She built a network that buys—without selling to strangers

In partnership with

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And Speaking of Entrepreneurs Doing Things Differently…

Jennifer Bennett isn’t just managing her business—she’s reinventing the way entrepreneurs connect, scale, and stay sane. She’s the founder of Get Desky and one of the best relationship-builders you’ll ever meet.

In this week’s feature, Jennifer shows us what it really looks like to lead with systems, serve with integrity, and build the kind of business that actually fits your life.

How Jennifer Bennett Manages Hundreds of Relationships Without Losing Her Mind (Or Her Weekend)

There are two kinds of entrepreneurs.

The first kind opens 15 browser tabs trying to find that one contact from that one podcast, then gives up and decides to “circle back” later. (They won’t.)

The second kind pulls up a beautifully segmented list, sends a message that doesn’t sound robotic, and moves on with their day.

Guess which kind Jennifer Bennett is?

Spoiler: She’s the second. But she used to be the first—until she got tired of tripping over her own spaghetti bowl of contacts, offers, and half-finished systems.

Now, she runs Get Desky, a company that exists to help other entrepreneurs stop duct-taping their backend together and start building something that works. For them, their team, and—importantly—their sanity.

The Spaghetti Bowl and the System

Jennifer has this great analogy. Most people’s businesses are like a giant bowl of spaghetti. Everything’s tangled. You know the pieces are in there, but if you had to explain them to someone else? Forget it.

So when people try to delegate, they end up just handing the whole bowl over. “Here, figure this out,” they say. (Usually to a poor unsuspecting VA.)

But delegation without a system isn’t delegation. It’s outsourcing your overwhelm.

Jennifer doesn’t just sort the spaghetti—she straightens the strands. One by one. Then she hands you back a workflow that makes sense, can be taught, and can be scaled. Or she builds the whole thing for you, which, let’s be honest, is what most people realize they want after about five minutes of trying to do it themselves.

Built for Connection, Not Chaos

Jennifer is one of those rare people who genuinely loves connecting with others—and is freakishly good at it. How does it not get overwhelming? She’s got process in her bones.

When she’s launching something new, like her Colorado networking retreat, she doesn’t cold-message 5,000 people she’s never met. She hand-selects 60 names from her network—people she knows, has spoken to, and who would actually want the thing she’s offering.

It’s not some magic list. It’s maintenance.

She’s built it by showing up, staying connected, and building systems that track who’s who and what matters to them. This is the stuff nobody tells you when you’re starting out. That the real business isn’t in the big flashy launch—it’s in the invisible threads you keep weaving, day after day.

Hustle-Free Is the Goal

Jennifer’s not anti-effort. She’ll work hard—just not in circles.

She’s seen what hustle culture does to people. The burnouts. The broken families. The health crashes and hollow wins. She’s not here for it.

Instead, she’s building something different. A business that fits around her life—not the other way around. Brings her co-founder mom and her kids to events. Refuses to let interns work unpaid. She’s not angling for a hustle badge. She’s making sustainable success look good.

And she’s helping others do the same.

Why Most People Don’t Follow Up (and She Does)

Let’s get honest for a second. Most entrepreneurs are good at meeting people. But following up? That’s where the whole thing goes off the rails.

You have a great conversation, make vague plans to connect again, and then it vanishes into the void. Not because you don’t care. But because you don’t have a process.

Jennifer does.

Her team knows what to say, when to say it, and how to keep the conversation alive. Even if it’s been months. Even if the lead didn’t convert right away. Even if they met at a random event three years ago. And because of that, her network doesn’t just grow—it activates.

People show up for her because she’s shown up for them. It sounds simple, but very few people actually do it.

Building Deeper, Not Louder

Jennifer’s success isn’t about being the loudest. It’s about being the most connected. She’s not trying to win at social media or go viral on command. She’d rather have a strong group of 100 that she can genuinely support than 10,000 silent followers watching from the sidelines.

And now? She’s creating spaces where other entrepreneurs can experience that kind of support, too.

That’s what long-term vision looks like.

She Doesn’t Want Your Free Labor (Seriously)

Let’s talk about something she said that deserves its own headline: Jennifer doesn’t believe in unpaid work.

Even when schools require internships to be unpaid, she opts out. “That goes against my values,” she says, plain and simple.

In a world where free labor is often seen as a rite of passage, she’s quietly rewriting the rules. Creating opportunities that don’t exploit. Building businesses that make space for life. Showing her kids—and everyone else—that it’s possible to do well by doing good.

What Happens When You Borrow Confidence

Jennifer’s team doesn’t have to show up perfect. They just have to show up willing. If they’re unsure, she says something simple: “Borrow mine.”

Borrow my confidence until yours kicks in.

That’s leadership. The kind that doesn’t need to flex. The kind that leaves people better than it found them.

And it’s one more reason why her clients don’t just get systems—they get belief. The belief that yes, this business can work. That yes, it can be simpler. That yes, you can have a life again.

Ready to Stop Managing Mayhem?

If your “system” is currently a stack of sticky notes and some vague hope that you’ll remember to follow up—Jennifer’s your person.

She’s not here to judge. She’s here to help you untangle the chaos and build something that won’t break the minute you look away.

You’ll get tools. You’ll get a team. And you’ll get a way of working that actually works for you.

Connect with Jennifer at https://socialselling.getdesky.com

So, You Got a Nasty Review... Here's What to Do Now
Date: Monday, May 5, 2025 at 9:30 a.m. Eastern

Got a review that stings? Whether you’re an Amazon seller, a coach, or a course creator, getting hit with a harsh review can feel personal—and tank your confidence fast.

Join me live in the Entrepreneurs Gone Wild Facebook group with international client strategy expert Anastasia Vladychynska as we talk about what to do next. We’ll cover:

• How to reframe the review (without reacting emotionally)

• What it might actually be telling you

• How to use it to improve—not implode

• And when to ignore it completely

Anastasia brings deep insight from working with brands like McDonald's, Hugo Boss, and MaxMara, and now helps experts retain 90% of their clients through exceptional experiences.

This is an honest, practical conversation for anyone who’s been on the receiving end of rough feedback—and wants to handle it like a pro.

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