I’ve gotten better at this in the last two years, always coming back to this question: What drives the most value for us at VITALIZE?

The answer isn’t always clear.

We're always experimenting.

And we constantly have more ideas.

So we have to focus.

And, as a small team, that’s perhaps the biggest challenge of all.

On what’s next

So, what’s next?

Taking everything to the next level.

Building a world-class venture capital firm and angel community that makes a big impact on the world.

Part of that includes a new challenge this year that I’m taking the lead on - hosting a summit for a few hundred people in Chicago in June, which you can stay up-to-date on here.

And who knows, in the years to come I may take on investing responsibilities in tandem with creating content and building our community. My role is always evolving.

What I do know for sure is I’m as excited as ever to continue building with this team.

Big things to come.

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