From a lobster boat in the small fishing village of Spruce Head, Maine, to Silicon Valley and back again, I’ve just about seen it all! I’ve learned a lot along the way and want to share these six important lessons for aspiring entrepreneurs.
1. Pack your backpack
While many of us are inspired to become entrepreneurs and leaders, most of us are not ready to answer the call when it first comes. I was successful early in my career working at newspapers in Maine before, during and after college. But I also had this drive to build something and realized there were key skills, experiences and connections I needed to make it happen.
I call it “packing your backpack,” and over the years, I’ve mentored other entrepreneurs and executives to help pack theirs. It’s about specifically seeking out professional experiences, knowledge and connections with people to develop the skills you need. For me, this was a BIG part of my success. It’s also an ongoing process.
2. Big things can come from small places
It started in 1995 working with internet pioneers in Portland, Maine at the Portland Press Herald. I was selling online services to local businesses, and a lot of car dealers. I’ve always loved cars (to this day I can still name ones from the 60s and 70s just by looking at the grills!), so working with car dealers came naturally to me. I had an idea to revolutionize how people bought cars by moving the process online. It was an obsession; I even bought large Post-it notes, drew out the plan and stuck notes on every wall of my apartment. This would later be known as cars.com.
After looking to see if anyone else had thought of something similar — keep in mind, this pre-dated the internet — I couldn’t find anything except for an email listserve discussing the general idea. I joined the conversation and was later called by an executive at the Chicago Tribune saying they wanted to fly me to Chicago to discuss the sales opportunity. The Post-it notes came with me, folded up in my bag. When they asked me to describe the idea more fully, I brought them out. They said “Check, please” and I was off to Chicago!
3. You don’t know what you don’t know
This can sometimes be good, but in this instance, it means I didn’t know I wouldn’t financially benefit from this idea. Investors made hundreds of millions of dollars off Cars.com; one of the investors I brought on put in the term sheet that when it was profitable, I would move to their company and build a national network and platform for them. I laughed with the Cars.com CEO, thinking it was going to take a while due to the amount of cash they just took in.
But Cars.com was live in 87 markets in just 154 days, and after about 11 months they were not only profitable, but rolling in it. It was an incredible ride. When the same investors called the note and asked me to come to Silicon Valley, I didn’t realize the immense amount of Cars.com stock wouldn’t come with me. You don’t know what you don’t know.
4. Disruptors may look naive, until they don’t
In Silicon Valley, my job was to build the national network of 67 newspaper websites, drive all of the online revenue (top source was Cars.com), and work on investments. I received early pitches from Netscape, AOL Digital Cities (both of which I invested in and benefited the company), and the predecessor of LinkedIn (which I helped pivot to the site it is today).
Between my time in Silicon Valley and starting Dream Local Digital, I worked in online marketing and noticed how it radically changed how people got news and information. When I spread the word to media companies and suggested they shift, they laughed at me. While people liked having me at their conferences because I taught them what Twitter was, they missed the key part of the message: social media was going to change the world.
Dream Local Digital was founded in late 2008 after I finished a conference and realized they weren’t going to do anything. But I would.
Once I got started, Facebook was pre-revenue and I had just started working to launch Google Ad Words — which brought in millions of dollars a week. The idea was that small businesses needed online marketing advice and support from someone they could trust; Dream Local Digital was built to support media companies by offering those services to their advertisers.
Now, 86% of every dollar spent in online advertising goes to Facebook and Google, and newspapers across the world have been shut down or taken over by private-equity firms. Disrupters may look naive, until they don’t.
5. Don’t be the frog
I built Dream Local Digital with a dual mission: to help media companies transform by generating digital revenue and client relationships, and to help small businesses succeed.
To date, Dream Local Digital has helped more than 65,000 small businesses throughout North America; and at its height in 2019, was answering the phones under 75 different brands nationwide. Direct business was less than 20%.
Year after year, media partners were only selling a tiny fraction of what they should be, but I kept working harder: educating them, training, and flying all over North America to meet with small businesses to show them how it’s done — I just didn’t realize I was a frog in a boiling pot of water. Despite the fact I had seen so many other trends early and clearly, I didn’t want to believe this one. When COVID hit, Dream Local Digital lost 56% of the business in six days, largely because the media companies had such weak relationships with their clients that it was the first cancellation call.
We’ve pivoted and built up direct business, which is now more than 50% and growing. This lesson made me take a hard look at other aspects of the businesses, trying several different niches until we hit our sweet spot. Now, Dream Local Digital is working with growth and scale companies in several industries in Maine and nationwide to market themselves online. It’s going to take us another year or potentially two to recover, depending on the economy (which is tough in the marketing industry right now). But clients are seeing huge impacts, which is immensely gratifying.
6. Most important trait needed: perseverance
The journey of entrepreneurship is more like a roller coaster than day-to-day life, and scaling is never a straight line. The most important trait any of us needs is perseverance. It may take time, but you can make it happen!
Do you need help growing your company? Dream Local Digital can help! Visit our website to learn about your package options.
