April 28

Words of Wisdom for Entrepreneurs

Today marks 13 years since I founded Converse Digital with no money, no clients, and a whopping 2-week notice. Over the last thirteen years, I've tried to stop each year, recap the most important lessons I learned, and share them with the world via this blog. I haven't made it every year, but I'm batting slightly more than 500, which would get me a big fat MLB contract, if we were talking about hitting baseballs instead of writing annual blog posts 🤣.   

If you're curious to read past missives, you can find them all here. I just reread them myself, and it's amazing how the same lessons resurface. I guess that either means I'm pretty hardheaded (keep your comments to yourselves 😊), or maybe I'm starting to understand the core wisdom of successful entrepreneurs. I'll let you decide as you read this year's six key lessons for successful entrepreneurs. 

Never Stop Learning 

Not only can old dogs learn new tricks, success today (and I'd argue every day in the future) requires a constant commitment to learning. Heck, when I started Converse Digital in 2010 as a social media agency, social media as a marketing channel was only about 2-3 years old. I, like everyone else, was self-taught and self-teaching as we went along. 

Fast forward to 2023, and I'm still largely self-taught and self-teaching. Case in point, Artificial Intelligence or AI as it's more commonly referred to in the news. I've spent countless hours playing with the technology, reading about the various platforms, and listening to people who know a lot more about it than I do explain what is possible today and in the near future. 

Why would I, an old dog myself, invest time in learning this new technology versus assigning it to someone on my staff? Primarily because I'm kind of a geek at heart. But just as importantly, while a staffer can brief me on the technology, they don't have my mind. Their mind may not connect the same dots as mine will. And if I'm going to make sales & marketing recommendations to a client — ones based on applying AI technology in their sales & marketing tech stacks — I have to KNOW what I'm talking about vs. parroting what someone else has shared with me

And trust me, clients absolutely know the difference. I've seen it firsthand over and over again in my career. 

Persistence Pays 

As I sit and pen this post, I'm actively negotiating the final aspects of a project contract that has been almost ONE YEAR in the making. No kidding. I just looked it up in my CRM. On May 10, 2022, a prospect responded to an email I sent as part of an outreach campaign. The initial proposal was sent to the prospect nine days later. And if I'm lucky, and the contracting folks are negotiable on a few essential items, I'll finally count this prospect as a client almost 12 months later.

Along the way, I've sent emails, texts, left voicemails, had additional conversations, sent 3-4 different versions of the proposal, each time addressing new hurdles, and had all but given up on this proposal ever becoming a new project. 

Then, BAM! Out of the blue, I receive an email that it's "go time," and they need the proposal revised one last time, and then they're going to sign it and get it into contracting. 

It's not the first time I've experienced this phenomenon. That doesn't make it any easier or less frustrating. And that frustration still produces lots of sales of 🥃 in my neighborhood 😂.  

But the truth is, very little comes easily in the entrepreneur's world. It's unfortunate. But real. Stay the course, and more often than not, you'll find success at the end of the effort.

Your Past Doesn't Have To Be Your Future

When I started Converse Digital, we were a social media agency. It made sense. I had become known for social media knowledge. I was giving social media & social selling keynotes all over the world. And our clients were all B2C social media management engagements. It was the obvious move and niche positioning. 

Then, in late 2012, Pearson Publishing approached me about writing a book about social selling. We weren't doing much social selling work for clients, but I was frequently delivering Painless Prospecting keynotes and workshops all over the US at conferences and agency network meetings. And that work caught the eye of the acquisition editors over at Pearson. And in short order, I was contracted to write The Invisible Sale

But I never really embraced the B2B social selling side of Converse Digital's positioning in the marketplace. I never felt we had enough social proof, or maybe it was just imposter syndrome. But, for the next eight years, Converse Digital primarily served and pitched B2C social media clients with a little B2B social selling side hustle. And that was fine because we had a good run and grew in revenue and profit. 

But increasingly, I was becoming bored. Social media was no longer innovative. Everyone just wanted to "go viral" or do cool stuff. The rise of Influencers was the last straw. 🤦‍♂️ It was time to shake things up. It was time to finally turn that social selling side hustle into a full-time job. 

So, in the summer of 2021, I started to pivot Converse fully into a social selling agency offering both sales and business development training and sales enablement tool development. There was only one big, actually HUGE (spoken in my best Trump voice), problem. We lacked any social proof of our efficacy in developing and deploying social selling programs. And trust me, as I've learned over the last few years, it's a big deal. 

Sales training prospects all want to see case studies of past successes. They want to see a list of client logos from companies that had hired us in the past. I get it. It's air cover. It gives plausible deniability if the engagement goes poorly. Let's face it, there is a reason "nobody ever got fired for hiring IBM" back in the '70s and '80s. And it wasn't because IBM had the best technology or solutions. 

It's kind of silly when you think about it. I even tried to point this out to a prospect on one call.

She asked about our case studies. I told her we didn't have any that I could share.

