Jim Barnish Jr.

Over the last two decades, I played a key role in growing & selling dozens of B2B software & tech-enabled businesses. 

In all, I've driven more than $1.7B in value creation and played a pivotal role in 12x exits.

→ 15x growth of a tech-enabled distribution business from $40M to $600M revenue. Now > $1B :)
→ Guided a 55% increase in exit value (from $23M to $36M) FinTech company in < 7 months.
→ Created B2B tech investment engine at the most active VC in Florida. 3 funds & even more exits.
→ Led the turnaround & sale of a Series B enterprise cloud business.
→ Acquired, integrated & grew 30+ companies ranging from $2M-$250M in Enterprise Value.

But, all of this success came with many failures too.

→ Growth stalling at $5M, $20M, $50M. 
→ Spending all of my time working "IN" the business, but not "ON" the business.
→ Churn increasing & competition passing me by.
→ Ineffective strategies, teams, products, operations.
→ Deciding to sell the business, but being told my valuation much less than I expected.

You name it. I failed at it. 

Regardless of where the failures stemmed from, I knew there was an opportunity to make each business worth a lot more, but I rarely knew what to do next - often leaving me quite "stuck" & burnt out!

Each time, I dreamed of the perfect business growth partnership to guide me into success.

→ Diagnose what was needed to grow and exit.
→ Put together a strategic roadmap on how to make it happen.
→ Help execute, since everyone is hands-on in a growth-stage tech business.
→ Bet on themselves (and me) by aligning their compensation to my business' performance.

But, I could never find the partner that met the above criteria.

So, I tried to do it internally. Or hired traditional management consultants.

Both led to wasted capital, time and most importantly, less growth & profitability.

So, with the vision to offer founders what I only dreamed of accessing as an operator & owner, I created several companies (Dragonfly Operating Partners, Orchid Black and Startup Solutions) hiring others just like (and better than) me. Together, we guide B2B SaaS, Enterprise Software & tech-enabled businesses to scalable, predictable growth & maximum exit value.

The results for founders, VCs and other investors have been incredible! 

And for my team, since we align our compensation to our results.

If you want to learn more about business growth & exits, DM me.

Podcast Host

This business podcast is a place where we get down into the depths of a founder's story and expertise. Being an entrepreneur isn't easy; it's painful, it's ugly, it's dirty and it usually entails things that people don't want to hear. This show is meant to bring forward the trials and tribulations that entrepreneurs have encountered and overcome.

Listen on Your Favorite Platform:
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Jim Jr.

2025 was the 1st year of building DragonflyOP, and it’s been the most aligned and fruitful year of my professional life. Not because it was easy.

Not because everything worked perfectly.

But because we were clear about what mattered from day one.

Before DragonflyOP, I built numerous software businesses, and most recently two services at both ends of the spectrum.

Both were successful in their own ways. One for pre/early revenue businesses and the other for companies over $20M.

But both revealed a massive gap the market still hadn’t solved.

Investors in the middle need better returns.
Founders in the middle need less theory.
Neither needs slides or output.

They need real operators, fully accountable, in the trenches.

That gap is now solved with DragonflyOP.

Our success this year came from a few very deliberate focus points.

FOUNDATION
From day one, God was at the center.
Not as branding. As the reason.
Stewardship over ego. 
Service over shortcuts.

ALIGNMENT
We built DragonflyOP with partners and operators who share the same values, urgency, and definition of success. High-caliber people. Real experience. Real exits. Still hands-on. No spectators. Everyone works.

OWNERSHIP
We don’t hide behind titles or outsource accountability. We own the number. We build from the number. And our incentives are aligned with those outcomes.

PRECISION
Clear filters on who we serve.
Clear standards for how we operate.
And a repeatable system for value creation.

NOW.. Along the way, we also learned some things the hard way…

☝️Uncoachable founders don’t work, no matter how big the opportunity looks.

✌️Being selective about both clients and investor partners isn’t optional if you want real outcomes.

Because of these principles, our Value Creation Blueprint (VCB) methodology scaled to new heights this year, right alongside the companies we serve.

The results our team drove speak for themselves:
➜ 32 happy, growing clients
➜ 7 successful exits
➜ Revenue 14x of Yr 1 in my last business
➜ Deep, trust-based relationships with some of the highest-caliber founders, operators, and investors we’ve worked with.

All driven by referrals.
Investor-led. Portfolio-deep.
Built on trust, not transactions.

