OV New York City Meetup

Janine Sickmeyer
5 min readMar 10, 2022

The Overlooked Ventures team celebrated all eight of our portfolio companies in NYC at a swanky steakhouse with a long 15-person table full of oysters, champagne, and mini sliders.

Dinner with OV portfolio companies at STK in NYC

“When we get to be 300 portfolio companies, they’ll be having these dinners at Applebees”, joked Juan Medina, founder of Lalo, the first investment Overlooked Ventures made in August 2021. The table roared with laughter. “And then after one of us becomes a unicorn, we’ll be back here.” He continued as we all clapped.

Each founder raised their hands to announce who would be the first to IPO and who will be the first to get acquired.

After the first round of cocktails was delivered, we went around the table in order of investment so everyone could get to know the companies and founders in our OV family. Each founder pitched his/her company and shared a big upcoming announcement and the group followed up with cheering and clapping to celebrate the wins.

This is what founders need, especially historically-ignored founders who don’t have a network or connections.

This is what it looks like to have a supportive startup community.

This is what it looks like to feel a real sense of belonging.

This is what it looks like to bring together a diverse group of brilliant founders building billion-dollar businesses in untapped markets.

Overlooked Ventures General Partners and the first 8 portfolio company investments: CarpeDM, Femly, Lalo, The Difference, College Cash, Govalo, Moment AI, Blooming Health.

A Last Minute Trip, With a Lasting Impression

It all started just one week prior. I sent a text to my partner Brandon Brooks telling him we would get all of our portfolio companies together for one day and offer to cover their meals and a photoshoot but since we are a scrappy fund, we can’t cover their hotel or flights. Ironically, two of the portfolio companies were already in NYC that day and five more were only a train ride away. So we asked the one living in Seattle and he said “yes!” Immediately. We were thrilled.

Next, I checked with my favorite photographer, Megan Leigh Barnard, in Columbus Ohio, to see if she would come along for one day and do an impromptu photoshoot with no agenda or locations booked and she said “yes!” So it was ON! I wasn’t sure if our whole team could make it on such short notice but as soon as I asked Adam, Chauntelle, and Jaime to join, they got tickets and packed their bags.

24-hours in NYC and we made memories that will last a lifetime.

Founder of Govalo + OV | Femly + CarpeDM | Blooming Health + OV

More Than a Check

In less than one year, Brandon Brooks and I launched Overlooked Ventures, a $50M venture fund for historically ignored founders. We reviewed over 1,800 startup applications, and we selected 8 (so far) to invest in.

We are conviction investors who find non-consensus opportunities and high alpha and jump in with both feet.

We were the first check in for 6 of the 8 startups. The check sizes range from $100–500K and are often the largest checks for each of these companies and make a huge impact on their ability to grow.

But at Overlooked Ventures, we are more than a check, and the famous VC phrase: “How can we be helpful?”

Chauntelle Lewis (Inclusive Communities Manager), Adam Grant (Venture Analyst), Janine Sickmeyer (Founder and General Partner), Brandon Brooks (Founder and General Partner), Jaime Houssami (Head of Brand and Marketing)

Everyone on the team gets in the trenches with our founders and as former founders and operators ourselves, Brandon and I know that’s what it takes to make a successful company.

We set up meetings with founders to help them plot their next 100 customers, land the large partnership, or even use our development and design team to help them build a new website and pitch deck.

Here are just a few ways OV supports their portfolio companies:

  • Media relations (PR contacts)
  • Brand awareness
  • Review pitch deck for next round
  • Press pieces
  • Investor connections
  • Follow on checks
  • Marketing strategy meetings
  • Interviewing new hires
  • Monthly expert meetings
  • Community management strategy

The Overlooked Avengers

But it isn’t just about us, the GPs of the fund. It’s about the founders who said YES to us because, without them, the fund wouldn’t exist. They are the true heroes in this story. Demetrius Curry, founder of Overlooked Ventures #3 startup College Cash, looked around the table and said “You have formed the ‘Overlooked Avengers’ of startups. Just look at all of these inclusive and brilliant founders.”

As the dinner came to a close, we all raised our glasses and I began,

“Thank you all for saying yes. Thank you for allowing us to come on this journey with you. You should all be so proud of how far you’ve come, and this is just the beginning. Brandon and I, and the entire Overlooked Team, are honored to witness this moment in time and be a small piece of it all. To a lifetime of support and adventure!” 🥂

As we walked out the door and back to the hotel that night, a long time friend of mine who joined dinner looked at me and said:

“What you’re doing here is something you really have to see to believe. The founders, the companies they’re building, the team you’ve assembled. It’s incredible.”

And it sunk in. My dreams are coming true. 😭✨