There was a pregnant pause. 

I asked if that was an issue. She said yes. How could she demonstrate to her bosses that she was making the right decision?

I asked her if her current sales training agency had case studies when she hired them. She said they did. 

Then I said, "But yet, here you are talking to me about replacing them as your sales training agency. So tell me again, what do case studies prove?"  

I don't think she appreciated my devastatingly awesome powers of deductive logic, and if you're wondering, no, we did not get hired. 

But your past doesn't have to limit your future. It might make it harder to achieve. It will definitely make both the decision and the initial pivot to a new direction far scarier. It may take longer to complete the pivot. And you may run out of resources before successfully securing your new future. But don't let your past limit your future. 

Recognize when you need to evolve because of an internal lack of desire, change in resources, or external forces in the marketplace. Or don't, and die. There is a reason only 52 of the original 1955 Fortune 500 companies are still on that list today. Make a plan, work the problems that inevitably will arise, and if necessary — pray — more on that later. 

Relationship Matter 

It turns out it IS who you know that matters. You still have to have a brain. And the folks with bigger brains tend to be more successful, but relationships fuel longevity, especially business longevity. 

The trouble is the human brain can only effectively manage about 150 concurrent relationships. It's called Dunbar's Number. Other scientists have delved into the topic producing their own relationship limits. But even those scientific studies put the maximum relationship number somewhere between Dunbar's 150 and 336 concurrent relationships. 

When you consider your immediate and extended family, friends, and coworkers all factor into that number, you start to run out of relationship room fast. Add in a healthy dose of social media networking, and you quickly have more relationships than you can, biologically speaking, manage. 

So what's an entrepreneur to do? 

Invest in technology — specifically a good CRM like Nimble or if you want a bit more power under the cranium, a marketing automation platform like SharpSpring (the one I use) to create your very own memory vault. Use these tools to create excuses to reconnect with the essential people in your life. But go beyond the simple birthday or anniversary reminder. Use tags to remember what's important to each person. Then when you come across an item they'd find interesting, you can quickly and easily share it with them. Often you'll get a short thanks for thinking of me message. But other times, it will instigate a conversation that converts to a customer or client or a referral. 

Believe In Something Bigger Than Yourself

If you're been around these parts for a bit, you've heard me talk about this point before. Whether you believe in God, Allah, Brahman, or maybe you prefer Buddhism — so much of what happens to us as entrepreneurs is outside our control. I recently heard someone say, "Change isn't a way of life... it is life." 

Isn't that the truth!

Every minute of every day, things change. And for most of them, the best you can hope for is to influence that change in your favor. There will be great gifts that befall you. There will be terrible hardships too. And in so many cases, your actions yesterday, today, or tomorrow will have nothing to do with creating either.

But in those darkest hours of the darkest days, believing in something bigger than yourself and giving yourself permission to let go of the feeling that you and only you can change the course of your future... well, that creates just enough emotional and spiritual space to breathe.  And that space might just save you


I recently had the opportunity to serve as the commencement ceremony speaker for my Goldman Sachs 10000 Small Businesses cohort. If you've never heard of the Goldman Sachs program and you're an entrepreneur, do yourself a favor and check it out. It's like a business incubator and an executive MBA program had a love child. Truly an amazing program. And best of all — it costs you NOTHING if you're accepted into a cohort.  

Now back to laughter. 😆

During my speech, I encouraged my fellow graduates to laugh because I believe that laughter is an essential part of surviving the entrepreneur’s journey

You're going to have days where you get to experience unimaginable highs when you're so excited, so happy, where things are going so well that you don't want to close your eyes and put your head on the pillow because you don't want it to end. And if you're honest with yourself, you’re afraid of what tomorrow may bring.

And there will be days where you don't want to open your eyes, much less lift your head off that pillow, because things are tough. Those days when things feel very dark, and you want to look up to the sky and scream, seriously God… there's nobody else to mess with today, nobody else you can pick on but me? Those are the days that will make you question whether you want to continue on the journey. Whether you want to continue with the struggle. 

That's where laughter can save you.

When things get so bad that you can’t see a way forward, laugh. Laugh until you cry. Because laughter isn’t just the best medicine, sometimes it’s the only medicine. So, laugh. Give yourself a few minutes to reconnect with your joy through laughter. Give yourself a few minutes to decompress, enjoy the little dopamine hit in the brain that recharges your batteries just enough to get back up, put one foot in front of the other, and continue your journey. Because while the journey is a struggle, there is beauty in that struggle

And that's it for this year, my friends. If you found something useful here and think maybe I might say something helpful again in the future, why not subscribe to my little bloggy thing to be notified of future missives? Don't worry, if after reading a few more articles you decide that I'm really not all that smart or funny — unsubscribe. No fuss. No muss. 

This post was originally published on Painless Prospecting, the weekly sales and marketing blog created by the fine folks at Converse Digital. If you want to learn how to create, engage in, and convert conversations into new clients and customers, give them a call

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