Seth Yakatan

Raising & Selling 📈 $1B+ Raised 💰 22 Companies Sold 🤝

Are you struggling to communicate your vision to the capital gatekeepers?

Are you exploring selling your business but don’t know anything about:
✘ Due diligence
✘ Term sheets
✘ Earnouts

Friend, you're lucky you found me...

I'm Seth Yakatan.

I have 30-odd years experience as a corporate finance professional.

My specialties are:
💰 Raising money
🤝 Selling companies

And I’m f**king good at it.

I’ve raised over $1B and sold 22 businesses.

My career has mostly been supporting small-cap and major corporations seeking capital to grow, or
to find strategic acquirers.

Most of these companies are in: 
— biotech
— cannabis
— pharmaceuticals
— DTC consumer goods

I’ve been on boards, taken companies public, gone up against multinational corporations, raised from VC and PE funds.

All of it. 
Many times over.
Whatever your problem is, I’ve seen it before.

But let me level with you:

What I REALLY love is helping people to get to the finish line.

Talking to entrepreneurs excites me.

But in my experience, entrepreneurs are mostly s**t at raising capital and selling companies.

** They just don’t understand investors **

And that’s where I come in.

Together, we workshop: 
✔ Your pitch
✔ Your deck
✔ Your strategy 

And help you raise the capital to GROW and SELL your business.

If you need this help—and almost every business does—send me a DM.

Like, now.

Don't lose another potential investor or acquirer with the wrong pitch.

Seth ✌️

Co-Founder

Merchant Bank / Advisory / Family Office

Hate the three largest MSOs?? Well hate all you want, look at the numbers…

You’ll see that THEY ALL DELIVERED on Q4 2025 results.

Say what you want…the numbers DON’T LIE.


>> What Happened?

Trulieve delivers industry-leading adj. EBITDA margin of 35.8%. 
(Oh they also have $255.5M in cash!)

Green Thumb Industries (GTI) grows revenue and adj. EBITDA by 5% and 19%, respectively. 
(While reversing the gross margin slide and delivering GM of 52.7%.) 

Curaleaf grew revenue by 4.0% while beating adj. EBITDA estimates.
(All while lapping the FIELD with 65% y/o/y growth in Europe.)


>> Why Is It Important?

Kim has a war chest and is poised to dominate TX and PA.

Ben has cash, stock, and has grown margin DESPITE compression.

Boris is the world’s largest cannabis operator by market cap. PERIOD.


>> What Am I Watching?

Boris has made a jump into EU for growth, do Kim and Ben follow suit?

If 280e goes away, do Truelive and GTI see a big bump in price?

Which one of these three raises THE MOST equity the day after S3?


You know I have been critical of all three of these companies and CEOs.

Time for me to give a tip of the cap to all three for DELIVERING on RESULTS, period.

Say whatever you want about these MSOs…

The NUMBERS DON’T LIE.

Where will you find me this year ???

At an IgniteIt Cannabis thats where...


Taking some time to thank the whole squad there...
Elliot Lane
Patrick Lane
Jason Raznick

Appreciate ALL YOU DO...
CHI-TOWN IS COMING !!!!!

What is it that you "do" for work ???

Honestly I am not 100% sure what "I Do"

I am 
a therapist
a garbage man
a facilitator
But most of all

a truth teller...

Thanks to Rachel Wright, CPA, MST and VERDANT Strategies

Want a relationship ?

Start with a bank, I did...

Shout out to the whole team First Citizens Bank
And My ACE Diana A.

Need a place because you been thrown out of every other bank ?
Call her or DM me...

Thanks to the crew at Sweed for the video...

U.S. cannabis sales fell 3.1% in Jan. 2026 vs. Dec. 2025…

This was across 15 tracked markets.

The data shows us that demand didn’t collapse….

But momentum has softened.


>> What’s Happening?

January sales dropped 3.1% sequentially across 15 U.S. markets.

Yes, down from December, but UP 4.6% year-over-year.

So demand didn’t fall off a cliff.

Declines hit western markets and 8 Eastern markets

What we are seeing is a redistribution.


>> Why Is This Important?

This is what market maturity can look like.

We are now playing with price compression + market saturation.

Cannabis might be behaving like a real consumer category.

Real consumer categories don’t grow in straight lines.

Ask Alcohol…


>> What Am I Watching?

Does this make already scarce capital become even more scarce?

Solvency wins in markets like this, watch the balance sheet…

This is where M&A waves begin (and have begun): in slowdowns.


January 2026 was not a bad month.

January 2026 was a signal, if you are able to read it.

The industry is shifting from land grab…to capital discipline.

And historically?

That’s when consolidation begins.

