Samir Rein and his wife, Ayanna Alexander Rein, founded Freedom Trail Capital in 2023 and aim to raise a $50 million fund.
Both are former Olympians, having competed in the triple jump for Haiti and Trinidad and Tobago, respectively, and now they're putting their grit and determination to work for founders looking to launch and scale consumer brands.
“I love people and I love connecting with people,” Alexander Laing told TechCrunch. “We know how to combine talent and business, and we know that athletes excel in these areas. But they also have the stamina to conquer things and organizations outside of sports.”
They, along with third general partner Ivan Lopez, have invested in seven startups to date, closing their first fund on a smaller scale, including Issa Rae's hair-care company Sienna Naturals, Kaley Cuoco's pet-supplies company Oh Norman!, Ciara's Ten to One Lamb, and Kudos, a diaper company backed by Mark Cuban and Gwyneth Paltrow.
Laing told TechCrunch that Freedom Trail Capital is continuing to raise funds, with seven more investments planned.
The Olympics and Beyond
Sameer Rane, co-founder of Freedom Trail Capital. Image courtesy of Freedom Trail Capital/
Laing knows what it's like to start and scale a company: He previously worked as SVP of Operations and Strategy at Westbrook, a venture founded by Will Smith and Jada Pinkett Smith, and has also worked with Jay-Z as Director of Operations at Roc Nation. Meanwhile, Alexander Laing is completing his PhD in Business Administration and will focus on health care financing and health disparities.
Layne knows what it's like to fail. In seventh grade, she joined the track team but failed the following year. As a high school senior, she decided to give track another go, this time focusing on the triple jump.
But it all worked out. Laing went on to Harvard, where he and his team set several records. He also became roommates with Mark Zuckerberg. They lived in a four-person dorm room during their freshman year, sharing a bunk bed. Laing said he may have been the 11th person to try out for Facebook. He also said he was quizzed on the show Cash Cab to see which Olympian was Zuckerberg's roommate.
“Mark has always been an architect, so of course we knew he would do something great,” Lane said.
Laing transferred to the University of Texas and was introduced to a new world of track and field. Many of her teammates were world junior champions, so the level was different. Laing competed at her first Pan American Games in 2007. She also participated in the Olympic tryouts in 2008, but missed out on the triple jump by just centimeters.
When he tried out for the Olympics again in 2012 and qualified, he was balancing his training with attending Georgetown Law School. Many people told him it was too much, but now when people ask him for advice he says, “Do what you can't do.”
“I thought if I could go to law school and juggle both, I'd get there,” Laing said. “At that point I was ranked seventh in the world in the triple jump. My goal in London was to give Haiti its first medal since 1928. I made it to the finals, but in the end I didn't win a medal.”
Layne and Alexander Layne competed professionally around the world for 10 years, where Layne learned from his teammates at the University of Texas how to make money from track and field, and where he was able to secure sponsorship and funding from the International Olympic Committee.
Working for Will Smith and Jay Z
Ayana Alexander Laing, co-founder of Freedom Trail Capital. Image courtesy of Freedom Trail Capital.
He then furthered his career in sports before moving to Roc Nation where he worked in entertainment and brand building. Laing worked with Jay-Z to build and expand his brand, including liquor, apparel, cannabis and book publishing divisions. He also managed platinum recording artists. He then moved to Westbrook to do similar work for Smith and Pinkett Smith. He worked there for four years before founding Freedom Trail Capital.
“While I haven't necessarily been allocating capital or investing, I have had a front-row seat to some of the investment decisions made by the Roc Nation fund,” Laing says. “Because I'm an executive at heart, I have a unique perspective on how to vet investment opportunities and how to support portfolio companies.”
Freedom Trail Capital's philosophy is to invest in talent-driven businesses, and he really knows what he's looking for: While Laing has helped Smith and Jay-Z achieve success with some of their brands, he's also seen a few cases where talent-driven brands didn't pan out as expected.
Now that he's on the other side as an investor, Lane said it's his job to protect and insure entrepreneurs, while also shielding limited partners from what appear to be bad investments.
“We look at the portfolio in a very different way than most people do because we're in a position to know what it takes for these brands to win,” Laing said.
Not every product has what it takes, he says. Freedom Trail Capital is, of course, looking for products with product-market fit. If there's a celebrity behind it, there has to be a good connection between that person and the product, and that person has to want to roll up their sleeves and get to work.
Lane said he has also worked with celebrities who wouldn't pose for photos or travel to Target to promote their products.
“We're not just talking about sponsorship deals anymore,” Laing says, “we're talking about you owning a significant part of the company. I've seen things fall through and really promising brands and companies fail as a result.”