We recently connected with Matt Williams and have shared our conversation below.

Matt, thanks for taking the time to share your stories with us today How did you come up with the idea for your business?

I originally came up with the idea for Approachable in October of 2020. Ironically, despite living through unprecedented isolation and social distancing, my inspiration had nothing to do with the Covid-19 pandemic itself.

I’d been experiencing a sort of social flatline for quite some time, even before the pandemic hit. You know how it goes—you try to get your friends together for a spontaneous drink on a Tuesday night after work, and suddenly it feels like everyone needs a week’s notice. Even though I understood that everyone had their own responsibilities and commitments, it was still a let down. I missed the thrill of those spontaneous moments I used to enjoy back in college. Especially now that they had seemed to be replaced with me spending most nights at home alone, when I wanted to be out.

So, in an attempt to recapture that spark, I started experimenting. I would venture out alone, heading to places and events I wanted to go to, hoping to meet new people along the way. Picture this: I’d sometimes dress up, maybe sit at the bar to eat/work, trying my best to look approachable (no pun intended), and hope that fate would bring someone my way. But being an introvert, as much as I wanted to strike up conversations, I found myself waiting for others to break the ice first. And as you can imagine, most nights ended without any meaningful connections made.

Fast-forward to when Covid-19 restrictions were lifted, I was determined to create a social life like the ones you see on TV shows like “Friends” or “New Girl.” So, I took a leap, sold all of my things, and moved to Chicago (from my hometown of Detroit), where I didn’t know anyone at all. To give it my best shot, I even moved into this co-living community for young professionals which was basically an adult version of a dorm, where you get paired with 3 other roommates. It felt like a fresh start, and a chance to rewrite the script of my social life.

But let me tell you, even with all those changes, it was still a challenge. It felt like I was constantly putting in so much effort to meet people and break free from that sense of “missing out” when I would go places solo and see others grouped with their friends. And then, one evening, I had a realization. It was Halloween, and as I walked to the grocery store, I couldn’t help but notice everyone in their costumes, ready to go out and have a blast. It hit me hard—I felt like I was missing out on so much fun, being so close to others who were enjoying themselves while I was left out. And that’s when it hit me: there must be thousands of people out there, just like me, who had recently moved to the city, knew nobody, and had nothing to do that night. We were all craving connection, and if only we knew each other existed, we’d jump at the chance to meet up and share those experiences together.
And that’s how the idea for Approachable was born. I had this lightbulb moment, thinking, “What if there was a way for approachable people, who were compatible and interested in doing the same things at the same time, to just know about each other’s existence and spontaneously meet up?” It was like a burst of inspiration, and I could feel the excitement bubbling up inside me.

The more I thought about it, the more it made sense. I realized I was onto something unique, something that nobody else was offering. It was all about creating a platform that leveraged technology to connect like-minded individuals, helping them discover each other and embark on spontaneous adventures.

Matt, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Hey there! I’m Matt Williams, a serial entrepreneur with almost a decade of experience in product management. From the very start of my professional journey, I’ve been passionate about using technology to solve real-world problems for both consumers and businesses. Alongside my entrepreneurial ventures, I’ve also had the opportunity to lead product teams at renowned companies like PayPal, Carhartt, and Ford.

I was born and raised in Detroit, Michigan and ever since I was a kid I’ve been fascinated by business (I even used to carry a briefcase and business cards to elementary school.) I caught the entrepreneurial bug very early and as a kid did everything from selling lemonade and tutoring, to asking for a lawn mower for my 13th birthday so that I could start a lawn care company. However, my true journey as a startup founder didn’t begin until I was in grad school pursuing my MBA when I launched my very first tech product. At the time I was not very tech savvy at all and wouldn’t even have been able to tell you what an API was. However, fast forward a few years, a couple ventures, and plenty of valuable life lessons later, I am now the founder of Approachable, where we are solving the problem of adult loneliness and redefining what it means for a social platform to facilitate meaningful human connections.

We’re living in a world where loneliness has reached epidemic levels, with health experts even comparing its effects to smoking and obesity. Additionally, loneliness is particularly affecting younger generations. Studies by Cigna reveal that a whopping 79% of Gen Z and 71% of Millennials feel lonely due to a lack of meaningful in-person social interactions. When you consider other studies, like those conducted by OnePoll and Evite, which suggest that the average American hasn’t made a new friend in five years, or those by Flash Pack revealing that adults in their 20s and 30s miss out on 26-34 experiences per year due to a fear of going solo, you begin to see the seriousness of the problem we’re addressing. Adults everywhere are struggling to find social companions and share meaningful interactions, often resorting to searching “Where to Meet People?” on Google.