Watch the balance sheets — not the headlines.

No alternative text description for this image

So you thought the labor unions were going to sit still? Well, the TEAMSTERS started being the TEAMSTERS.

Cresco Labs is going to template how unions are going to begin shaping the future of the sector.


>> What’s Happening?

Workers at a Cresco Labs’ store in have gone on strike!

The decided to unanimously walking out over wages, hours, and long-term stability.

And the employees ARE REPRESENTED by…..Teamsters Local 429.

Shocked? I’m not…


>> Why Is This Important?

Make no mistake, unions are still powerful.

Teamster-affiliated pension capital exceeds $100B.

1.3 million members…nah…1 in 10 workers is a Teamster.

Teamsters touch almost 20% of ALL CPG goods in the USA.


>> What Am I Watching?

The Brotherhood has be quietly showing up in the industry for 3+ years. Does this signal great action by the Union?

They have the power to make changes, force policy and provide capital. Does this put the National in a mood to make a move?

Teamsters move America. Will they organize in a way that shapes the future trajectory of the industry?


When organized labor starts demanding “middle-class careers” inside cannabis, we know we’re no longer in a “startup ecosystem.”

You are in an “industry.”

Make no mistake the Brotherhood has the power and $$$ to shape things.

Now we have to wait and see what they will do next.

The Booze guys keep telling me:

“Everything is OK” but…

THE DATA tells a completely different story.

What I’m reading is:

GEN Z ain’t DRINKING.


>> What’s Happening?

In 2025, Gen Z accounted for only 4 % of alcohol sales.

You read that right. FOUR PERCENT!

21% of the country only purchased 4% of the alcohol.

And they’re THE FUTURE.

This is WAYYYY smaller than any marketers and policymakers assumed.


>> Why Does This Matter?

Well…EVERY industry is betting on Gen Z driving massive consumption.

And that might be true for a lot of products, but absolutely not for alcohol.

So the question then becomes, if Gen Z ain’t showing up for alcohol, then WHERE ARE THEY?


>> What Am I Watching?

What is the actual spend by this demographic across alcohol AND c@nnabis?

What is driving the buying behavior of this group??

IS there a cross-category substitution occurring???


If Big Booze is telling me everything’s ok but the segment they NEED to drive growth is a ghost…

What does that mean for alcohol?

And what does it mean for the future of consumption in the US??

The times are a changin’!

Want the key to success ???

BE PROFITABLE (yes, it's that simple !)

Very few business that are PROFITABLE actually fail...

Crazy, I know...but I am Crazy...

Appreciate Rachel Wright, CPA, MST + The VERDANT Strategies crew

When in doubt about THC bevs, just copy whatever alcohol does…

Makes sense, right?

That’s what Missouri is doing…


>> What’s Happening?

Missouri lawmakers are evaluating new rules around hemp bevs.

Basically, treat it just like alcohol: 21+ age floor, excise taxes, structured compliance, and formal retail controls on where and how and when they can be sold.

Interesting…


>> Why Is This Important?

The free-for-all is over, McConnell saw to that.

Now regulators are making sure this is not a GREY AREA in their own state.

Public policy and public safety means real rules.

AND states are moving AHEAD of FEDERAL CLARITY…

Interesting indeed…


>> What Am I Watching?

Does the alcohol-style model becomes a template?

Potency, labeling, age restrictions, retail placement, and taxation?

IF federal shifts which products actually survive in this space?


This is early how “cannabis beverages” get folded into mainstream categories.

Novelty products, that’s one outcome.

Alcoholic beverages, that’s a market shift YOU need to watch…

Germany’s medical market is quickly GROWING UP!

Dont tell Kaiser Wilhelm.

For me, this is one of the most exciting markets globally. I’ll explain why.


>> What’s happening?

Germany is turbo-charging its domestic medical cannabis cultivation.

This is REAL production capacity coming online, inside Germany.

RESULT: fewer imports, fewer bottlenecks, cheaper AND more reliable supply.


>> Why Does This Matter?

Germany is no longer an “emerging cannabis market”.

Europe’s biggest nation is now building serious infrastructure.

That’s how markets become durable.

More importantly, that is when capital gets comfortable.


>> What Am I Watching?

When does domestic cultivation finally stabilize price and availability?

Which operators can ACTUALLY GROW? (’cause folks that AIN’T EASY…)

How quick does the MSO/LP story line move from “EU optionality” to “Germany”.


Germany is the biggest and most important medical cannabis market in Europe.

In fact, it’s the most important anywhere outside of North America.

And EVERYONE is watching it…

So…the AG of Ohio just sued 9 MSOs…

What??

Yep…9 MSOs.


>> What’s Happening?

