The Loneliness of Web Entrepreneurship

By on Freelance

In my early days — prior to selling my web agency and starting uGurus, a hub helping web professionals build successful businesses — I would read books that advocated “networking” as a means to build your business. Okay, great, so I attended a bunch of networking events.

More often than not, these events were pretty worthless.

One time I went to a Village Inn coffee shop, and as introductions went around the room, it occurred to me that a) I wasn’t in the market to buy a house b) I didn’t need a financial advisor because I was broke and c) I wasn’t going to take any vitamins that required me to sell them to my friends and family once I started taking them.

At one point in my “network everywhere” tenure, I joined a group called Social Selection that met at a bar once a week. The purpose of the group was to form business connections through a tight-knit group of social thinkers. I think it was on Tuesday nights. You see, I don’t really remember, because the real purpose of the group was to get totally drunk under the disguise of “networking.”

While I did form some lifelong contacts in this group, I realized that I needed something more meaningful to really impact my business.

Meaningful networking can be tough though. Especially in the web business. For most of our waking hours, our work ties us to the desk under the glow of the monitor. Getting out and shaking hands can sometimes be a huge leap.

Especially if you are an introvert. I’m not. But before I get into my tactics on how to conquer loneliness and build a stellar network, it’s important to know if you are an extrovert (party time!) or an introvert (hackathon!).

Are You an Introvert or an Extrovert?

I’m oversimplifying this to the max, but introverts build energy when they are by themselves and deplete energy when interacting with others. Extroverts are the opposite. They deplete energy while alone and build it while around others.

I don’t think personality definitions are totally black and white. There is a lot of grey. The important thing is to figure out which way you lean.

Are You an Introvert or an Extrovert?

If you find yourself totally beat after 45 minutes of networking, then you are likely an introvert. It’s going to be difficult to build a successful business if you just stay latched to your computer. Don’t avoid it, just make sure that you have plenty of alone time directly before and following an event. I would also be careful to not schedule multiple events per week. Probably just one event will do the trick. If you attend a multi-day conference, make sure you find time to fill up your tank by zoning out without people around you.

If you find yourself swinging from the chandelier after hour six at an event, then chances are you have extrovert blood. While this is going to make networking a natural talent of yours, it doesn’t mean that meaningful networking will be easy.

I fell into the early trap, as an extrovert, of just going to everything all of the time. I didn’t think much of my intentions. It was just like, “yeah, I’m going to that, and that, and that.” I failed to be strategic about the types of networking I was doing.

On the flip side, my business partner Steve Thiel, is an introvert. He approaches networking with a plan. He knows exactly who he wants to talk to at an event and the topics he’s interested in spending time talking about. He has the sense to accomplish what he wants to and get the hell out of there.

Both approaches can work great and we can each learn from the other. When I remember to “think like Steve,” I get the added benefit of being more strategic, but still leaving plenty of room for chance introductions.

Get Started With Your Industry

One of the best things I ever did was to start attending industry events. Whether it was local meetups about web design or big conferences like Adobe MAX, I forked up the money and allocated the time to get involved with people shaping the web landscape.

Getting involved in the industry of my craft helped me build a network of other experts around the world that I could rely on for contracting, referrals, and brainstorms.

Brent Weaver interviews attendee at Adobe MAX 2013
(Brent Weaver interviews attendee at Adobe MAX 2013)

Networking with other like-minded people is a lot easier than breaking into an industry where you have less in common. I like the idea of starting here because it feels natural. Getting to nerd out with fellow webophiles can help break the sense of work-from-home loneliness that we often feel.

You should look at what technologies you use and seek out local meetups around that. For instance, if you are building on WordPress, check Automatic’s website for listings of WordPress Meetups and WordCamps. Same goes for Drupal. has tons of other related meetups around design, development, and entrepreneurship.

My next move would be to attend events that you think possible channel partners might attend. I identified other marketing and ad agencies as great potential sources of continuous leads. There is a national organization called Ad Club that has local chapters all over the United States. This group was a treasure trove of great contacts that all needed web and digital subcontractors.

While it’s great to meet with other people that speak your own language, make sure you don’t overdo it within your industry. It’s easy to get lost in thinking you are making big progress with your craft, but failing to meet actual customers. Most of our customers aren’t going to be hanging out at events, unless of course you are just working with other web pros and agencies.

I highly recommend attending at least one national level event per year. You can expect to pay a decent clip for your conference pass as well as flight and accommodation, but it’s worth it. These events are going to be the cornerstone of you forming a national and international support network.

They will also give you a glimpse of the big trends. This is important when you are setting your annual strategy as a company. To know what big ideas are happening in web in terms of technology, design concepts, and business models.

I’ve never regretted spending money to attend a conference.

Focus on a Target Market

Keep in check how many of your own industry events you attend…unless of course web is your target market. Otherwise, make sure you allow time and money for attending events that your target market attends.

Brent Weaver and Steve Thiel attend industry conference on Connection & Collaboration
(Brent Weaver and Steve Thiel attend industry conference on Connection & Collaboration)

It’s possible to have many target markets, but if your marketing efforts are going to be effective, you need to pick a target for a fixed period of time.

Almost every target market has local, national, and international level events. Let’s take the example of restaurants. In Denver there is EatDenver, in Colorado the CRA, then there is a national conference and association. I’m sure you can find a TON of additional events surrounding restaurants if you open your target to food brands, supplies, and hospitality.

These are going to be structured very much like our own industry in that, on the local level, they are going to be driven by informal meetups, association-based events, and fundraisers. On the national and international level, they will be organized by the big associations and typically be conferences.

