Backing the Next Captains of Industry
Our story of founding A2 Influence and building Fleet, our service-focused holding company
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
This is an exciting post because I get to finally tell the stories of two new businesses my team and I have launched!
You see opportunity in many places and people when you’ve been an entrepreneur long enough. After riding the highs and lows for a couple of decades, the fear of failure becomes insignificant. And when those negative voices fade, we see nothing but possibilities waiting for a little fuel to fire them.
That was the story behind our last company launch, Shipwright, a software development studio I wrote about here in December. We backed our business partners, Ross and Chris. Just four months later, they are off to the races with several projects under their belt and weekly conversations with new prospects who need help bringing their ideas to life.
Their success got us thinking about other ways we might scale our experience in and love for services business. But it took another big leap that fell into our laps to find our calling.
Startups Deserve a Sequel
Successful superhero movies always have sequels, so why can’t super-successful companies do the same?
Well, it actually happens more often than you might know. It’s not unusual for company founders to build a business, sell it, and then start a similar business all over again…and again. Sometimes an entrepreneur buys back a business after the company they sold it to screws things up.
We’re now joining that club. It started with a handful of texts and a party…
It’s a late afternoon in March 2023. I’m at my home office desk plowing through emails before calling it a day. I’ve had my phone in do-no-disturb mode so that I can focus, but it’s time to see what’s been happening in the real world. I’m pleasantly surprised to see messages from friends I worked with at Ahalogy, the social+influencer marketing company we sold in 2020.
It seems that everyone but me is in Las Vegas for the annual ShopTalk event. It’s one of two big conferences in Sin City for the CPG and Retail Media and Marketing industry. It’s a chance for companies to show their latest and greatest innovations, and there are speakers on key topics. But it’s mainly a reunion of everyone in the industry and a chance for people to renew their relationships. After two years of sitting at home through COVID, folks are ready to bond again. The texts I receive are something like this:
“Lots of people are coming up to me saying they wish Ahalogy were still around.”
"My new company tried to build an influencer product, and it failed—we need Ahalogy back!”
“I thought you’d appreciate hearing how much people still remember and love what we built.”
They are right. I love hearing this. Companies always come and go, especially in the Age of Disruption. Three years after selling and leaving the company we built, I had not paid much attention to the industry. I am surprised other companies haven’t realized how to duplicate our success by now.
I quickly text my friends to thank them for their kind words, and then it’s time to go. I’ve got plans to attend an anniversary party for a company my friend Michael Stich has invited me to down the street.
Michael’s digital agency started just a few years ago in an interesting way: A small group of agency entrepreneurs met after selling their firms to the same holding company. They guided their businesses through multi-year earnouts and stayed on to take senior roles. But they got tired of being in big bureaucracies and missed building. So they quit their jobs, sat through their non-compete periods, and teamed up to build a new agency. They named it CourtAvenue and called up their old clients, who were eager to work with them again.
As I walked through the streets of Cincinnati, my mind put two and two together…Why don’t we do the same thing?!
Daring to Dream—Again
I had actually tried to buy Ahalogy back a year earlier after hearing that the parent company was considering “strategic alternatives.” I spoke with the CEO, who showed some interest but then ghosted me. I guess he had other priorities on his mind.
When I get to the party, I have questions for the CourtAvenue team about their founding story. How did they set things up? Did they build differently the second time? Then, I run back home to call my business partner, Ryan, and pitch him the idea of re-starting our influencer business. He loves it, and we start planning.
Our biggest step over the summer is chatting with former clients and industry experts to make sure there’s still strong demand for our service model. We learn that many others miss us, and the industry need has grown significantly.
Ryan and I assembled financial models, funding plans, and potential teammates. We’re mostly following our previous playbook, which worked incredibly well. This includes insight-driven content, trusted micro-influencers, and an obsession with Full F*cking Service™.
But at least one thing has to change from our previous company: I’m not going to be the CEO, and Ryan won’t be the COO.
We put together a team that has been running well independently without us for years. They’ve got the knowledge, the relationships, and the energy to return to glory. This time, our role is to provide some funding and guidance and GTFO of the way. It’s a cast of brilliant characters who are having an amazing time working together.
We’ve got to come up with a new name. We land on A2 Influence, which hits on a couple of positioning keys: (1) It’s our sequel, the next evolution of social, influencer, and content marketing; (2) We pride ourselves on building a service model that covers every element from A to Z; and (3) A2 is slang for “amazing” according to the young folks and Urban Dictionary.
Two weeks ago—a year since those fateful texts—I’m at ShopTalk with some members of our A2 team. Since our fall launch, we’ve signed several big contracts and many more are in the works. The team is full of smiles as we catch up with old industry friends and press the flesh with new ones.
And I notice that I feel different this time. I’m not the CEO. I’m the investor, supporter, and “Chairman.” Mentally, I feel that I work for this team rather than the other way around. I have that same feeling working with Ross and Chris at Shipwright. And as we’ve gotten into this Service+Backing model, it got us thinking about doing something bigger…
Scaling Service Business Success
There are two theses that we deeply believe. The first is that service never goes out of style.
