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 founder came to me convinced they had a sales problem. Revenue was flat. Pipeline slowing. Deals dragging.

But after ten minutes in the books, it wasn’t a sales issue - it was a runway issue.

They were running the business like a car on fumes, flooring the gas.

Another blamed the “tough fundraising environment.”

But their expenses had tripled in twelve months on things that didn’t move revenue.

Different stories. Same root cause.
Not bad markets. Not bad ideas.
Just a gap between ambition and discipline.

At Dragonfly Operating Partners, we see this every quarter.
Founders chase motion over progress.
VCs cheer growth, then flinch when burn doubles.

Everyone talks “runway” but few actually measure it.

Running out of cash isn’t the disease.
It’s the symptom.

You get there because you:

💡 Hire for the company you want, not the one you have.

🔍 Budget for best-case scenarios instead of real ones.

⚙️ Scale before you’ve nailed the model.

🧭 Assume more money is always around the corner.

The fix isn’t complicated - it’s consistency.
Know your numbers cold.
Check burn weekly, not quarterly.

Ask “what if we miss?” before spending like you won’t.

VCs, this applies to us too.
We reward confidence and momentum.
But we should value clarity more.

The best operators we’ve backed know their financials like pilots know altitude - they can’t afford not to.

When cash runs out, time runs out.

And time is the only real advantage anyone has in this game.

Growth matters. Vision matters.
But discipline is what keeps both alive.

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.

Forty hit different this year.

At thirty, I threw a huge party.
At thirty five, same story.
Loud nights. Packed rooms. Zero brakes.

Forty came with something bigger.
Friends flew into Tampa. 
Not for noise. For presence. 
For time that actually meant something.

We loved. We talked. We laughed about the old days. We dug into life, business, purpose, growth. It felt like oxygen.

And then came the best gift of my life.
My second son.
Born days before my birthday.

Nothing compares to that moment.
It sharpened everything. 
Two kids now. 
Two reasons to build with intention. 

Two reasons to stop wasting minutes on things that do not matter.

Starting a new company at forty hits the same way.

You cut noise.
You cut excuses.
You build what matters and you drop the rest.

This year taught me one simple truth:

Go for it.
The idea.
The move.
The pitch.
The call.
The risk.
Go for it.

Not recklessly.
With clarity.
With intention.
With purpose.

I used to overthink everything. Timing. Opinions. Judgment. All the mental static. But every meaningful moment in my life happened when I stepped in anyway.

If you are sitting on something right now, move. One step is enough to start. Perfect timing is a myth. Progress is built in motion.

I am stepping into this decade with real gratitude.

For my wife.
For my kids.
For friends who show up.

For family who drops everything to be part of the moment.

For my team and clients Dragonfly Operating Partners who build with purpose and accountability.

Forty is not a finish line.
It is alignment.
Faith. Family. Purpose. Growth. Direction.

If you needed a sign to take your shot, this is it.

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Alarm at 5:35. Celsius at 5:37. Quiet house count: 1 sleepless wife, 2 sleeping boys, 2 snoring dogs, 0 excuses.

Daily plan has 3 lines: ship, sell, show up.

By 6:30 I have 1 team update drafted, 3 social posts queued, 11 replies to a prospects and customers, and exactly 15 minutes left before the first small human alarm.

“Dada.”
Game on. Bottles, cars, the missing binky that statistically accounts for 9 out of 10 morning delays.

At 6:59 I am half CEO, half sherpa, carrying a laptop, a teddy, and the kind of optimism you cannot buy. Then gym and prayers for the needy (me).

At 7:59, I am on Zoom. Camera on. Heart rate at 92.

We review a 6 week roadmap in 16 minutes.

Three choices on the table:
1. Push a features / GTM list that looks good in a deck
2. Push a narrative that closes the gap in our funnel by 30%
3. Push our luck

We kill 2 features, tighten 1 headline, and agree to measure time to value in days, not weeks. The right kind of subtraction.

11:15 AM. Slack tally: 71 messages, 23 action items, 1 unsolicited opinion about our logo that no one asked for. A text from my wife with a photo worth more than every KPI on my screen.

2:00 PM. A founder friend pings me. They are at 18 months runway and 19 months of ideas. We swap notes. We trade honesty at a ratio of 1 to 1.

4:15 PM. The hard thing. We decide not to chase a whale that would have eaten 40 percent of our quarter. It hurts. It is also the first decision today that feels like a deposit into the future.

5:55 PM. Laptop closed. Kitchen open. Family dinner.

7:57 PM. Lights dim. Family prayers. Small hands grab my face like it is the only handle in the world. The line I never skip, not on a board call, not on a deadline, not on a day that felt like three days.

“Give James and Anthony big kisses from daddy. Love you. Big prayers. Amen.”