These events are going to be all about talking to potential customers. These folks probably don’t know much about what you do, so the objective in networking within these spaces is getting to know your customer.

You might find some customers, but I’ve found that conferences typically yield a high dose of customer research. More so than actual business.

Attending target market events always kept my technical brain in check. It also would give me a great sense for what the pains and challenges were in the market I was targeting. To go from a conference like Adobe MAX where I might be talking about the challenge of gracefully setting responsive design breakpoints to an educational conference where an attendee asks me, “why do I need a website?” can keep things in perspective.

The rest of the world isn’t thinking about the web as often as we might think they are. They are doing whatever it is they do and we are the ever-obsessed.

I would always err on the side of attending more customer-oriented events than any other type of event. Your business will thank you.

Do Some Good

Early on in my career, I started volunteering my time and expertise to help out causes that I was passionate about. A side effect of this activity was that I met a lot of really amazing people. These people, more often than not, had leadership positions within companies or organizations that they worked at or owned.

For years, this is some of the only networking I did. I didn’t attend industry events or events organized by my target niche. And I got tons of clients from doing it.

I didn’t just volunteer to move stuff. I had my company build websites for organizations, fundraising events, and auctions. I created branding packages, flyers, and business cards.

I went all in.

Brent Weaver presents donor plaque to library in rural Ethiopia
(Brent Weaver presents donor plaque to library in rural Ethiopia)

I went to Ethiopia on four different occasions. I helped raise hundreds and hundreds of thousands of dollars. Served on two different board of directors and eventually was President of a non-profit that built libraries in Ethiopia.

The point wasn’t to network. It was to help save the world and leave this place in better shape than I found it. But, I built an amazing network.

Good people do good.

If you have any feelings of loneliness or lack of network, then start volunteering. Ride the wave for as far as it takes you. Even if that’s a tiny village in rural Ethiopia.

Create a Mastermind Group

My last and final suggestion to help you overcome the loneliness of web entrepreneurship is to form a mastermind group.

Mastermind groups can come in a variety of different formats, but what is a mastermind?

Mastermind groups offer a combination of brainstorming, education, peer accountability and support in a group setting to sharpen your business and personal skills. A mastermind group helps you and your mastermind group members achieve success.” – The Success Alliance

I have participated in a few over the last several years, but the most effective has been a monthly group that I meet with under strict confidentiality. My group is made of only four people. I have seen successful groups of up to about twelve, but smaller is usually better.

I have also heard of one-off events that attract thirty to forty people for an all day session filled with bar camp presentations. This is a great format for sharing a lot of ideas in a short period of time, but this size of group would need to be broken into smaller sub-groups for higher touch, confidential sharing to happen (which I highly recommend).

At my regular group, we block three hours over an extended lunch for our meeting.

We never miss a meeting. No matter what. We even have a structure of fines for being late, answering your cell phone, or needing to reschedule a meeting. If you are late: $50. If you answer your phone: $50. Rescheduling a meeting: $100. So whatever it is that might make you inconvenience others in the group better be worth the fine.

Every month we get together and review a four quadrant square of our life: business best, business worst, personal best, and personal worst.

My group digs deep to find that top 3% and bottom 3% in our lives that we don’t want to tell anyone. We review our biggest hopes and fears and share stories and experiences as a method to learn from each other.

This absolute top and bottom needs to be covered by a group of peers that meets under a strict confidentiality agreement. You either need to join a group like EO to hop into an existing structure, or create one yourself. I was in EO’s incubator three years ago, and even though I am no longer in Accelerator, I continue to meet with my group every month.

Our group steers clear of advice and focuses on experience share through Gestalt-based leadership. Typically, each month one of us presents on a topic that is important to our life. These presentations usually get a few hours of prep time from the presenter and a coach prior to our monthly meeting.

Over several years of having a monthly mastermind group that is confidential and safe, I have found that I have a place to voice concerns that I would have otherwise kept bottled up. Things about my relationship, family, and business can get perspective from my group prior to bringing them into the light of the rest of my life.

Confidentiality is the strongest of contracts in this group, so I can’t really discuss specifics of what we’ve uncovered. But I know that my personal and business life would not be able to achieve what I can today without them.

I think having a regular, confidential mastermind group is a requirement for any entrepreneur.

Event-based networking and doing good will only take you so far. Masterminds get into the deep and meaningful topics. You might opt to participate in a business or idea-specific mastermind instead of a business and personal focused-group like mine. That is totally fine.

The basis of a mastermind group is that you share. Ideas do best when you shine the light of others onto them, and they usually get even better when the
two different ideas have sex (think “video + internet” or “encyclopedia + internet”). Masterminds are a great place for this.

Overcoming Loneliness is a Marathon

When I first moved to Denver, I didn’t know anyone. Seven years later, it’s hard not to run into people at the art museum, book store, or grocery store. One time I was out in LA at Hotel Standard on the roof playing ping pong, and I ran into one of my Denver contacts. Now this doesn’t really mean anything except that I feel anything but alone.

My network is the first place I go when I need something. If I’m making an important hire, thinking about a new idea, or wanting to meet new customers, my first question to myself is, “who do I know?”

From there I find the best people, answers, and customers.

If you are feeling alone in your pursuit of success…or if your only human interaction happens in less than 140 characters, then it might be time to think about your network. But take my advice, don’t go to a “networking meetup” at Village Inn.

Be intentional about how you get out of the basement. Make it meaningful by attending industry events, meeting customers in your target market, volunteering for a great cause, or creating a mastermind.