Lessons from First-Time CEOs
Rob Reinfeld and I sit down to share what surprised us, and what keeps us up at night
Welcome back to The Workaround. I’m Bob 👋
You’re in good company with thousands of fellow entrepreneurs and innovators who read (or listen—see play button above) to my stories from a career in tech startups and corporate innovation.
I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.
I’m excited to share the next podcast episode in my series of conversations with interesting people on topics where business and life intersect.
My discussion partner this week, Rob Reinfeld, is the Co-founder and CEO of A2 Influence, a content development agency that helps leading brands and retailers create and distribute authentic content at scale. I told the story of our launch of A2 last April. Since then, the company has scaled quickly to become a leading player in the industry.
[Side note: Rob and I will be at Shoptalk in Las Vegas in March. Let’s meet IRL if you’re there!]
Rob was in town for a year-end celebration with his team a few weeks ago. With time to kill sitting in my home office, I began asking Rob about his first year at the company and his first CEO experience. Before he got too far, I set up some mics and jotted down notes from my first year in the same chair. The result was a fun conversation between two friends on a topic usually limited to EO meetings and coaching sessions.
Here’s a summary, a teaser, an amuse-bouche to get you to hit the play button above ^^^ or see our faces in two layers of company swag on our brand-new YouTube channel.
Plan for the Unexpected
The plan was pretty simple on paper: Relaunch our influencer marketing company with a solution very similar to what was wildly successful before. But Rob says, “We now have a completely different game plan today than we started with a year ago.”
The CEO of an early-stage company must have a plan—but expect to rip it apart once the market feedback rolls in. Rob describes pivoting with emerging needs in Retail Media Networks and with creative assets that can be used far beyond social campaigns.
But it’s important—and calming—to notice the things that don’t change over time. The advertising industry people and players, ways of working with partners, and many ingrained habits still work pretty much like they did when we started our careers decades ago.
You’re Always on Stage
At a recent get-together with former employees, a friend recalled several points that I shared during her new hire onboarding with me six years ago. Since I was the company CEO, my words made quite an impression. But I can’t remember what I said yesterday, much less that far back!
There are a few relationship dynamics at play. First, the CEO has the ultimate control over the company and each employee’s position. Second, employees have only one CEO, while the CEO has many employees. As a result, all eyes are on you.
The key to success is knowing this dynamic exists and using that power and influence for good. For example, I came up with the idea of personally onboarding each new hire and stuck with it as we grew. It paid off in building trust back then, and that trust continues to pay mutual dividends today.
Something Will Always Keep You Up at Night
Rob describes having trouble falling asleep in the company's early months. He was concerned about closing his first contracts and felt the pressure of responsibility to cover employees’ salaries and health insurance as growth came in fits and starts.
Today, his business is growing quickly and profitable, but he still lies awake thinking about work. Instead of survival, his mind now goes to the giant strategy game of choosing direction, building large partnerships, and investing for growth. “It’s like a real-life game of Chutes & Ladders.”
As his chairman, investor, and friend, I worry when Rob says he’s losing sleep at night thinking about work. But I’ve come to realize that’s the way he is—and it’s mostly a sign that he truly cares about his company and team. He’s got the wiring of a leader.
“Eat the Pizza”
We discussed our early work experiences, which influenced the types of leaders we eventually became as CEOs. Rob shared his foundational story of working at HBO and flying to a meeting with door-to-door cable salespeople in New Jersey.
He bought pizza for the group of gritty, hard-working sellers and prepared to give a motivational speech about the upcoming HBO lineup. But an old-timer pulled him aside and said, “Eat the pizza first.” In other words, show us that you’re one of us.
We agreed that Leadership 101 includes leading from the front: Never ask an employee to do what you wouldn’t do. Establish trust and teach by example as a peer of your teammates. Sometimes, you even rent the U-Haul truck and move tables yourself to save money for the company’s first Holiday Party. Thanks to that effort, Rob’s team and investors see how much he’s dedicated to their success.
When I pitched Rob on the idea of becoming CEO, I did not doubt that he would succeed. Seeing him take the leap and fulfill the promise has been a highlight of my career. I’m excited to see him inspire another generation of leaders as he and his team continue to grow.
To enjoy the whole chat, hit the play button above, subscribe to the podcast on Apple or Spotify, or watch us below on YouTube!
Helpful links:
How we might work together…
Fleet is our holding company for services businesses. We invest in leaders who are ready to start their own companies (we also do some M&A). If this might be you, Hit my Office Hours link.
Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions. CEO Jess Shuman is standing by to share a no-cost assessment of your business.
Shipwright Studio is our software development agency led by Ross Lewellyn, a CTO who has led multiple successful startups. He loves helping turn your dreams into reality, and our clients trust us for software built to last.
Hearty is our boutique recruiting service. Our difference is that you get C-level partners—including me!—to source and screen, resulting in killer talent in less time. When you’re ready, let’s chat.
Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Why Great Leadership Doesn’t Scale
It isn’t easy to find writing that explores why some strong work cultures last, and others don’t. Finding new insights into leaders’ behavior and how it impacts company growth is even harder. In his recent post “Why Great Leadership Doesn’t Scale (But Bad Leadership Does),” Jose Corella offers both.
His key point—backed by research and personal experience—is that charismatic leadership fails at a certain size breaking point, and you must instill the leader’s positive personality elements into Values.
This post is so smart and original that I was compelled to reach out and hop on Zoom with Jose. I learned he’s a long-time business operator with several years of experience as Chief of Staff. His spot in the organizational chart, his curious mind, and his confidence to share work to our advantage in this piece and many others.
If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏
Love the "eat the pizza first" story. Beautiful.