100 coffee meetings: A guide to more meaningful, purposeful networking

Building a network is one of the most essential — and sometimes overwhelming — aspects of starting and growing your business. Like other scrappy founders before you, if you’re eager and hungry for knowledge, you’ve probably already found yourself in the midst of what seems like hundreds of coffee meetups, happy hours, or, more recently, Zoom meetings and phone calls.

From making time to learn from those who have been in your position, to connecting with other founders and potential investors, to even listening to your target customers describe their pain points — it can be tough to balance all the input coming from various sources at once. It’s an exhausting process even for the most curious and extroverted founders among us.

But the process of building those relationships matters in a big way at every stage of growth. Not only does networking account for 85% of hiring, but it’s also key to crystallizing your mission, honing your pitch, and eventually finding values-aligned investors and customers. Plus, if you do it intentionally and stay true to yourself in the process, you’ll inevitably form some of the most meaningful connections in your life and career.

Five tips for deeper, more productive networking

The first rule of networking? Don’t think of it as “networking.” (And the second rule is that there are no “rules.”) While there’s no surefire formula for networking, here are a few principles to keep top of mind.

1. Don’t just make connections — build a community

Let’s quickly address the elephant in the room (or...article) — the term “networking” might not necessarily evoke excitement at first read. For some, the term’s been co-opted by scenes of people milling around a bar wearing name tags, making cringeworthy small talk, or collecting business cards that will be tucked into a drawer for the next one to 100 years.

But that’s not what purposeful networking is about. It might help to reframe it as building a community for yourself and your business to be part of.

As James Chapman, the founder and CEO of networking app Plain Sight, told us in an interview: “Networking has largely been thought of as awkward and random, and usually a big waste of time. But community is different. It’s about forming bonds with like-minded people you can build and grow with.”

James formerly owned a coworking space in Chattanooga, Tennessee called Workaholics, where new founders and creatives could congregate from 6 p.m. to midnight to work on their side projects and business ideas outside of their full-time day jobs.

Witnessing the sense of community and seamless collaboration among Workaholics regulars is what inspired Chapman, alongside co-founders Alex Johnston and Alexis Matteson, to launch Plain Sight — a networking platform (and recent Apple App of the Day) that aims to make business connections more intentional.

The guiding philosophy behind Plain Sight is a good one: Networking should be mutually beneficial for both parties and focused on building a community of mission-aligned peers. In other words, when you’re building a business and growing a network, values matter.

Like James saw at Workaholics, building a community doesn’t just mean reaching out to seasoned mentors, potential customers, or future investors. For many founders, their greatest source of support is other founders, especially if they belong to an underrepresented group in an otherwise white, male-dominated space.

Whether you join a founder community or an industry-specific group, openly sharing your own resources and experiences can help build trust and respect among you and other members.

“It helps with loneliness,” James said. “Sometimes you need to just say: ‘I’m a founder, you’re a founder, and we’re figuring it out.’ We need a safe space to be vulnerable, inspired, and encouraged.”

2. Lean into vulnerability: Asking for help is good for business

It’s no secret that most successful entrepreneurs have gotten a little bit (or more often, a lot) of help and advice from more experienced founders and business leaders.

You might worry that investors, potential mentors in your industry, or founders who are a few steps ahead don’t have time to meet with founders of earlier stage companies. And some won’t. But most of the time, you’ll be met with a positive response, because it’s flattering to be asked for advice, and it feels good to do good.

If you identify a person who you think might be able to offer some insight from their own experiences — someone whose values align with your own — there are some things you can do to build a meaningful relationship and make the conversation worthwhile for them, too.

At the start, try to make your questions as specific as possible. You likely won’t get the answer you’re looking for by asking big, sweeping, general questions or sending a vague note that “any advice would help!” If you can do enough research on the person’s background to know their areas of expertise, you’ll be better able to ask more specific questions for them to weigh in on.

And, rather than asking how you should do something, ask how they did something. That way, you’ll learn from someone else’s experience rather than asking for prescriptive advice that might not match up with your exact situation.