In a world where SaaS soaks up all the VC money and media headlines, people forget that well-run service businesses are wonderful. Customers have jobs to be done, and they continue to pay gladly to have them taken off their hands. While software can help with workflow efficiency, most people don’t have extra time to put their hands on keyboards to do that work themselves. That’s why most B2B software companies have big service teams. And that’s why there will always be law firms, recruiters, accountants, hairdressers, dog walkers, software studios, and marketing agencies.
What’s more, there’s always room for new entrants. These businesses do not require boatloads of VC money to get off the ground. Because service is about human-to-human work, there’s less chance for some new tech to enter, disrupt, and grab monopoly power. In fact, if you keep doing your job well, your customers will stick with you forever.
We’re excited because we’ve been scaling up service businesses for the past twenty years. I’ve shared a fraction of those lessons of failure and success in this substack—and there’s a LOT more where this came from. Now, we can share these tips and tricks directly with more business leaders.
Our second thesis is that there are many amazing service business leaders who can and should lead their own businesses—as long as we can de-risk some elements of the leap.
Here’s the thing: Entrepreneurs are rare and a little crazy. Very few people are willing and able to risk their life savings, go without a salary for many months, and figure out all the stuff it takes to start a business on their own.
On the other hand, many stellar leaders have the skills and mentality to “own” the business they work on. But today, they don’t have a real ownership stake in the business they are building. Often, they work in a company that fails to appreciate their talents and puts barriers in their way.
These two core beliefs convinced us to formalize what we’re doing by launching Fleet…
For enlightened leaders who want to reach the heights of their potential, Fleet is a service-focused holding company that provides investment, support, and guidance to build high-performance organizations.
The Fleet brand name came from our continued love of the sailing analogy, which I wrote about here on high-performance organizations (HPOs) a few weeks ago. We’re a “fleet” of ships now. And we’ve got a website and logo to make it all official:
There are three benefits we’re bringing to the table for service leaders that we back:
Financing—We want to de-risk and de-fear what keeps many leaders from taking the plunge. Money is often the issue. So we offer capital to cover salary and benefits, a line of credit to cover working capital (so you don’t have to pledge your mortgage to a bank), and other compliance costs like corporate insurance.
Operations—Our team takes care of the important back-office stuff that often gets in the way of sales and service. We handle set-up activities like incorporation, payroll, contract creation, and employment agreements. Plus, we can offer shared services like HR, recruiting, accounting, legal, creative, and software development—in part by tapping into fellow Fleet companies.
Leadership Development—Running your own business can be lonely, and while leadership groups such as EO or YPO can be helpful, they are peers, not business partners. And we don’t think you should have to sell your company to private equity to get help reaching the next level. Plus, we’re operational partners, not detached finance people. We bring our toolkit of useful processes for areas such as strategic planning, problem-solving, team building, and accountability.
I’ve spent the last three months talking to current and potential leaders in various service sectors. Their feedback has been great. And I’ve also learned a lot from them and their success. This has helped us develop a list of what we’re looking for in “Captains” to back:
Strong service experience and a unique perspective on the business.
Ability to deliver clients—which is always critical to a fast start.
People skills and a history of developing employees.
Industry-wise, we’re going to be pretty agnostic. There are countless ways to win and many general commonalities among varied service businesses. We’re also looking to back new businesses and invest in helping current businesses reach the next level.
As I head into this “final chapter” of my work career, I am incredibly motivated to back enlightened leaders so they can scale high-performance organizations. Our vision is to create a multi-company platform where dozens (then hundreds, then thousands) of people come together to provide world-class services to clients in need—resulting in decades-long relationships for all of us. In other words, let’s do work we love with people we love working with for as long as possible.
So, if you’re ready to Captain your own ship or want to take your business to the next level, click the Office Hours link below and let’s talk.
And if you want to be a part of the ride on one of our companies, watch this space. We’ll be posting jobs here soon!
How we might work together…
Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
Looking for Influencer Marketing and Content Creation? The team from our previous company is back by popular demand with A2 Influence. We’re ramping up now and would love to share more.
Feel free to schedule time together during my Open Hours for questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
This Substack is now in Podcast form!
At this point in my life, I probably consume half of my content in podcast form. Podcasts are a great way to learn something new while walking the dog, driving, or working out. So, I’ve been tempted to try the new Substack podcast feature if you, dear subscriber, prefer an audio version.
I was convinced to finally jump into the pod pool after listening to my friend Brad narrate his latest post. This gave me something interesting to listen to during my workout, and I loved hearing Brad’s voice—a bit of asynchronous communication joy.
Whelp, I’m a podcaster now—like half the human population? You can hear the first episode here, a recording of last week’s post. You can find links to subscribe here. I’ve even included a few added story details exclusive to the recording. Please listen and let me know if you prefer this format—that’s the only way I’ll know if it’s worth continuing!
Well done! I took a deep breath and launched my latest effort in Manila last week, my third small, service-based business. Exciting as it is, having done it before, I feel like I am back at the bottom of the mountain looking up a summit obscured by clouds and wondering if my now 45 year old mind and body will carry me up there again. I have adopted healthy new habits and dropped old ones, and I am much more discerning about how I spend my time and who with now. But make no mistake, it's always an effort. One thing I can say for sure though, it's also always worth it in the end and I have never, ever, not once, EVER regretted working for myself. Fingers crossed for you my man!