Digital Entrepreneur's Toolkit

Whew! Here we are! It's the final episode of Season 1.

I have to be honest: launching this first season of The Digital Entrepreneur's Toolkit has not been a cake walk.

Due to some goings on on the person side of things, my energy has been low and my focus has been fuzzy. It's been a rough fall. My goal was to push this beautiful podcast baby across the finish line before the end of the year and I am really proud to have done so.

Times of struggle give us the opportunity to learn more about ourselves. For that opportunity, I am grateful but I am also really looking forward to coming to a full stop here at the end of the year.

If Season 1 is The One About Community, Season 2 will be The One About Systems.

I'm looking forward to charging up my batteries so that we can come back better than ever in 2025 and share even more inspiring entrepreneur success stories with you in the new year - and beyond!

Whether we're having a chat on a podcast, hanging at a Disney park, or just catching up on the phone, you better believe my biz bestie Jen Hoffman dishes up some of the best mindset advice you've ever heard.

And it comes from a deep-seated desire to support her own growth, move that learning into action, and share what she's found with others.

Whether she's teaching restorative exercises or mindset magic, Jen is an exceptional teacher. I've learned so much from her and alongside her - and for that I am so grateful.

I hope you enjoy this episode!

Almost immediately after Jo and I turned off the microphone at the end of our recorded conversation that you heard in the last episode, she remembered something she wished she had said.

In discussing getting involved with volunteer work, she wanted to encourage folks to just start. To reach out and get started before it feels comfortable.

I don't know about you, but I need this reminder on the regular. I am highly allergic to failing in front of people. And I don't think I'm unique in that. Ice Queen Elsa notwithstanding, most people have a bit of an aversion to leaping into the unknown.

But if you want to share your gifts with others and use those gifts to benefit those who may be in need of what it is you have to offer, you have to step up and step out and start sharing.

But there's a little distinction that I've learned to make that has made tipping into action a bit less daunting and that is creating habits around measuring my leading inputs rather than my lagging outputs.

I hope this helps you too because - whether there's a course you'd like to launch or a book you're desperate to write or volunteer work you'd like to do - it requires you to become proactive.

Leading inputs will help support you in just that.

Lucky. That's the word that races to mind whenever I remember that I get to call Josephine Lauren my friend. And that I've been so lucky for 20+ years is wild to me.

Aren't we both still in high school? How did this happen?

But, like beautiful grape vines, we are aging in style and getting even better and more deeply rooted each and every year.

Jo is a child sexual abuse survivor and activist. And her generous spirit and bend towards community and collaboration is awe-inspiring.

If you've never met her, I'm so thrilled to introduce you and genuinely hope that you will follow and support her work at IncestAware.org and JosephineAnne.com.

Truth be told, I'm a bit nervous about sharing this episode. I've learned that, when I feel this way, it usually points to 2 things for me:

1. It's an indication that I care deeply about the issue.
2. It's time to ship it so I can invite other voices into the conversation.

When I'm stewing on a topic, I can become a bit obsessive and introverted. I tend to curl myself around the issue at hand, as though my isolated study will provide the pressure and polishing needed to turn to an amorphous chunk of mental carbon into a precisely chiseled diamond ready to be shared with the world.

But that's not really the way of things, is it?

I find my ideas become more nuanced when I engage in informed, thoughtful conversation around them with others.

So here's my request of you, friend.

Will you listen to this episode then consider joining the conversation?

If yes, please head to laurengaggioli.com. I'm turning on the comments for this episode and I will also be linking all of the resources I mention - particularly those of Amy Webb.

This topic is far too important for us not to have a chat about it. I would love to hear your position on A.I. and how you're thoughtfully deploying it or why you're opting out.

I'm looking forward to hearing your thoughts.

Join the conversation @ laurengaggioli.com/digital-entrepreneurs-toolkit/beigification-of-information-ecological-impact-ai/

One of my very favorite parts of hosting a podcast is having people on that I've had the pleasure of knowing for years and hearing them tell their story from the very beginning.

Paul Gowder and I have been friends for nearly a decade now. We met through a mastermind led by this season's first guest, Lou Mongello, and have attended numerous conferences together.

We've spent more hours chatting over leisurely dinners and after-dinner bourbons than I can count.

I consider his friendship is a true treasure.

And, yet, for all that time together, we've rarely have a linear conversation! (That might've been the bourbon's fault!)

So here we are, diving into the past and learning how Paul, a dedicated civil servant by day, ended up creating PowWows.com: one of the most informative websites on the internet for anyone looking to learn more about Native American culture.

By indulging his curious nature and taking the next right step over and over again, Paul created a thriving online community and built an online business long before every entrepreneur was aiming to do just that.

I'm excited for you to listen and be inspired by one of the nicest and smartest guys you could ever hope to meet.

I adore Stranger Things.

And this should come as no surprise because, if you know me, you probably also know that I adore the Steph(v)ens: King and Spielberg, of course.

My dad read me Firestarter when I was 10 and gifted me his copy of The Gunslinger, all 7 tomes, that sit beside my first edition Harry Potters on my bookshelf. My mom took me to see Hook in the theaters when I was 7 and brought Duel home from Blockbuster when I was home sick in middle school.

When we took a family vacation to Nantucket, we took the ferry to Martha's Vineyard for a day just to do the Jaws tour.

