My 10 Biggest Mistakes in 10 Years as an Entrepreneur

I guess I’m now a 4%-er. According to Inc. Magazine just 4% of new companies make it to 10 years. And guess what? We just made it here at Convince & Convert. Our 10 year anniversary was yesterday! This is the longest I’ve ever done ANYTHING continuously (other than being a husband and a father), and I’m so proud of my team and the work they’ve done — and continue to do.

We’re so fired up; we even created a temporary new logo to commemorate the 10th anniversary of Convince & Convert.

I was an entrepreneur before I started this firm. In fact, Convince & Convert is my fifth startup endeavor, and I’m an investor in dozens of others. But this is certainly my most well-known and longest-running venture, so on this anniversary date, I decided to take some stock and think about the mistakes I’ve made along the way. I hope these confessions will help you in your own entrepreneurial journey.

There’s been a lot of successes, and I am incredibly thankful to my team, my family, and our remarkable clients, partners, collaborators, and friends for each of them. But me writing about what I may have done right isn’t particularly interesting, or illustrative, in my estimation.

Instead, here are the 10 biggest mistakes I’ve made in 10 years with Convince & Convert.

I Didn’t Delegate Early Enough

It feels like this is a classic entrepreneurial blunder. You trust yourself to do everything exactly how you want it done, and taking on more yourself is usually a pretty cost effective angle of attack as well. For the first four years of this company, I wrote every check, and spent every Saturday at my local bank branch depositing checks. Accounting is not something at which I am particularly adept.

Fortunately, I eventually realized that for a company to grow, the leadership of the firm needs to concentrate as much as possible on doing what they are UNIQUELY QUALIFIED TO DO. Now, I seek every year to delegate about 15% of my time to others at Convince & Convert. When you do that consistently, it concentrates your own time like a reduction sauce. Eventually, you start to use your own time more and more efficiently and effectively.

I’m not all the way there yet, and I still do some stuff I probably shouldn’t, but I keep working on it. Delegation isn’t a dereliction of duty; it’s how good companies get better. Further, it’s a symptom of great trust in your team, when you let go of things that your formerly held in a death grip of micromanagement.

I Was Late Adopting Systems

Are you a golf fan? If so, you’ll know exactly what I mean when I remind you that there are two types of golfers. The first are practice-based golfers. They have a lot of coaches, and spend a lot of time practicing. They are trying to groove their swing to make it flawlessly repeatable. The second type of golfer are feel players. They seek less coaching and practice less often, trusting their instincts and creativity to take over when they need it.

I am a feel golfer, but in business.

Thus, I’m guilty of believing that if I can’t remember something, it’s probably not worth remembering. I also abhor unnecessary meetings, structure, and process, as I believe it thwarts creative problem solving and breeds inefficient use of time.

This “go with the flow” attitude serves me well in the very early days, when indeed I could actually remember all that mattered. But I waited too long to flip the switch to project management systems, time tracking systems, accounting and finance systems. Fortunately, Kelly Santina, who heads our operations, came aboard and made me see the light about this and a great many other things.

Today, we are religious users of Teamwork Projects for project management, Sococo for communication, QuickBooks for accounting, and a flotilla of other systems to manage other elements of the business, including CoSchedule to maintain our editorial calendar.

I should have systematized earlier.

I Resisted Specialization For Too Long

One of the truisms of most small companies is “everyone wears a lot of hats.” This is equal parts a financial necessity and a cultural necessity. At first, you don’t have the cash to pay someone to do just one job, and it’s also good for esprit de corps when everyone is pitching in to do everything that needs doing.

But you can’t play that game too long, and I did.

It’s true in a lot of areas, but most so in our business development function. For a long time, Kim Corak handled biz dev for all three divisions: speaking, consulting, and media/content. She did an amazing job. But eventually, I realized that to keep moving forward, we needed more specialized skills. Now, Kelly and I handle most media/content sales, Kim focuses almost exclusively on consulting, and the sublime Michelle Joyce handles the speaking side.

This division of labor isn’t always perfect, but it’s much more sensible than putting everything on one person, and it’s enabled us to continue to grow. I should have done this earlier, too.

I Didn’t Set Appropriate Customer Expectations

As we grew, one of our challenges was making sure customers knew/know that while I see have input on everything we create and publish, I am not personally making every slide of every strategic plan, and I’m not writing every blog post on this site (although I did for a long time).

It’s hard to set customer expectations appropriately, especially when I am the most visible member of the team and clients think I will personally manage every project.

We’re very good at this now, and I’m careful to always talk about WE and rarely about ME when discussing the company and our capabilities. But it was definitely a tough transition for a while there.

Today, we have a similar issue, but with timing. We’re often at capacity on strategy projects, and on content projects, meaning that new opportunities may have to wait 3–4 weeks before we can commence work. Being better at setting those expectations accordingly is something I’m still working through.

I Gathered Too Little Customer Feedback

Related to the prior point, when I was fully in the middle of every project, and essentially quarterbacked everything, it was easy to not worry about formalized customer feedback. I had a handle on what customers thought of us, because I was personally talking to all of them, all the time.

Now that we have grown, and the team does more customer interaction than do I, it’s critical that we have a consistent, standardized feedback system so that we all know how we’re doing, and where we stand.

About 18 months ago we moved to a Net Promoter Score survey protocol, whereby we survey consulting clients at least twice during each project. We also use NPS for speaking opportunities, and we’re going to roll it out for media/content. I am incredibly proud that our NPS is 73 right now, which is very, very high and puts us up there with the best brands in the world.