The AG of Ohio just filed an anti-trust lawsuit against 9 MSOs for being a cartel.

Suit alleges they moved to (i) reduce product choice, (ii) exclude local operators
& (iii) keep prices artificially high.

Wait isn’t this the MSO 101 playbook? Or am I missing something?


>> Why Is This Important?

This moves to the core of operating cannabis retail.

Reciprocal supply agreements
Shared information
Shelf-space quotas

The suit says: “An industry-wide scheme designed to push small Ohio businesses out of the market.”

Wow…thats not good PERIOD.


>> What Am I Watching?

Not really sure how this plays out but it sure does not “feel” good…

Does M&A move from efficiency to exclusion? (Also not good)

Does this start to show up in EVERY state??


If this gets steam it could be a game changer.

Adjusting my models and grabbing popcorn.

So did you REALLY think the ban was about hemp??

No no no.

It was about ALCOHOL.

And now the numbers are in:


>> Whats Happening?

Alcohol is done watching hemp from the sidelines.

In Q4 2025 a bunch of companies files highlight lobbying disclosures tied to intoxicating hemp:

Moët Hennessy
Bacardi
Diageo
Brown-Forman
The HEINEKEN Company
Sazerac Company

Hmm….read the tea leaves and follow the money.


>> Why Does This Matter?

Lobbying is balance-sheet-based muscle memory for alcohol.

They have been doing it since 1950 and they are GOOD at it.

Make no mistake, the alcohol industry is acknowledging something BIG:

THAT intoxicating hemp is already part of the adult-use landscape.


>> What I Am I Watching?

Which alcohol players move from lobbying to minority investments?

Or does alcohol flex harder to push hemp off the shelves?

Can cannabis incumbents realize they were out gunned (and outspent)?


Not sure how this plays out but I am going to crack 10mg bev and grab the popcorn!

undefined undefined

Moët Hennessy

Bacardi

Diageo

Brown-Forman

The HEINEKEN Company

Sazerac Company

Little more love from the MJ BIZ scene...
Shout for Rectitude Partners LLC
and my man Nicholas Bowers

thanks to the squad at 

Fat Nugs Magazine
Puff Creative

for a great night....4 Grams...COMING!!!!!

Rectitude Partners LLC

Rectitude Partners - Global Cannabis Packaging & Vape Tech Experts

Fat Nugs Magazine

Puff Creative

Is this the FIRST MAJOR ON PREMISE shot fired for THC beverages??

WELCOME to the 2026 Stadium EXPERIENCE!

THC Drinks are coming soon to an ARENA NEAR YOU!


>> What’s Happening?

Chicago’s United Center just announced its serving hemp-derived THC drinks.

Concerts/Sporting events/Big shared moments.

In case you didn’t know, that’s alcohol’s home turf….

THC is showing up more and more, without asking ANYONE for permission.


>> Why Is This Important?

Booze vs. THC is not the point.

The point is THC is now competing for share of occasions.

Normalization comes from repetition in trusted environments.


>> What Am I Watching?

The first league, venue group, or national operator that treats THC beverages in the same way ?

Who puts up the first THC Beverage advert in a stadium? (Remember USC/ Cookies?)

What major sports/food/airport group jump in next ?


5 beers or 5 2MG THC Beverages??

Same night, VERY different morning

Hang 10 and hit the dispo??

Adult use cannabis may be coming to the Aloha State…


>> What’s Happening?

Hawaii lawmakers filed legislation that would put rec cannabis to voters in November 2026.

If passed by a two-thirds vote in both chambers, Hawaii voters would be asked whether to amend the state constitution to legalize adult-use cannabis.


>> Why Does This Matter?

Ballot initiatives are cool but they are NOT a guarantee.

This was not brought forth by the electorate but by elected officials…

Not sure this get traction or mahalo…


>> What Am I Watching?

Do MSOs even bother modeling Hawaii as a near-term market?

Is capital ready to fund something in one of the worlds largest tourist economies?

Do voters notice they’re being asked to decide a policy?


Feel like another version of Pele’s curse.

Cannabis style…I will just grab a shaved ice.

Guess who’s messin’ with Texas?? Cann, that’s who.

Cann is fixin’ to dominate the Lone Star State.

Here’s what’s going down:


>> What’s Happening?

Cann secured Texas distribution with Spec’s.

Spec’s, for those that don’t know, is THE LARGEST beverage retailer in Texas.

Full SKU set in one of the biggest alc retail channels in the USA.


>> Why Is This Important?

This is not a test, a dispensary, one franchisee gone rogue, or a limited run.

THC drinks are moving via mainstream beverage infrastructure.

Spec’s has 200+ doors statewide.

Say what you want, I AM seeing a distribution shift...


