Business

  • August 14, 2025

    My D.A.D. Framework for Overwhelmed Solopreneurs

    One of my favorite lines in 30 Rock, a show full of one-liners, is uttered by Jack Donaghy, Alec Baldwin’s character:

    I’m the Sisyphus of Reaganing.

    Reaganing, in the show, is where you have a day where you make no mistakes. It’s the “perfect game” of business.

    It’s a deep joke. You need to know a little bit about US politics during that time. You also need to know who Sisyphus is.

    Sisyphus, if you don’t know, was condemned to pushing a boulder up a hill, just to have it roll back down, after a life of hubris in which he tried to cheat death.

    Futile labor, for all eternity.

    Don’t you kind of feel like that running a business sometimes?

    Read at Source

  • January 20, 2025

    Why You’re Losing Money when You Mow the Lawn

    If you’re in the northeast United States, you know you need to mow pretty much every week in the summer. But there was a point a few summers ago, due to rain, lack of child care, and travel, that I didn’t get mow my lawn for nearly 3 weeks.

    So one day, I set out to mow the very long, still kind of wet lawn. On top of that, I had to weed wack, and take a hedge trimmer to some overgrown bushes. It was shaping up to be a big job. Something that normally takes an hour took an entire afternoon.

    And because I was choosing yard work over billable work for my business, I lost income.

    That was the last time I mowed my lawn.

    Read at Source

  • January 5, 2025

    Changing Direction with my Newsletter in 2025

    I had a friend who would always announce they’re “about” to do “something,” without ever saying what it was. But before they did it, they’d announce something different, repeating the cycle of announcing and never doing.

    They’d just be thrashing, hoping to find something that worked before it even had a shot at working.

    Every so often I worry I do this — change directions too often, before a strategy can really take root to determine if it works.

    But I’m conflicted because I also don’t want to keep doing the same thing if it’s not working.

    In reflecting on 2024, I realized that I’ve done a poor job at positioning myself in a way that I can truly help solopreneurs who have podcasts.

    Part of it is that I was thrashing a little bit. I was offering too many products and services that fit the bill of, “Sure, I can help you” vs. “This is the thing I really want to be known for.”

    This worked out OK for my bottom line, but inhibited my growth.

  • October 13, 2023

    What CaboPress has to do with Cartography

    Recently I found myself thinking about early Cartographers and how they managed to create accurate maps. They’d use rudimentary tools, landmarks, and their own observations.

    In-fact, distances were often estimates due to lack of accurate measuring tools. That caused a lot of problems for travelers, would rely on those distances and measurements to get to where they wanted to go.

    As we know today, being slightly off over a long distance could land you in a dramatically different place. Just ask Christopher Columbus.

    Today, of-course, we don’t have that problem. With most of the world mapped out, and those maps accessible at any moment with real time directions, accurate maps are commonplace. Modern cartographers are focused on creating advanced, interactive digital maps.

    It’s not that simple when you’re starting your own business. Sure, you might have a rudimentary map. But there’s no set of directions you can follow to have a successful business…despite what Twitter bros tell you.

    That’s why you need a great cartographer for your business — someone (or a group of someones) who can use their observations and experience to help you create the map that will get you to where you need to be in your business.

    Chris Lema, CaboPress, and all the great people I’ve connected with there have been those cartographers for me.

  • October 10, 2022

    CaboPress 2022: The Best One

    It has been 3 years since I’ve been to CaboPress. The last event I attended was in 2019, it was canceled in 2020, and we were less than 2 months away from my daughter’s due date in 2021.

    Needless to say, I was excited to go back. Each time I attended, I came home energized and implemented something to help my business grow.

    I really needed it this year. But before we get to all that, I want to do a quick recap of years past.

  • June 21, 2022

    How My Toddler Taught Me to Sell Results not Features

    Truly wonderful, the mind of a child is.

    Yoda, Star Wars: Attack of the Clones

    That quote is from Master Yoda, as he’s trying to help Obi-Wan Kenobi try to find a missing planet. Obi-Wan let his assumption (“that’s impossible because only Jedi can access this data”) get in the way of the actual answer — which was given to him by a young Padawan.

    Similarly, my son Louis, who’s 2 and can only say a few words and sentences, helped reinforce a very important sales lesson for me:

    Don’t sell features. Sell the results.

    See, I was trying to get my son to abandon the wide-open world of the front yard (and active road), for the safer, albeit less exciting back yard. First, I ask my son if he wanted to go to the backyard (or the platform/product). He said no. What can the backyard offer him that the front yard can’t?

    So then I ask if he wanted to go on the trampoline (a unique feature of the platform). Again, he said no. Perhaps he didn’t realize what the trampoline was, or what it can do for him.

    Finally, I asked him if he wanted to bounce (the results of using the feature), and he said yes.

    Don’t sell your product or service by talking about features (or worse, how you made it). Sell what your product or services can do for your customers.

  • June 9, 2022

    Validate an Idea With an Email Form

    If you’re anything like me, you get super excited about an idea and want to build it right away. But I’m here to tell you that’s not the best way to spend your precious time.

    Spend some time validating an idea so you don’t waste time executing a bad one. I know this from experience.

    “Oh, it shouldn’t take too long to code this project…probably just a weekend.” Then you actually have to market it.

    But if you were only willing to spend two days making it, how much time are you actually willing to spend marketing it?

    IF you really want to scratch that itch, don’t spend a weekend. Spend an hour setting up a presale form. Presell the product (course, ebook, whatever). Actual money is a great form of validation.

    Even if you want to presell at first, create an email list pitching the idea. “Sign up here to be the first to know.” Then you can spend your time nurturing that list, gathering feedback, and understanding if it’s something worth making.

    As Bill Gates said, you can always make more money. Time is the only thing you can’t get back. So spend it wisely.

  • June 6, 2022

    Cost is More Than Just the Money Out of Your Pocket

    One of the most enduring lessons in my life comes from a high school Accounting class1 where we learned about opportunity cost. It’s the potential loss you’ll experience when choosing one thing over another.

    The concrete example from the class was that if we choose to go to a concert on a Friday night instead of working, the opportunity cost is the wages we’d make. And if we’re paying for the concert out of pocket, it’s lost wages + the cost of going to the concert.

    When it comes to out-of-pocket expenses, choosing to go to a concert, or on a vacation, instead of working might be an easier choice for many adults. Those are expenses we don’t mind paying.

    But what about when it’s money we don’t want to spend vs. some positive outcome?

  • April 20, 2022

    How My Eye Doctor Got Me to Happily Pay More (with a Good Offer)

    I’m up for my annual optometry appointment, which I without fail make at the exact time my contact prescription expires. See, I wait until the last minute because I don’t like getting dilated. It’s not that I’m afraid of the dilation. But usually, I’m going on a workday and dilation really cuts into my schedule; right now I’m a stay-at-home dad for half the week, so workdays are coveted and rare.

    While booking the appointment, I asked the receptionist if I needed to get dilated. I know the answer is yes because it is my first appointment with them since being diagnosed with Type 2 Diabetes, which can affect eyesight. I said my preference if I don’t need it, was to skip it.

    She told me I did need to get the back of my eyes checked. They could do the dilation for free, and I’d have blurred up-close vision for 4-6 hours. Or for $39, they could do a digital photo of the back of the eye, which doesn’t affect my vision at all.

    Guess how quickly I said yes to the photo.