Sticking Your Neck Out: How Devin Sizemore Found Freedom, Fulfillment, and Massive Success Through Real Connections
“No one ends up on the top of Mount Everest by accident.” — Devin Sizemore
When you scroll through LinkedIn or Instagram, success often looks shiny, perfect, and effortless. Seven-figure businesses, tropical vacations, courtside seats. But beneath the highlight reel, many entrepreneurs are struggling, sacrificing their health, relationships, and identity in pursuit of “success.”
On a recent episode of Be the Giraffe, I sat down with my friend, entrepreneur, author, and master connector, Devin Sizemore, to explore what happens when you’re willing to stick your neck out, leave the herd, and redefine your life on your own terms.
And let me tell you—this conversation was raw, vulnerable, and incredibly powerful.
The Dark Side of “Success”
Devin’s story starts like many entrepreneurial tales: bootstrapping a business out of a small apartment, working 24/7, and scaling to become one of the biggest digital marketing agencies in the childcare space. By all external measures, he was winning.
Hundreds of clients
International team
Rapid growth
Seemingly glamorous lifestyle
But behind the scenes, Devin’s life was collapsing. His marriage fell apart. His health deteriorated. Despite running a seven-figure business, he was barely taking home a five-figure salary.
“The outside perception was that it was super successful. The company was successful, but I wasn’t.” — Devin Sizemore
Devin shared how his drive to please everyone—business partners, clients, family—led him to lose himself entirely. He was living a life shaped by others’ expectations rather than his own values and priorities.
The Wake-Up Call
For Devin, the turning point came through some harsh but necessary mentorship and self-reflection.
At just 23 or 24, a mentor challenged him with a question he’d never dared to consider:
“Why don’t you just sell the business?”
For Devin, his business was more than a livelihood—it was his identity. Letting go felt like tearing out a piece of himself. But in the end, he realized:
He was in love with his business, not with business itself.
His life was out of alignment with his true values.
Fifteen days later, he signed papers to sell the company. Within weeks, his marriage ended. The following 18 months were chaos—but also the beginning of freedom.
Rebuilding From the Ground Up
After the storm came clarity. Devin committed to a new path:
Health first. No more sacrificing his body for the business.
Family first. Being present for his daughter and building a balanced life.
Boundaries. No more one-way relationships.
Purposeful business. Building impact-driven ventures aligned with his values.
“Now, I wake up every day super comfortable, super content, and never worried about anything. That’s a crazy statement given the chaos I was in.” — Devin Sizemore
It wasn’t easy. There were lonely nights, financial uncertainty, and tough questions. But through it all, one thing sustained him: his network.
One Connection Away
Devin realized he wasn’t alone. The relationships he’d built over the years became his safety net. One friend provided him 21 nights in hotels after his divorce. Others helped him navigate career shifts and new ventures.
This inspired his book, Connection Expansion, and his system for helping others build transformative networks.
Here’s what Devin teaches:
Always add value. Don’t lead with sales—lead with service.
Control what you can control. Focus on your own actions, not outcomes you can’t dictate.
Never judge a connection. You never know who will open a door for you.
There’s value in every relationship. Even “small” connections can become life-changing.
Train by doing. Networking is a skill honed through real conversations and follow-ups.
“You’re one connection away from massive success in your life and business.” — Devin Sizemore
The Art of Real Conversations
One of Devin’s biggest secrets is simple—but rarely practiced: ask better questions.
Instead of diving into a sales pitch, Devin’s connection meetings follow a simple structure:
Where are you today?
How did you get here?
Where are you going?
What’s your biggest challenge?
How can I help?
This approach uncovers the real stories and real struggles people face. It creates bonds of trust that can open doors you never knew existed—internships, high-level partnerships, strategic deals, and lifelong friendships.
“Real people, real conversations, real connections.” — Devin Sizemore
From Mass Marketing to High-Impact Connections
Ironically, Devin started his career in digital marketing—chasing broad reach and mass audiences. Now, he focuses on deep, high-value relationships that yield exponential opportunities.
Instead of 10,000 shallow leads → nurture a few powerful connections.
Instead of chasing likes → cultivate real influence.
Instead of just building revenue → build a life aligned with your values.
Whether you’re a college kid looking for an internship or a seasoned CEO seeking your next big deal, Devin’s system works.
How You Can Stick Your Neck Out
If you’re stuck in a business or life that doesn’t fulfill you—or if you know there’s another level you’re capable of reaching—here’s Devin’s challenge:
✅ Recommit to yourself. Get crystal clear on your always and nevers.
✅ Audit your circle. Are you surrounded by people who truly support you—or just want something from you?
✅ Start real conversations. Ask better questions. Listen for what’s said—and what’s not said.
✅ Add value first. Show up with generosity and watch opportunities unfold.
✅ Be willing to walk through the valley. The way to a better life often runs straight through discomfort.
“No one falls up a mountain. You have to do the work.” — Devin Sizemore
Ready to Elevate Your Perspective?
Devin’s journey is proof that success isn’t just about money or fame—it’s about living a life of purpose, health, connection, and fulfillment.
If you’re ready to stick your neck out, be different, and create real impact, check out Devin’s resources:
[Connection Expansion (Book)] – Available on Amazon and audiobook.
Aces Connection Group – A community of givers and strategic connectors.
Work with Devin – Get guidance from someone who’s been there and found a better path.
Remember: you’re only one connection away from everything you want.
Be bold. Be curious. But most importantly, be patient.
Want to keep elevating your perspective? Subscribe to Be the Giraffe and join us next week for more stories of innovators who dared to stick their necks out and discover a better path.
P.S. If this episode resonated with you, you’ll love my Be the Giraffe book.
