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It’s easy to think that successful individuals fall into their own elusive class of people. We assume they have something the rest of us don’t — some “it” factor that makes them magically successful while the rest of us are just average.
But when you look at their stories — the actual roadmap for their success — you realize they aren’t unusual. In fact, they’re quite average. They just took a very specific series of actions that set them up for success — actions that are replicable.

In this post I’m going to break down the career journeys of three well-respected and successful professionals: a top-ranked podcaster, the VP of Marketing at a groundbreaking startup, and the CEO of a marketing agency for real estate agents. We’re going to look at where their careers started, and the specific steps they took to go from “average” to “extraordinary.”
And we’re going to answer that burning question I hope you’re now asking: if they don’t have a magic “it” factor, then what did they do that made them so successful, anyway?
Let’s find out.

Christopher Lochhead: 3-Time Silicon Valley CMO, Best-Selling Author, and Top 5 Business Podcaster

Christopher Lochhead, when you look at him, seems like one of those exceptional people who’s got everything figured out. He’s been the CMO (Chief Marketing Officer) of three different Silicon Valley companies; he’s the author of two bestselling business books; he brushes shoulders with the Silicon Valley greats, and he hosts a podcast where he interviews the likes of Kerri Walsh Jennings (the Olympic volleyball superstar) and U.S. Four-Star General Stan McChrystal.
Sounds pretty unattainable, doesn’t it?
But when Chris was 18 years old and failed out of school (he was later diagnosed with both dyslexia and dyscalculia), he didn’t seem like he was on a trajectory to go much of anywhere. He was just another late teen/early twenty-something trying to figure it out.
That’s much more relatable.
So how did Chris go from an 18-year-old expelled student to a 27-year-old working at the head of marketing at a publicly-traded Silicon Valley company?
You’ll notice a trend pretty quickly in these stories — they aren’t linear. At 18, Chris’s passion was music, and he worked as an orderly to pay the bills. He didn’t feel like he was on a trajectory to go much of anywhere, so when his friend suggested they start a business doing technology training and custom programming (way back before the dotcom boom), he said yes. His friend had a technical background, so Chris took on the non-technical parts of the new business — sales and marketing.
The business grew for three years, but expenses grew faster, and he and his business partner went into debt and had to shut the operation down.
This is the first takeaway from Chris’s story: when you run into a challenge, you can take it in one of two ways: as the end of the road, or just a bump. You get to choose.
In this case, it would’ve been easy to say “My entrepreneurial venture failed. Clearly I’m not cut out to be an entrepreneur.”
But Chris took it as a singular failure, not an indication of his potential (or lack thereof). He tried again. An entrepreneur in his network invited him to join his boutique consulting company as their first sales hire, and Chris said yes.
While working in consulting, Chris started to observe a new trend in the business world — the adoption of customer servers and databases (later known as CRMs). Chris jumped on that wave too, and worked to become a knowledgeable commentator in the space — a thought leader, guru, and consultant. He spoke at conferences and slowly built a team, which morphed into a company, which became the venture he eventually sold — a sale that propelled him into the Silicon Valley startup space as a head of marketing at the age of 27.
This is the second takeaway from Chris’s story: learn to see trends and needs in the business world, and when you find them, ride the momentum of that wave. Sometimes it means starting a company, and other times it means joining a company already existing in that space. But getting smart and learning to see opportunities is key for putting yourself in the right place at the right time.
Once he was in Silicon Valley, he was able to grow in his original marketing role, then beyond it. In the years since moving to California, he’s been the CMO of three different publicly traded companies, then used his marketing knowledge and connections to start and build his podcast. He wrote two books on the idea of “category creation” — building companies that don’t just compete with existing ideas, but design and build something entirely new.
That’s a pretty good portfolio for someone who was kicked out of school, isn’t it?

What can we learn from Chris?

  • Your past failures, struggles, or average-ness doesn’t predict your future. Failure is the world saying “no, not right now,” not “no, never.”
  • Learn to identify opportunity, and be prepared to jump on it when it comes along, then ride the momentum that opportunity brings. Learning to identify opportunities comes from experience, and seeing what works and what doesn’t — but being prepared to jump on those opportunities comes from working hard while you’re waiting, and building as much skill and expertise as you can.

You can learn more about Chris’s story here, here, and here.
Fun fact: Chris also did a group call with Praxis participants last year. You can find the recording of the call published as an episode on his podcast!

Dave Gerhardt: VP of Marketing at Drift

Maybe you’ve heard of Drift — and if you haven’t, then I’m excited to be the introduction to a brand name I’m sure you’ll be hearing again. Remember how we just talked about category creation with Christopher Lochhead? Drift has built an entirely new category in the marketing space, and their growth isn’t slowing down.
Back in 2015, Dave Gerhardt was the company’s first marketing hire. In the four years since, his name has become synonymous with greatness in the marketing world. It might surprise you to hear that his first job out of college was at the same golf course where he’d worked in high school. Yes — really.
Gerhardt graduated in 2009, when the job market was slow, and he applied to hundreds of open positions — anything he could find — until he landed a 6-month internship. He took it, then turned it into a full-time position after the 6 months were up.
There are two keys here that are worth examining:

  1. Even though he had a college degree, he wasn’t too good for an unglamorous internship.

    It’s a common fallacy that taking a job that’s “beneath you” will limit your career prospects, but it didn’t hurt Dave. If anything, it was integral to his success, because it got his foot in the door, and once he started working he was able to level up. It doesn’t matter where you start — you just have to start somewhere.
  2. He took his opportunity and he grew beyond it. He went in and made himself so valuable that they wanted to keep him after his contract period was over.

