Meaningful Relationships in a Startup Ecosystem in Just Six Months - A How-to with Anj Fayemi of Rivet

The Rivet team with their 2023 1871 Industry Disruptor Momentum Award

Earlier this summer, while doing some mindless scrolling, I noticed a tweet comparing breaking into the Chicago startup ecosystem to enduring the city’s winter: rough and behind closed doors. I’ve been thinking about this for months now - working in Chicago’s startup scene for the better half of a decade, it personally feels like we’re back to being overwhelmed with ways to plug in, my email inbox flooded with happy hours, panels, pitch competitions, and summits. But are these meaningful ways to connect and if so, how do we leverage them to develop mutually-beneficial relationships?

In April, I met Anj Fayemi, CEO & Co-Founder of Rivet. Anj was fresh off the plane from Boston (literally, he had texted me a picture from the airport), a new transplant to Chicago with his co-founders, Simran Pabla and Nafim Rahman. Anj started Rivet, an AI-powered platform that helps artists and their managers operate more like small businesses, at the Massachusetts Institute of Technology in 2020. Later bringing on Simran and Nafim, the team operated for some time in Boston, including participating in a Techstars cohort there, before raising their pre-seed round. They knew they had to move to another city with a deeper creative economy, considering Atlanta, Los Angeles, New York City, and Chicago. Inspired by the success of Chicago-born startups focused on music and entertainment, including Cameo, Trala, Songsleuth, and Songfinch, and boosted by a Drive Capital investment, they packed their bags for the Midwest.

In just six months, the Rivet team has built a meaningful presence in Chicago’s startup community, including features in Chicago Inno and recognition in the 2023 1871 Momentum Awards as winner of the Industry Disrupter category. Impressed with how quickly the Rivet team has made a home for themselves in the “wintery” ecosystem of Chicago, I reached out to Anj to get his advice for transplants, first-time founders, or those generally feeling a little isolated from the startup scene.

Build Out Your Initial Network

For Anj, participating in startup programming at MIT and in Boston (Techstars, AllRaise, etc.) equipped him with a network of founders and mentors willing to share their thoughts on who would be most helpful to pay attention to in Chicago, whether through social media or attending events they may be speaking at. Certain names, like Gale Wilkinson of VITALIZE, came up over and over and Anj started to write out a list (literally) of people he knew he had to meet as Chicago became more of a reality for their team.

Helen Adeosun, CEO of CareAcademy, gave me the advice that I should always be asking if there are any other people, whether they are Techstars founders, Black founders, founders in my industry, or programs I should know. Understand who are the superconnectors in your city or industry.” We talked about people like Landon Campbell (Drive Capital), Claude Cimeus (P33), and Abin Kuriakose (World Business Chicago), with Anj elaborating, “If you meet them, they will introduce you to the right people. Let them know what you are working on and extend that to the next layer of everyone you meet - here’s who we want to meet with and what we want to accomplish.”

Making the Ask

Anj’s list included some heavy hitters and some of these individuals were more accessible than others. He was laser-focused on pitching Gale and VITALIZE, something any founder can apply to do on their website. Declined for investment by VITALIZE, but with deep admiration for Gale’s work, he put her on Rivet’s monthly updates and let her know they were moving to Chicago. This led to an invitation to a small dinner that VITALIZE was curating. He made strong initial connections at that event and emailed everyone following to set up another time to chat. “This led to eight solid, new Chicago contacts for me,” says Anj.

Anj’s real “must-meet” list he started when he knew he’d be moving to Chicago.

Another Techstars Boston friend, Derek Canton, had recommended applying for Future Founders, a Chicago-based non-profit focused on supporting young, diverse entrepreneurs. Through Future Founders, Anj met Mel Steinbach, Chief People Officer at Masterclass, formerly in the same role at Cameo (and a LongJump LP!). Mel proved to be a valuable industry contact for Rivet but also introduced Anj to her daughter’s best friend, a fellow Nigerian (Anj was raised in Lagos), who became his first solid Chicago friend outside of startups. Not all of Anj’s introductions came warm - he sent cold messages to people he wanted to get to know, even resorting to flattery to stand out. Over LinkedIn, he reached out to Boyede Sobitan, founder of OjaExpress, sending along a picture of his must-meet list in Chicago. Anj excels at this personalized touch, which extends to how he meets. He encourages other founders to try to make in-person connections, whether it’s for coffee or a drink, it allows you to get to know your contact more personally versus the run-of-the-mill Zoom.

Keeping Your Relationships Warm: Give First and Stay Present

Identifying and getting some of those initial meetings on the calendar is just the first step in building out your startup community. Maintaining those connections is where relationships become meaningful. One of Anj’s superpowers is enthusiastic recognition: he’s a cheerleader and proponent of those around him, boosting their stories of success or simply shouting them out for their wins. This comes from a genuine place, he says he loves to pump people up, but also it is a low-lift way to show someone you’re on their team. “If someone pops into my mind at night or I hear a song or watch a video that reminds me of them, I’m going to text them to let them know,” he says. Further, he recommends to other people that they articulate to him, what their specific needs and challenges are so he can keep them top of mind when he’s in other conversations and potentially make introductions that can help them. “Asking is part of being a founder. You can get more comfortable asking if you first get comfortable giving,” he says.

In addition to his personal efforts, the Rivet team maintains a steady presence through social media and other online networks they are a part of. He recommends that founders engage with the people they meet on the channels most relevant to them and consistently put out content. For Rivet, that meant including everyone (investors, colleagues, friends, family) on monthly updates and getting more active on LinkedIn, “Our content has helped create brand recognition. I never used to [post on LinkedIn] prior. At first, it was annoying, but it’s muscle memory now. It’s a low-touch way for people to see you around,” Anj says. When asked if this has paid off for them, he talks about performing to a packed house, filled with everyone he’s been meeting over the past few months, at Rivet’s first #FanarchyFriday event in August.

Not All Events are Created Equal - Protect Your Time

Going back to my initial question of if Chicago’s ecosystem is really that icy to break into and whether events are meaningful, I asked Anj how he initially found events and if he felt he wasted his time on anything when he first moved to Chicago. His recommendation was to know what you’re looking for - if you are coming in blind, without any context, large speaker events and panels are a good way to educate yourself, but you’ll quickly find those gatherings can be hard to make meaningful connections from. As soon as possible, his advice is to get into more “dynamic” gatherings, “Prioritize small group settings where the purpose is meeting new people, rather than hearing someone talk,” he says.


As demonstrated by Anj’s story, it's possible to find warmth and build a meaningful presence within any startup community, and especially Chicago. The key, as he suggests, lies in building out your initial network diligently, making the ask by reaching out to key individuals, and keeping relationships warm through genuine support and collaboration. While Chicago's startup scene can appear daunting with its plethora of events and opportunities, it's essential to be discerning in how you invest your time, focusing on smaller, dynamic gatherings that prioritize meaningful connections over passive learning. Ultimately, with the right approach and a commitment to giving and receiving within the ecosystem, founders can thrive wherever they are planted.

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