As the year turns to ‘26, I’m deeply grateful.
Grateful to God for clarity and peace.
Grateful for my family for patience and ❤️
Grateful for our team that live the life.

Grateful for the founders and investors who trusted us early.

Dragonfly is still early.
But it’s built on the right things.

Faith over fear.
Alignment over ego.
Ownership over optics.
Execution over stories.
Outcomes over output.

And we’re just getting started.

Partnering with VCs to increase IRR 🏆 Helping founders find the best way to grow, profit & exit (with max value) & make fewer dumb mistakes in the process. Growth or get out.

Two weeks into the year, I’ve already caught myself doing something familiar. Looking back at the intentions I set before the year got noisy.

Before calendars filled.
Before momentum showed up.
Before it became tempting to confuse motion with progress.

Not goals.
Not resolutions.

Intentions.

And even this early, a few things are already clear.

⓵ First:
This FEELS like it has the makings of a great year.

Not because results are in.
But because the inputs are right.

The work is focused.
The conversations are honest.
The decisions feel grounded instead of reactive.

⓶ Second:
God is at the center of it.

Not as a slogan.
Not as a performance.

But as a steady reference point when the obvious move isn’t the right one.

Already, there have been moments where speed was available…but patience felt wiser.

Moments where a quick win was possible…but restraint protected something bigger.

Moments where ego wanted to act…but faith asked me to wait.

⓷ Third:
(keeps proving true no matter the season)

The year will rise or fall on whether the right leadership team is in place for this stage.

Not the flashiest resumes.
Not the loudest operators.

But people whose strengths cover my blind spots instead of competing with them.

That kind of leverage compounds quietly.

It reminded me of something I read recently about someone making an AI system dramatically smarter…not by adding horsepower, but by changing how it was guided, constrained, and prompted.

That’s leadership.

Not doing more.
Not pushing harder.

Designing the system so better outcomes become inevitable.

That’s how good years are built.

You don’t brute-force them.
You architect them.

With faith.
With the right people.
With humility about what season you’re actually in.

So two weeks in, I’m not asking:
“How do I grow faster?”

I’m asking:
“How do I stay aligned while growing?”

Because when alignment is right, progress tends to take care of itself.

End stop.

Huge opportunity to learn from and partner with a stellar founder and CEO!

Tarpon Springs, Florida, United States (Remote)

Founder’s Associate Intern (Chief of Staff Track)

As a results-driven leader in enterprise sales and business transformation, I specialize in driving revenue growth, optimizing marketing strategies, and aligning sales with technology-led solutions. With over two decades of experience in B2B sales, I have successfully led high-impact initiatives that improve operational efficiency, increase profitability, and enhance business scalability.

I excel in developing data-driven demand generation strategies, leveraging cutting-edge tools like Salesforce, Marketo, and ABM platforms to drive measurable outcomes. My expertise spans multiple industries, including manufacturing, private equity, and technology, where I have built and executed go-to-market strategies that deliver tangible business value.

Key Achievements:

Accelerated Demand Generation – Increased pipeline growth by 275% at Armanino LLP by deploying targeted digital marketing and sales enablement strategies.

Market Expansion & Partnerships – Led a Go-To-Market strategy at Clockwork.ai that secured partnerships with the top 200 U.S. accounting firms, driving new revenue streams.

Revenue Growth & Transformation – Generated over $4.5M in annual revenue at UHY Advisors by implementing strategic business development initiatives and SaaS solutions.

I thrive at the intersection of sales, marketing, and technology—partnering with C-suite executives to implement automation, improve EBITDA, and align business processes with long-term strategic goals. Whether scaling enterprise accounts or optimizing sales pipelines, my focus remains on delivering sustainable growth and transformation.

Let’s connect and discuss how I can help drive success for your organization.

Joseph Chivini

Tomorrow will feel a little different.

I was fortunate to know Virginia Halas McCaskey late in her life, and everything you ever heard about her was true. Quiet strength. Deep faith. Unwavering loyalty to family and team. 

She lived by a simple creed: Faith. Family. Football.

I’ll be rooting from the stands, wishing she were here to see this season — and especially this moment. The team honoring her with the patch means something. You can feel it. And for a playoff game against the Packers, it matters even more.

Here’s to playing the game the right way. With discipline, toughness, and respect for the legacy on that jersey.

#GoBears
#BearDown
#ChicagoBears
#football
National Football League (NFL) Chicago Bears

Director, Sales | B2B Growth & Partnerships | AI & Automation Advocate

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The Battle

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