Deeper Business

Build your business - and your business-building intuition with foundational frameworks and practical application.

Jun 08 • 5 min read

Third Time's a Charm


Relationship Rhythms is open for enrollment!

Thank you for joining the waitlist, so you're the first to join! FYI, Deeper Business & Cohort Members get a 10% discount.

Code: DBMEMBERS

I’m on my way to Boise for Craft and Commerce as you read this… if you’ll be there let me know!


When many of us think about live networking events or conferences, we imagine a fast track to new clients, partnerships, or even a whole new audience.

“How many business cards should I bring?”

“What’s my pitch or opt-in offer?”

“Can I sell from the stage?”

But relationships—the kind that actually build your business—don’t work that way.

Let me back up.

In April of 2023, I joined a community of creators called The Lab. And when I joined, people were registering for Craft and Commerce, a conference for creators, but I didn’t go. I had other plans with my husband in New York that weekend, and honestly, I didn’t think it was that important. After all, who needs to go to a conference for an email platform?

What I didn’t realize then was that it wasn’t just a conference. It was where so many of the relationships I saw flourishing online were getting their start.

After that first conference, I felt real FOMO.

I’d see photos, hear stories about group dinners, late-night chats, masterminds forming—relationships that seemed to shape entire businesses and opportunities. But I didn’t even know who I was missing, because I hadn’t met them yet.

Over that first year in The Lab, I started recognizing names. I participated in the forums, saw the same faces in Zoom chats, joined their newsletters, and bought some of their programs. Slowly, it started to feel less like I was on the outside looking in.

When Craft and Commerce came around in 2024, I decided to go.

But I didn’t just show up—I’d been building small connections all year. So when I arrived, I already had a conference group: Lab mates who welcomed me into conversations. I didn’t feel alone, wondering whose table to sit at like in high school. I met creators whose names had been familiar for months, and suddenly they were real people.

But here’s what really surprised me: the magic didn’t happen at the conference. Sure, I met some incredible people—like Hollie, who did the illustrations for my brand. But that client relationship didn’t start in one conversation. I’d already seen Hollie’s work online. I was looking forward to meeting her IRL. That conference moment was just the catalyst—a reminder that there was a person behind the profile photo.

For my third year in 2025?

I’m mostly excited to see the friends I’ve been building relationships with throughout the year. Colleagues who've been on my podcast, people I’ve bumped into from other events, my friends who I'm sharing lodging with, people whose work I started following because I met them over the past two years.

I’m not worried about what I’ll get out of the conference.

(I’m sure the keynotes will be fine, but that’s not why I go.)

Instead I’m asking:

  • Who can I deepen my relationship with?
  • How can I support the people I’ve been in touch with all year?
  • Where can I give instead of just get?

Because relationships aren’t built in a single conference—or even just at the conference itself. They’re built in the in-between: the emails, the collaborations, the small acts of support that make you more than just another face in the crowd.

The support that makes showing up to the next year even sweeter.

Here’s what I wish someone had told me before my first conference:

  • Don’t expect too much from a single trip. You probably won’t meet your next best client over dinner.
  • But you might meet the person who introduces you to them a year later.
  • Start before you arrive. Find out where your people are gathering and show up for them.
  • And afterward? Send that email. Comment on their posts, respond to their newsletters. Keep the conversation going.
  • Focus on a few relationships you can really invest in. The fastest way to build trust is to show up consistently for a small group, not scatter yourself too thin.
  • Be open for surprises. You very well might meet your next client, or your next collaborator. That after dinner drinks that you’re tempted to skip might lead to the best conversation you’ve had all trip.

So when you head to your next conference, skip the “one-and-done” mentality and imagine you’re planting seeds—deeply, because doing it in a human-to-human capacity—that need to be tended over time.

And if you’re curious how to play that long game intentionally, Relationship Rhythms opens tomorrow: my program designed to help you build trust-based connections that actually stick.

NEW EPISODES

More money from existing clients (without the sleazy "ascension" value ladder)

If you need 2-3 new clients per month... forever... to make your business profitable, I hope you have a marketing machine or a host of referral partners.

But if you don't, watch this video about authentic ways to extend the value and relationships with your clients without being trapped in a business model you don't want or withholding transformation until someone buys your high-ticket program.

A Framework-Free Life Update and AI fun

In this riffy, delightfully unstructured episode, we ditch the outlines, frameworks, and “polished” content in favor of a real-life check-in, some AI trivia, and a sneak peek at my summer program.

We also get real about our own partnership: the messy business of joint ventures, what happens when your business is in a different gear than your friend’s, and how to talk about money and collaboration in a way that feels human.

And because she couldn’t resist, Meg quizzes Jessica on AI trivia—highlighting the joys, the contradictions, and the occasional panic about what AI knows, what it doesn’t, and how we’re using (and refusing) it in our own businesses.

UPCOMING EVENTS

June's Dialogue: Radical Rest for Entrepeneurs

June 18, 12 pm ET

Radical Rest for Entrepreneurs is an experiential gathering hosted by Maegan Megginson, founder of Deeply Rested, designed to help you break free from burnout, release the pressure of perfectionism, and build a business that supports you as much as you support everyone else.

​In this workshop, you’ll explore the seven types of rest and uncover exactly where you need the most support.

Community and Reads

The Lifestyle Business Playbook of 2025 | Tropical MBA

Is the “lifestyle business” still alive in 2025?

Dan chats with longtime friend Jeff Pecaro about the evolution of internet business, what today’s solopreneurs get right (and wrong), and how constraints can lead to clarity. (I personally loved the evolution of market maturity and what trends have come in and out of favor).


Why 90% of Dan Koe followers never make money.

Dan Koe is responsible for pulling over 50,000 (idk probably more) people into the "Creator Economy" with the dream of becoming profitable creators.
Look around Twitter and you'll find an entirely saturated market of people trying to teach how to do the same as he did.
But there's one big problem. Almost none of Dan's followers end up making money. And most of them quit less than six months into the journey.
What gives? Why does Dan make a ton of money pursuing his interests, while his followers can't seem to make a dime?

Jessica Lackey

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Build your business - and your business-building intuition with foundational frameworks and practical application.


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