I have spent countless hours under the Steph(v)ens' spell. I feel like their storytelling magic is baked into my DNA at this point.

So why on earth did it take 3 full viewings of Stranger Things to pinpoint one particular moment very early on that set the stage for Steven fans everywhere to feel as cozy in Hawkins as they are on Amity Island?

(Let's be honest: Stephen fans were hooked from the jump by the font, the music, and episodes being titled "Chapters".)

The answer is, of course, that the Duffer Brothers are masters of the art of honoring.

And there's a very important Easter egg in here for all of us who are looking for a takeaway to apply to our businesses. It's one that can shift our owner's mindset profoundly and give us permission to custom tailor how we do business to fit into the larger vision of how we wish to live our lives.

We can get waylaid by all the shoulds and good ideas around us. We can end up feeling small and unworthy, constantly behind the 8 ball of all the things we feel we're supposed to be doing.

But the truth is that you don't need a bigger boat. You can do whatever you want because you're the chief of...well, probably not the police...but definitely your own company.

The Duffer Brothers offer us a masterclass in homage and a permission slip to buck the trends and cultivate your own originality while still standing on the shoulders of giants.

I hope the lesson here helps you root deep into what matters most to you and create your business on your own terms.

Conference kismet. That's what brought Amy Traugh and I together. I am so happy that our mutual friend Lindsay Dollinger leaned down our row at PodFest and said "You two definitely need to meet."

And meet we did, after the entrepreneurial conference, on a Zoom call and it was instant admiration from my side.

As an accidental, serial entrepreneur, Amy runs a tight ship. And, if you've been in the online entrepreneurship space for any amount of time, you know what a rarity that can be.

I myself am in the I-deliver-on-the-deliverables-for-my-clients-but-please-don't-look-at-my-internal-processes camp, so I say this without malice for those of us who feel a bit...shall we say...underbaked. I can always use an extra 15 minutes in the oven. ;)

But the thing I really love about Amy is, even with pragmatism and organization on her side, she hasn't cut off her intuition.

It's a balancing act. And Amy is an exemplary fellow entrepreneur for us to learn from.

Enjoy!

Today's episode is inspired by How To Lose A Guy In 10 Days and Andie's gift of a love fern to Ben.

When he nearly kills the fern through a complete lack of attention, she goes into over-the-top theatrical hysterics, asking "Are you gonna let us die?"

How many of us entrepreneurs are letting parts of ourselves die in (alleged) service of our businesses? How many of us put our most joyful and restorative past times on a shelf so that we can focus on our online business or side hustle?

::sheepishly raises hand::

I am 100% guilty of having done this.

• Launching a business is hard work.
• Maintaining flow in an existing business is hard work.
• Finding time to do all the things that just plain old adulting requires is (you guessed it!) hard work.

But I also know that, if I don't carve out time for me, literally nobody else is going to do that. Life and work will gobble up any time I'm hoping to have left over for myself.

As Oliver Burkeman reminds us in one of my all-time favorite books, 4,000 Weeks: Time Management for Mortals: “The day will never arrive when you finally have everything under control—when the flood of emails has been contained; when your to-do lists have stopped getting longer; when you’re meeting all your obligations at work and in your home life; when nobody’s angry with you for missing a deadline or dropping the ball; and when the fully optimized person you’ve become can turn, at long last, to the things life is really supposed to be about. Let’s start by admitting defeat: none of this is ever going to happen.”

Our full selves deserve better than leftover shreds of time and settling for slivers of ever-shrinking margins.

The real win is that, when we take time to roll around in something that is genuinely restorative, our lives and our work become infinitely better.

So consider the hobby or activity that you've shelved in an effort towards streamlined productivity and pull it back down off the shelf today.

A counterintuitive cosmic wonder is that you just might find that your work becomes more joyful and productive for the respite your reclaimed hobby gives you - in spite of the extra time it takes to really enjoy it.

A Few Resources Mentioned

Here's the article I mentioned: My Brain Is Itchy & There's No Cream For That

Here's the episode in which my friend Erik Fisher and I discuss taking restorative action: Practical Productivity For The Modern Parent

And here's the free mini course about naming your values: laurengaggioli.com/values

It is my great joy to share with you a conversation with my digital content strategy client and owner of my very favorite local yarn store in the Puget Sound area, Mr. Benjamin Bentler.

As is true of so many entrepreneurs, Ben is no one trick pony. He is highly motivated, incredibly productive, and juggles a lot across his myriad businesses.

(Did I mention he's also my voice teacher? There's nothing this guy doesn't do.)

I find people like Ben incredibly inspiring. They make me feel less alone in the chaos and I hope his wisdom that he shares from the trenches of his many businesses helps you on your journey as well.

And - remember - if you need support as you traverse the tricky landscape of the online business world, I'm just a phone call away!

With my Phone-A-Friend Business Mastermind, you can schedule time for us to check in and work on your entrepreneurial mindset and online business strategy @ laurengaggioli.com/mastermind.

We meet most Mondays and Thursdays. Each 60-minute call is limited to just 4 entrepreneurs, so you're guaranteed plenty of time to talk through your challenges and receive feedback. Plus, there's no long-term commitment required and your first session is just $25 when you use the discount code FRIEND at checkout.

Click here to register for your first virtual mastermind call today.

See ya real soon!