Jim Barnish Jr.

Dragonfly Operating Partners

DragonflyOP works directly with high-growth, venture-backed startups to bridge the gap between growth potential and outcomes. Startups often struggle with scaling effectively, navigating operational complexity and positioning themselves for successful funding rounds or exits. 

My role is to lead a talented team of startup to scale-up executives that are embedded alongside founders, providing hands-on leadership to accelerate growth and drive measurable business outcomes in all go-to-market, product and operational functions from pre-seed stage through Series C:

- AI-Driven Strategy
- Go-to-Market Strategy
- Marketing and Messaging
- RevOps and Sales Playbooks
- M&A and Investment Strategy
- Pricing and Packaging Strategy
- Product Launches & Management
- Organizational Design & Strategic Planning
- Product-Market Fit and Customer Validation
- Channel Partners and Direct Sales Management

DM me to learn more

Managing Partner

O.R. TRAX

Board Member

Chattr

Strategic Advisor

Emobi

Florida Funders

I support deal flow processes and relationships with the founders of Florida Funders' portfolio companies, home of the #1 active VC in the state of Florida. 

My other company, Dragonfly Operating Partners (DragonflyOP) is a Strategic Partner to Florida Funders, working with the fund and its portfolio to increase IRR.

Partner

The Dirt

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:
- Apple Podcast: https://podcasts.apple.com/us/podcast/the-dirt/id1612094562
- Spotify: https://open.spotify.com/show/16dOKv7C5g1A3ZLIUnE4mT

Podcast Host

Orchid Black

* SOLD MAJORITY STAKE TO EXISTING AND NEW STRATEGIC PARTNERS *

As Founder and Managing Partner, I built a team of skilled operators serving bootstrapped businesses, Private Equity and Enterprises eyeing carve-outs. I left to connect my roots (VC) and high-growth skillset, starting a similar firm (Dragonfly Operating Partners) down-market focused on seed stage through series B companies, partnering with the VC firms that invested in them to accelerate growth and increase IRR.

Orchid Black maximizes your company's value and positions you as a tech-forward business for upcoming liquidity events. We use data-driven analysis led by a team of seasoned growth experts to optimize your product offering, accelerate your revenue, and execute a tailored roadmap to transform companies into the most valuable versions of themselves.

Founder & Managing Partner

ThumbStopper®

StartUp Solutions

* ACQUIRED BY MORGAN HILL CAPITAL PARTNERS (MHCP) *

• Served more than 25 startups in a performance-based equity incentive model to drive successful GROWTH outcomes for early stage technology companies looking to raise capital, evaluate buy/sell M&A opportunities or just plain grow organically via revitalized sales and marketing efforts.

• Led an end-to-end direct/channel go-to-market strategy shift for a PE-backed product company. Key deliverables included strategic plan, packaging and pricing of solutions, channel partner program and financial model including a resourcing plan and key performance indicators (KPIs).

CEO / Founder

Synapse

Synapse Florida is a Non-Profit Organization purpose-built to help Florida's Entrepreneurial and innovation ecosystems thrive.

Board Member & Director of Exhibitors

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 $1.5B in value creation.

→ 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.

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:
- Apple Podcast: https://podcasts.apple.com/us/podcast/the-dirt/id1612094562
- Spotify: https://open.spotify.com/show/16dOKv7C5g1A3ZLIUnE4mT
- Google Podcast: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5idXp6c3Byb3V0LmNvbS8xOTE0MDM4LnJzcw==
- Amazon: https://music.amazon.com/podcasts/a2a092df-1038-4517-a01e-4486bcd55607/the-dirt?refMarker=null&

A decade of grit. A year of transformation. And this week, a huge moment for O.R. TRAX. We’ve officially been acquired; and the story (and buyer) behind this one matter.

Abram Liverio and Todd St. Louis built the company in an unglamorous way. 

Deep expertise. 
Relentless improvement. 
Steady focus.

Quiet, consistent execution inside hospital ops long before “workflow automation” became a buzzword.

But the last 18 months have been different.
This team didn’t just grow. They scaled with intention.

They brought in me and my team to help profitably scale.

They tightened the product.
They sharpened the go-to-market.
They rebuilt internal systems.
They delivered execution every quarter.

And that’s why this acquisition matters.

This wasn’t hype. This wasn’t luck.
This was operational excellence meeting strategic fit.

And Banyan Software was the right buyer.

Not just because they’re disciplined.
Not just because they know how to scale niche category leaders.

But because they share the same values that built O.R. TRAX in the first place: humility, long-term stewardship, respect for customers, and a belief in doing things the right way.

Banyan was a great partner throughout the process. Steady. Aligned. Respectful of the mission and the people. The kind of buyer you hope for but rarely get.

