Find Your “Freedom Number” + Grow Your Audience Without Chasing the Algorithm (with Jackie Dragone)
Meet Jackie Dragone
Jackie Dragone is a business coach who works primarily with female entrepreneurs in years 0–4 to help them build, grow, and scale a business that’s rooted in strategy—and actually makes money.
She’s the founder of The Pink Business Club, and she recently launched The Pink Business Club Podcast, where she showcases women doing the dang thing while teaching the mindset and strategy needed to build a sustainable business.
Jackie’s mission is clear:
Help women find their “freedom number” so they don’t have to answer to anyone else.
What Is a “Freedom Number”?
When Lindsay asked Jackie what she meant by “freedom number,” Jackie explained it in a way that instantly clicked:
Your freedom number is the amount of money you want to make that creates real freedom in your life.
Not just a random revenue goal—but a number connected to:
- not needing another job,
- taking time off when you want,
- traveling if that’s your thing,
- supporting your family,
- building savings,
- investing,
- breathing again.
And here’s the key: your number will look different than everyone else’s. For one woman, freedom might be $5,000/month. For another, it might be $50,000/month. The point is alignment—building offers, pricing, and capacity that can actually support that goal.
Business Is Simple… But Not Easy
One of Jackie’s most grounding reminders in this conversation:
Business is actually really simple. It’s not easy, but it’s simple.
She broke it down like this:
- Get clear on who you serve
- Know the problem you solve and the transformation you offer
- Craft strong messaging
- Create consistent visibility
- Learn how to market and sell
- Run the offer
- Repeat
It’s not about reinventing the wheel every month—it’s about getting clear, getting visible, and repeating what works.
Audience Growth That Doesn’t Depend on “Going Viral”
Jackie’s approach to audience growth is refreshing because it’s not rooted in “more followers = more money.”
Instead, she focuses on connecting with and nurturing the right people—and building a community that lives beyond the algorithm.
Strategy #1: Host a free training or free class
Jackie shared that free trainings are one of her favorite ways to pull people out of “silent watching mode.”
Why it works:
- People who never comment will sign up
- You demonstrate your value in a real-time way
- You move people from “Instagram content” to “I trust her”
Bonus: They join your email list, which means you’re no longer relying on social media to reach them.
Strategy #2: Run a “market research” giveaway for a call
Another strategy Jackie swears by is offering a chance to win a coaching call in exchange for market research answers.
It does a few powerful things at once:
- Helps you understand your audience deeply
- Identifies hot leads fast
- Creates instant connection and trust
Jackie shared that when she did this, every person she connected with ended up buying from her eventually—some at a low-ticket level, and others becoming full-time clients later.
Her point: It’s not just “grow your audience.” It’s maximize relationships with the people already closest to you.
Why You Should Always Lead People Off Social Media
Jackie dropped a truth bomb that every entrepreneur needs to hear:
If your only strategy is posting content and then dropping an offer… you’re probably leaving money on the table.
Because the algorithm might show your content again… or it might not.
Instead, she encourages entrepreneurs to create ways for people to opt-in:
- a free Facebook group
- an email list
- a free class
- a challenge
- a downloadable freebie
That way, you’re building a real community you can actually reach.
How Jackie Grew Her Email List (and Turned It Into a Membership)
Jackie grew her email list through a simple, consistent strategy:
She hosted a free weekly call every Wednesday at 1PM for a year and a half.
People had to join her list to attend—so it became a natural funnel into her community. Over time, she transitioned that free call into a paid membership:
The Pink Business Club Membership
- $47/month
- weekly coaching + community
- designed to make coaching accessible
And the results? Jackie shared that within the first two weeks, she had 27 members—because she had already built trust through service and consistency.
No pushback. No drama. Just a natural next step.
Her Podcast: The Pink Business Club
Jackie launched The Pink Business Club Podcast on April 1, 2023—which also happened to be her 40th birthday (iconic).
Her goal with the podcast is to:
- provide real value
- amplify women who are building successful businesses
- remind listeners that success requires perseverance
- normalize discomfort as part of the process
As Jackie shared, the difference between people who succeed and people who quit often comes down to one thing:
Your ability to sit in the discomfort.
Jackie’s Social Strategy Right Now: Instagram + TikTok
Jackie also shared she’s been experimenting with two posts a day on Instagram (when life allows) and expanding to TikTok.
Her biggest takeaway?
It’s not just posting more—it’s also engaging more. Visibility increases when you’re interacting on the platform.
Her TikTok strategy:
Jackie is aiming for content that’s hyper specific, like:
- “How to double your revenue next month”
- “3 steps to increase saves”
- “How to lose 10 pounds without giving up pizza” (example from the coaching world)
The more specific, the better—especially on TikTok.
From Health Coach to Business Coach: Jackie’s Pivot Story
Before coaching entrepreneurs, Jackie built a long career in health and fitness—starting back around 2010. But the pivot happened when she realized her greatest gift wasn’t just coaching clients…
It was developing leaders and building businesses.
She shared that in nearly every job she had, she was promoted into leadership and was helping grow the company—onboarding coaches, training teams, building systems.
After Covid, she realized she wanted to go all-in on what she’d been doing all along:
building businesses and developing people.
Rapid Fire Highlights
At the end, Lindsay asked Jackie a few fun rapid-fire questions:
- Morning routine or night routine? Morning—quiet time before everyone else wakes up.
- Human design? Generator, 3/5 profile, sacral response.
- Current book? The Big Leap (and she wants to reread it!)
- Favorite vacation spot? Tulum, Mexico—she and her husband want to go back for two months.
Connect with Jackie + Lindsay
Connect with Jackie: https://www.jackiedragone.com
Connect with Lindsay: https://www.lindsaydollinger.com
Join the conversation in Lindsay’s free Facebook group: My Most Magical Me Movement
And if you loved this episode, screenshot it, share it to your IG Stories, and tag @lindsaydollinger so Lindsay can tell you thank you!
Now go create, own, and spread your magic. ✨