I wish I would have started this program years ago!

I Gave Disorganized Feedback to My Team

Like a lot of entrepreneurs, I can be a bit of a handful. When I have “suggestions” I tend to offer them at less than ideal times, with less than realistic expectations for execution. I used to email Kelly all the time with “ideas” on things we could/should improve. I’m SURE she loved that!

And then I realized that every time I emailed her, she had to stop what she was doing and address whatever crazy idea I’d come up with in the prior 11 seconds.

Now — and this is especially key because we are 100% virtual and always have been, and we have very few meeting and calls — I send ONE email per week to our head of operations called SOMM: “stuff on my mind”. It’s a compendium of everything that I’m thinking about or upon which I request a status update. Putting all of this in one, weekly email and resisting the temptation to fire off random “but what about…?” emails, has improved operating efficiency dramatically.

I Didn’t Force Proximity EVERY Time

As mentioned, we are an all-virtual firm, with team members all over the USA, and beyond. On occasion groups of us will connect face to face at a client meeting or conference. But the full Convince & Convert team meets in person just ONE time per year, at our annual strategic planning retreat.

Of our nine retreats, the first one was in Phoenix (when I still lived there) because there were very few of us, and we had no money. Then, we started going to Puerto Vallarta, Mexico where we rent a giant house and the whole team (and their spouse/other/friend) lives together with harmony, good times, and good ideas.

We did Puerto Vallarta together in a house every year except for 2017 when we went to Santa Fe and stayed in a boutique hotel. And it was……..fine. But it was definitely not the same. In a virtual firm, in the rare cases when you do get together you have to make it count, and create as many opportunities for unstructured bonding and closeness as possible.

That one year, I didn’t. We did a hotel instead of a house. And it’s not like it killed the company or anything, but it hurt our cohesion a little, which is why we went back to a house this year.

I Pursued Ideas Without Execution

I’m an idea guy. Always have been. It’s why I love consulting. The challenge of figuring out how to improve someone else’s business is fun and exciting for me. But I’m guilty in my own businesses of letting the idea supersede the execution plan, and sometimes I pursue an opportunity without thinking it through 100%.

And it’s a fine line between a culture of trial and testing, and culture of going off half-cocked without a plan. I try really hard to land on the former, but sometimes I peek over toward the latter.

Perhaps the most egregious example is the ill-fated MarketingPodcasts.com project. This was — and maybe still is — a good idea, in my estimation. The premise back in 2013 was that podcast discovery is hard, and it was nearly impossible to find great marketing podcasts with any degree of efficiency. So, I decided to solve that problem. We worked with a dev team to build MarketingPodcasts.com, a sophisticated, algorithm-powered directory of marketing podcasts; like Google for audio programming. It worked, and people liked it.

Here’s the problem. I was so in love with the idea, and so convinced it solved a real problem, I never fully articulated how we were going to make money, or how MarketingPodcasts.com fit into our other divisions and programs at Convince & Convert. After a year or so (maybe less, I’ve blocked out the details!) we shut it down.

Lesson learned (I hope).

I Gave Up First Mover Advantage

A few years ago, I launched one of the first daily video programs in the marketing space, called Jay Today. It was before the Gary Vee show, and long before a lot of other programs of similar type and intent, of which there are now hundreds.

Partially because I was first (or nearly so), and partially because the content was at least decent, Jay Today got pretty good traction. Not Gary Vaynerchuk traction, but good by my mortal standards.

I did the Jay Today show three times each week for about 14 months. And then, I quit. I simply got tired of doing it, which is rare for me (my Social Pros podcast is 8+ years old). I think I just felt like I didn’t have anything else to say in that format at the time, and I sunsetted the show.

Afterwards came the big explosion in daily video programs and video podcasts. About 18 months after the end of Jay Today version 1.0, I returned with Jay Today version 2.0. And it was fine, but I’d lost my first mover advantage.

I let fatigue convince me to give away an edge I’d developed. That was a mistake.

I Picked the Wrong Competitors

In the early years, Convince & Convert was really just Jay’s blog, and operated as such. Then, as we grew it became a multi-author home of intermediate to advanced social media and content marketing advice and counsel.

Over time, we saw ourselves competing against Content Marketing Institute, Social Media Examiner, MarketingProfs, TopRank and other terrific online resources that publish daily articles with excellent, tactical, how-to guides to all things digital marketing.

We tried to fight that fire with our own fire, and our editorial approach here began to embrace volume and practical advice as key components.

I realize now that was a mistake. We’re not going to out how-to those great sites, and we never should have tried. We’re a thoughtful, strategic, consulting firm that works with many of the world’s most interesting brands to solve large and thorny marketing and customer experience challenges. We’re not in the how-to business, we’re in the “now what” business.

For a while there, our audience for our content was one persona, and our audience for our consulting services was a different persona. We’ve fixed that now, which is why we publish less frequently here than we used to, our content is purposefully longer-form and more detailed, and a lot of our stuff now is based on first or second party research.

We regained the right focus and are trying to serve the same, smart audience with both content and consulting.

I hope you agree. If you like what we’re doing here, you may want to visit this page to sign up for our feed, where we’ll send you a quick email each time we publish something new.

Thanks again for the opportunity to serve. Whether our relationship began today, 10 years ago, or anywhere in between, I very much appreciate your time and your trust.

And congratulations to all at Convince & Convert for being extraordinary every day, and for getting us to TEN YEARS! I don’t say it enough, but I love each and every one of you.