They saw what we saw up close:

- A category-leading platform trusted by health systems

- A service culture that sets the bar

- A business with fundamentals you rarely see in healthcare IT

- A team with the hunger to keep leveling up

From my seat, it’s been a privilege to run shoulder-to-shoulder with this group: refining the commercial engine, building repeatable sales motions, shaping the product narrative, tightening the funnel, and hitting benchmark unit economics week after week. Month after month.

It’s one thing to want to win.
It’s another to do the work.
And it’s even better when you do it with good souls and strong values behind the scenes.

This next chapter with Banyan gives OR TRAX the reach and resources to accelerate the mission: making operating rooms more efficient, safer, and easier to coordinate for everyone involved.

Massive congrats to the entire team.
Massive respect for the discipline, the people, and the heart that got them here.

The best chapters get written after an outcome like this.

🚀

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.

Ok I’ve been thinking a lot about Thanksgiving.
Not the food or the football.
The gratitude part.

The part founders usually lose when they start chasing whatever shiny thing promises a hockey-stick graph.

I say this with humility because I’ve lived it. 

I  rebranded my first startup three times in 18 months.

In another I launched 11 pilots at once, burned millions and never fully shipped a single one (eek).

My favorite was the time I pivoted business models five years in a row and wondered why people didn’t have full clarity on the great work I did.

Different companies.
Same root problem: I forgot to be thankful for the plan I already had.

Thankfulness isn’t fluffy.
It’s discipline.

It’s choosing to value the work you committed to — even when early data scares you and every LinkedIn post makes you feel behind.

This quarter it’s “We need AI.”
Last quarter it was PLG.
Before that it was a new vertical.

Founders call it “innovation.”
Most of the time it’s fear.

👉 The Project Graveyard
Twelve “priority” projects 50% complete.
Millions spent.
Zero compounded.

👉 Brand Confusion
Internally: “new era” every month.
Externally: “We don’t trust you’ll stay in this market.”

👉 Team Cynicism
After the fourth “big initiative,” the team stopped believing anything would last long enough to matter.

The hidden truth:

Most companies aren’t failing because of bad strategy.
 
They’re failing because they don’t stick with one long enough to win.

Getting ready for Thanksgiving, watching my kids steal snacks off each other’s plates, it hit me:

The founders who are winning aren’t the ones chasing novelty.

They’re the ones practicing gratitude for the focus they already chose.

One CEO I admire has a rule:
- Three strategic priorities per year.
- One that gets most of the energy.
- Everything else goes to backlog.

They hit goals four straight years.
Because they did less — fully.

Startups don’t die from starvation.
They die from indigestion.
Too many projects.
Too many resets.
Too many stolen snacks.

Not enough nourishment for the work that mattered.

This season, be thankful enough to focus.
Thankful enough to finish.
Thankful enough to ignore the shiny idea.
Thankful enough to honor the right idea.

Because the companies that win aren’t the ones with the most ideas.

They’re the ones with the most impactful follow-through. 
🙏

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Three founders. 
Three very different hiring decisions.
One identical outcome: chaos.

Founder A hired a “10x engineer.” Built v1 fast. Also tanked morale, alienated peers, and created a bottleneck. The code shipped. The culture died.

Founder B kept a loyal but underperforming leader. Execution slowed. High performers quit. The team’s output cratered because one person never carried their weight.

Founder C rapidly hired 20 people to “scale.” Wrong expectations, wrong mindset, wrong culture. Most were gone within months along with salary burn and operational drag.

Three stories.
One truth: every early hire is a DNA drop.
Hire wrong, and consequences compound.

Founders love to blame “product issues,” “timing,” or “execution.”

But the root cause is simple: a hiring issue.

A wrong hire at 10 people causes damage you won’t feel until 30 or 50… usually after your best PM or engineer walks out the door.

Studies show disharmony and bad team dynamics are top failure reasons for startups - not lack of vision.

What did the founders learn the hard way?

👉 The brilliant jerk isn’t brilliant. They produce code and destroy collaboration.

 👉 The loyal-but-underperforming leader isn’t “family.” They’re an anchor.

 👉 Hyper-scaling without clarity isn’t growth. It’s chaos.

The cost of a bad hire isn’t just salary; it’s the ripple: lost productivity, lost trust, lost culture, lost momentum.

To replace an EE costs 50-200% of salary.
The real cost is time.
The rarest asset in an early-stage startup.

Whats the remedy? Rigor. Discipline. Clarity.
Define values before hiring. 
Hire slow. Fire fast. Cliché because it’s true.

Early-stage? Don’t chase narrow specialists.
Chase people who say, “I’ll figure it out.”
Chase curiosity, ownership, integrity.

A cohesive team will beat a dysfunctional “superstar” team every time.

The right investors know this. 
They bet on teams, not products.

When someone bets on yours…

Are they betting on a foxhole-ready unit or a loose collection of individuals?

Startups are battles. 
Build a team you want w/ you in the trenches

If you get people right, almost everything else becomes solvable.

If you get them wrong, nothing else matters.

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