8:01 PM. Inbox shows 47 unread.
Zero of them matter more than what just happened.
But... I reopen the laptop for another couple hours.

9:35 PM. I write this for the future me who will forget how today felt and only remember whether the line went up. Then I spend more time with my wife.

Here are the numbers that actually counted.
2 boys hugged.
1 partner seen and loved.
3 decisions that moved the business.
0 moments traded that I cannot get back.

People say LinkedIn rewards confidence.
I think it rewards the truth.
The truth is I am building at 100 percent and improvising at 100 percent, often in the same hour.

If you are a builder who is also a partner and a parent, you already know the cheat code.

You can be tired at 10 and still be proud at 10:01.
You can carry a P&L in one arm and a toddler in the other.
You can run a company and still make bedtime by single digits 5 nights out of 7.

The story is not “we grew 300 percent.”

The story is “we chose alignment over adrenaline 3 times today and still read a book about dinosaurs twice.”

Huge milestone for the team at Chattr and a defining moment for the hourly hiring market.

Chattr has officially joined forces with UKG, one of the most powerful and respected names in workforce technology. For those who know the space, this is more than an acquisition — it’s a signal.

UKG isn’t just a large player. They’re a category anchor with the scale, customer base, and distribution power to set the tone for how people systems evolve. Their move into conversational hiring and automation through Chattr changes the competitive landscape overnight.

For years, competitors in frontline hiring tech have been building bolt-on chat tools, partial integrations, or “AI assistants” that stop at the application stage. Chattr went deeper — embedding into workflows, driving measurable conversion lift, and shortening time-to-hire for the biggest brands in retail, QSR, healthcare, S&D and manufacturing.

Now, with UKG’s reach behind it, that capability scales across tens of thousands of employers and millions of hourly workers. It’s not just another product integration — it’s a platform play.

From where we sit at Dragonfly Operating Partners , this is the blueprint for how tech-forward operators win in constrained markets:

1. Start with a real customer pain point.
2. Build tech that drives hard ROI.
3. Prove it with growth, retention, and efficiency.

Then align with a strategic powerhouse that can scale impact globally.

UKG saw what others are now scrambling to respond to — automation that actually works in the frontline hiring trenches.

Proud of Jim Schimpf Michael Nordberg Skip Marshall and the entire Chattr team. They built a company with Tampa roots and national reach, and now they’re part of a platform that will redefine how the world hires.

This isn’t just a great exit story for the team and its shareholders (shout out Florida Funders, Circadian Ventures BIP Capital) — it’s a wake-up call for everyone competing in the next era of workforce tech.

More details about the acquisition in the press release linked below.

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. 
🙏

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.

Funding is flowing again. But not evenly.
There’s a strange split in the market now.
Here comes the juice...

On one side, billions are being deployed into AI and “workforce transformation.”

On the other, great businesses - profitable, growing, and solving real problems - can’t get a term sheet to save their lives.

It’s not a capital shortage. It’s a filtering phase.

VCs are flush with money but allergic to risk without narrative.

LPs are cautious, funds are fighting for allocation, and suddenly everyone’s due-diligence process looks like an interrogation.

The irony?
The startups most likely to survive this cycle are the ones least willing to play the game.

I talk to founders every week who’ve built $1M to $20M revenue machines with clean books, efficient growth, and real customers, but they’re getting overlooked because their deck isn’t dripping with AI glitter or “category creation.”

Meanwhile, someone else raises $15M with a prototype and a buzzword-laden vision statement.

That’s not efficiency. That’s confusion disguised as conviction.

Here’s what’s working in this market:

📚Precision storytelling. You don’t need hype. You need clarity.
 
🏦Clean financials. The story’s real when the math agrees.

📈A defined view of market timing. Don’t say “AI.” Say why now matters.

💵Intentional frugality. Efficiency is the new credibility.

Here’s what’s dead:

“We’re adding AI to our onboarding flow.”
 
“We just need cash to unlock scale.”
 
“We’ll figure out monetization later.”

Fundraising today isn’t about selling potential; it’s about defending clarity.

I happen to see it up close, and am in the midst of my 7th exit this year (with clarity-driven businesses).
 
The best founders we work with don’t chase funding first. They chase control, precision, and leverage. They build companies investors have to fund, not ones they hope to.

To the VCs reading this - the opportunity right now isn’t in the shiny stuff. It’s in the disciplined operators hiding in plain sight. The founders who know their unit economics better than their pitch deck. The ones whose NRR and CAC ratios actually compound.

To the founders - your advantage isn’t the trend. It’s the traction you can prove with a spreadsheet, not a slogan.

Funding is flowing. But it’s not for everyone.

It’s for the ones who’ve learned that clarity, not capital, is the real currency.

(End rant)

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