So, how does Approachable tackle this problem? We’ve created a unique platform that empowers users to find social companions for any experience they don’t want to face alone, on demand. Let’s say you’re itching to explore the city, see that art exhibit, or try a new restaurant, but your friends are busy, aren’t interested, or don’t live nearby. Instead of letting the idea of going alone hold you back, you can simply share your plans on Approachable and we’ll do the rest by connecting you with compatible individuals who are eager to join you – right here, right now. It’s all about connecting people and allowing them to experience life together in a way that’s fulfilling and meaningful, for the type of on-demand, offline interactions that you can’t Google.

What sets Approachable apart is our fresh take on social networking. We’re not about superficially matching you with random “friends nearby” or mindlessly swiping on faces. Instead, we’ve flipped the script to make it more purposeful and exciting. On our platform, it’s all about searching for impromptu adventures and experiences that genuinely interest you, not just looking for generic “friends.” We’ve also designed Approachable to prioritize compatibility. So when you find an experience that catches your eye, we consider how well-matched you are with the person who posted it. No more wasting time on countless conversations that go nowhere. We’re here to make sure your social connections have real potential and lead to meaningful interactions that go beyond the screen.

We’re still early, but I’m extremely proud and excited about where our team is headed, and the inclusive community we’ve built so far. So if you’re reading this and looking to reignite your social life, make genuine connections, and embark on new adventures with like minded individuals, join us on this journey!

Have you ever had to pivot?

The current version of Approachable is actually the result of a pivot. At the start, our team set out with the idea of targeting conferences as our primary market. We believed conferences would serve as the perfect launching pad for us since they already brought together a concentrated crowd of hundreds to thousands of people seeking to optimize their offline connections and networking opportunities. On top of that, we hypothesized that conference organizers would be willing to pay us to enhance the quality of connections among these attendees.

However, as we immersed ourselves in interviews with conference organizers, attendees, and exhibitors, we uncovered a fascinating, and at the time – discouraging – revelation. The only ones who truly cared about the quality of networking between the attendees, were the attendees themselves! The organizers primarily focused their efforts on connecting exhibitors and sponsors with attendees to facilitate business transactions. Their priority was showcasing a high return on investment for exhibitors from the connections they facilitated, and using that data to sell more booths for future conferences.

So right away we realized that conferences weren’t going to work in the way that we imagined, unless we built a bunch of event app features on top of our original concept. Instead we chose to pivot towards a direct-to-consumer approach to avoid diluting our vision, and remain focused on the problem. Although, to be honest, even though I knew pivoting was the right choice, I had initial reservations about building a social network from scratch and tackling the cold start problem. Conferences appeared to be a less intimidating entry point. But I once heard that the primary job of the CEO of an early stage company (outside of making sure you don’t run out of runway) is hiring a great team. While I had confidence in my ability to build products, and to build a community to a small degree, I recognized the importance of finding a teammate who excelled in community-building to truly bring our vision to life.

As luck would have it, I stumbled upon a remarkable teammate who shared our passion for solving the human connection problem. Together, we hit the ground running, and within just a few months, we have successfully established one of the largest and most active social communities in Chicago. This pivot taught us invaluable lessons in adapting to new realities, and accepting that as a leader you don’t need to be the best at everything your company does. Instead you just need to find the best people, who share in your vision.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Since becoming a founder, I’ve had to challenge many conventional “wisdoms” and unlearn certain ingrained behaviors. One of the biggest lessons I’ve learned is to stop seeking someone’s blessing before taking action. Society, whether it’s in school or the workplace, often conditions us to constantly seek approval at every step. We find ourselves asking our bosses, going through executive reviews, and facing various committees just to get the green light for a decision. But when you’re starting a company, especially in the early stages, it’s a different story. It’s just you, and sometimes imposter syndrome creeps in because there’s no one telling you if you’re doing things right—I’ve definitely experienced that. However, what’s truly empowering is navigating through the highs and lows, gaining a deep understanding of the industry, and realizing that no one really has all the answers. Everyone is working with hypotheses, some based on extensive data and others on pure product intuition. Through this process, I’ve come to a point where I trust myself more. I’ve learned to rely on my own judgment and instincts.
Letting go of the need for external validation has been liberating. It means taking ownership of my decisions and embracing the uncertainties that come with being an entrepreneur. It’s about being comfortable with the fact that sometimes there’s no clear right or wrong answer. By unlearning the habit of seeking the blessings of others, I’ve discovered the importance of trusting myself and my abilities.

Contact Info:

• Website: https://www.approachable.ai/
• Instagram: https://instagram.com/approachable_app?igshid=MzRlODBiNWFlZA==
• Linkedin: https://www.linkedin.com/in/mattwilliamsmba/