It also helps to make it as easy as possible for them to get involved. If you’re reaching out via email or LinkedIn, give enough background info that they understand the core of your ask. Use tools like Calendly for seamless scheduling to limit back-and-forth. Be flexible about timing and offer the option to meet virtually or in person if it’s applicable.

Something else to keep in mind: While there are lessons to be learned from founders across industries, connecting with others who are building in the same space as you is a good place to start.

When Dulma Altan founded her first company, an all-natural fragrance line called Potion, she had trouble finding the right resources to help her through the process. She began connecting with other woman-identifying ecommerce founders to learn everything from supply chain details to what goes in an investor pitch deck.

From there, she founded Makelane — a platform for female founders to connect, share, and enroll in courses while growing their businesses. “What's really helpful when you're starting any kind of business is talking to people in your vertical,” Dulma said. “So now that I'm in Ed Tech, it's really been helpful for me to talk to other founders who are building startups around community, education, and online learning.”

Initially, a values-aligned peer or mentor with experience in your industry might help you figure out how to grow your business, but eventually, over time, those same meaningful relationships can lead to finding the right investors, making better growth and hiring decisions, understanding your customer base, and more. It all starts with one (specific) ask for advice.

3. Define your mission early, because some advice won’t match up later

In his guide to raising venture capital, Andy Sparks writes: “Learning when to listen to the advice of VCs and other entrepreneurs and when to listen to your instincts is an essential skill to develop; it can be the best thing you do at the start of your company.”

If you start with a solid mission and business purpose, you know how to pitch it, and you believe it yourself, it will be exponentially easier to manage the barrage of feedback, points of view, and (at times) rejection that’s inevitable while networking.

You’ll run into folks who don’t “get it” when it comes to your vision, and that’s OK. If you’ve done the legwork early on, you’ll be better able to determine when to trust your own gut and when to pivot based on feedback.

Forge relationships with people who will support and challenge you to get where you want to be, and do the same for them in return. The more authentic you are upfront, the easier it will be to steer clear of those who aren’t in sync with the way you want to represent and grow your business.

4. Make yourself approachable by doing the things you like

There’s a very simple trick to growing your network authentically and finding people with whom you’ll feel most at ease: Do things you like doing, go places you like going, and put yourself in situations that feel comfortable and right for you.

This philosophy helped launch an entire career for U.S. Army veteran David Gowel, the CEO of RallyPoint, a social and professional networking community that aims to support veterans as they transition to civilian life and careers.

When David himself was transitioning out of active duty and in the process of founding his first company in Boston, he felt uncomfortable and out of place at many of the traditional “networking” activities and events in the area. So he found a gym in the area and started working out — and didn’t wear headphones, to avoid seeming closed off to a conversation.

“I made so many initial connections by doing something that I liked, and by making myself approachable,” David said. “From that one gym alone, I met investors, customers, partners, future employees — just by doing something I felt comfortable doing.”

Whether it’s a gym like the one David found, a coworking space like James Chapman’s Workaholics, or an online community like Makelane, connecting with like-minded peers inevitably leads to stronger connections and a greater chance of getting real value out of a conversation.

Ultimately, people will believe and invest in people and teams more than products or business ideas. If someone identifies with you on a deeper level, they’ll stick with you as you grow.

5. Prioritize the quality of your relationships over the quantity of your network

Growing your network and building relationships is important, but that doesn’t mean it has to be done with a sense of urgency. If you take time to be intentional about who you reach out to and how you go about it, the bonds you form will be more meaningful.

Don’t set goals for how many conversations you want to have in a given timeframe; set goals for the types of conversations you want to have and what you hope to learn.

And finally, pay it forward! The best way to build an authentic community while you’re building your business is to be an active member of that community yourself. No matter what your level of experience may be, there’s undoubtedly something you can offer to help others on their journeys. Identify what that something is, and share it freely.

Luckily, many of the things that make someone an expert networker also apply to being a good human: Be true to yourself and your values. Be kind and thoughtful about others’ time. Be empathetic and a good listener.

And if any parts of the process don’t come naturally to you (like asking for help, talking about yourself, or connecting with strangers), remember that it does get easier with a little grit and a lot of practice.