    No matter what your opportunity, you always want to go above and beyond. The better you do, the more opportunity you gain, the more you’re qualified for, and the more valuable you become on the job market.

In the following years, Dave bounced between a couple different jobs, eventually relocating to Boston, where the best tech action of the area was happening. As he settled in Boston, he realized there was an opportunity — there weren’t any podcasts covering the tech scene in the city. Seeing an opportunity to build both a brand and a network, he started a podcast called Tech in Boston.
This is the next key to Dave’s success: he took on a side project that offered huge networking returns — as a side effect. He ingrained himself in the tech world of Boston, which led him to make valuable connections.
Perhaps the most fortuitous of those connections? David Cancel, the founder of Drift. He interviewed Cancel for his show, an episode that later became one of his most popular. A few days later, he reached out to Drift’s recruiter. He knew they were looking to start building their marketing team, and he pitched himself to be their marketing hire — and got the job.

What can we learn from Dave? 

  • The road to success isn’t straight, or even consistent, but the actions are: consistently pushing yourself to get better, seek opportunity, and build your professional value.
  • Side projects are extremely valuable, especially if they help you build both skills and a network. One of the things Dave’s best known for is the podcast he runs with David Cancel, which his previous podcast experience helped prepare him for.
  • Don’t be very picky about where you start. Just get started. The rest will sort itself out as you go.

Learn more about Dave’s career journey here and here.

Tim Chermak: Co-Founder and CEO of Platform Marketing

Tim Chermak is the co-founder and CEO of Platform Marketing, a national advertising agency that specializes in marketing for real estate agents. His company routinely doubles the annual income of its clients, and Tim treats his 20 employees well — offering 40 days of paid vacation per year. 
But when Tim dropped out of college, he didn’t have a vision for building a company like this. Real estate marketing wasn’t even on his radar. 
But Tim was curious, and so when he became interested in studying marketing, he followed his curiosity. When we’re curious about things, there’s usually a good reason, and it’s good to follow those curiosities and see where they lead us. In Tim’s case, it led him down a great career trajectory.
After he dropped out of school, Tim read extensively — and this is the first key takeaway. Tim didn’t go to school for marketing, but he’s studied it to a level where he can claim expertise. He’s made it his business to read about every part of the topic — history, psychology, different schools of marketing, the story of successful marketers.
His level of knowledge is undeniable. And being an expert in your field is really important if you’re pursuing success.
Once Tim had built up a level of marketing knowledge, and felt confident in his ability to try his hand running a marketing campaign, he started going to the local businesses in his hometown and pitching them on hiring him to do marketing. He went to 12, to be exact — because they kept turning him down.
This is the second key takeaway. Tim wasn’t measuring the validity of his idea by whether or not the first person he pitched said yes. The fact that he planned to become a marketing consultant was an absolute — the only question was who would say yes. He knew what he wanted to do, and he was committed to keep chasing that goal until somebody agreed to hire him.
And eventually, someone did. The small business he started marketing for performed well — very well. He gained a powerful portfolio piece — real proof of his marketing ability — and he started to get referrals. He picked up new clients. One of those clients was a real estate company, which he was able to work with to create significant growth. Seeing the potential in the real estate space, he started to niche down and focus his efforts. His freelancing portfolio grew, the level of work outpaced what one person could handle, and he started hiring his first employees.

What can we learn from Tim?

  • You don’t have to know exactly where you’re going, as long as you keep moving forward. You’ll find your niche over time — and when you do, you’ll be equipped to crush it through your past experiences.
  • The more you learn, the better equipped you’ll be to grow. Read whatever you can find about the topics that interest you, and pursue expertise.

You can learn more about Tim’s story here and here.

So what are the key takeaways from all of this?

You won’t follow exactly in any one person’s footsteps, because everyone’s path is different, and so are everyone’s strengths — and success comes from finding a niche you’re equipped to excel in.
That being said, there are some key things you can take away from this.
Successful people don’t have some special magic that makes them more successful than average people. They didn’t get a special break on their first try. They’re just willing to keep putting in the work until they get the results they want.
Even though they aren’t magic, they are smart about what works. Each person featured here became more specifically focused as opportunities arose over time — whether it was starting a local podcast as a networking tool, or becoming more specific with a business plan as a niche became apparent.
They’re unshakable — or as Nassim Taleb calls it, antifragile. They don’t get discouraged when the first thing doesn’t work. Success is inevitable — the only questions are how it will happen and how long it will take.