>> What Am I Watching?

What other brands can howdy on down to distribution?

What other retailers jump on board now that we have Target, Circle K and Spec’s?

Is there movement on the regulatory side in Texas? (Remember a few months ago they tried to BAN HEMP??)


Want to make sure we give a big congrats to the Cann Team!

Jake B. and Nick Fasano 👏 👏

Feels like Danny Stepper and the LA Libations team left their fingerprints all over here, cause this ain’t my first rodeo…

Want to LEARN MORE? Get your spurs to The Beverage Forum April 2026.

Cann

Changing the way people socialize!

Deep understanding of all things cannabis. From brand development, company structure, state expansion and financial complexities. I help organizations grow from the Black to the white

CEO & Co-Founder at L.A. Libations & Globestepper Productions

LA Libations

The Beverage Forum

When you fail 3 times, why not try for a 4th??

That’s what PA is doing right now as the state makes its FOURTH attempt at a move to Adult Use.

Sure, why not??


>> What’s Happening?

My guy Shapiro gave his fourth budget address.

Increasing overall spending by 6% without broad-based tax hikes.

Oh and he put adult-use BACK on the table…AGAIN.


>> Why Does This Matter?

PA is surrounded by NJ/NY/MD/OH, all of which are pumping REC.

The budget conversation shows how much $ PA is leaving on the table staying medical.

How ELSE can you spend more and NOT tax the general public?


>> What Am I Watching?

This is now #4. Can it REALLY HAPPEN this time?

What will be the policy tradeoffs if this happens? Who loses?

Is THIS a state surrounded by AU finally admitting leakage is a tax policy?


Adult-use didn’t magically reappear…

It reappeared because PA needs the $$$.

Politics and budgets are not based on morality…

Bet your butt they are based on COLD HARD CASH.

And AU seems like a magical cash machine.

Has someone actually cracked the code to S3?

Well, maybe…

Kazmira Pharmacy just announced the first licensed 503A compounding pharmacy in the U.S. dedicated to prescription-only, THC-free CBD.


>> What’s happening?

I’m no lawyer but under the current S3 regs this could be a category.

Take CBD off the wellness aisle and into clinical practice.

Legal, all 50-states with reimbursement?

Hmmmm…


>> Why Does This Matter?

Well, if they crack the distribution matrix problem this could be a thing.

Both anticipating tighter CBD/THC rules and making compliant medicine ahead of the compliance wave.

Seems like a product doctors can prescribe without standing in a dispensary…


>> What Am I Watching?

Do physicians now have a reason to get involved?

Do payers/HSA/FSA systems begin to reimburse and treat this like specialty pharma?

Do others adopt this model?


I know that cannabinoids BEHAVE like medicine…

But once payors get ready for this category to stop being treated like lifestyle products.

Think your business is HARD?

Try this:

1. Every state (and city) has a different set of rules

2. The Government taxes you at an exorbitant rate 

3.  Capital flow is weighted to larger and later-stage operators

4. There is very little capital to begin with...

Now tell me you product is not Federally legal...WELCOME TO C@NNABIS!!!!

Appreciate the love from Alex D. and the squad from The High Index for the spot!

CEO @ The High Index | Connecting people, data, and opportunity

The High Index

Everything's BIGGER in TEXAS? Well, Texas Original just bet the ranch.


>> What's Happening?

Texas Original just opened the largest medical cannabis facility in Texas.

They’re expanding cultivation and processing capacity to meet rising patient demand.

No change in law…no ballot initiative.

Just cash, concrete, steel, and CONFIDENCE.


>> Why Does This Matter?

Well son, you don't go build the largest facility inside one of the most restrictive medical programs in the country…

THIS is what early movers look like in medical states.

And might signal that regulators are comfortable enough to let serious operators scale.


>> What Am I Watching?

Does demand absorb this build?

Does the program allow for success?

Who’s the next operator is to break ground?


Texas ain't first.

It won't be loud.

But when it moves, it will move at TEXAS SCALE.


Cowboy UP y'all.

CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

Helping leaders of all shapes and sizes grow their teams and themselves. 

Every week I tackle management, operations & startup topics that are helping 200,000+ people become better leaders.

Scot’s Newsletter

Highland is a leadership accelerator & community for early-stage founders (seed, series A/B) to develop into world-class CEOs. If you're a founder/CEO, hit me up!

Founder & Chief Professor

A family office with wholly owned businesses, private investments, and property. Ripple, Hubble, FanDuel, CaseText and more.

Managing Director & Founder

After the merger of Classy and GoFundMe, I’ve taken on a strategic advisory role to the CEO & executive team. I remain a large shareholder in GoFundMe and a big believer in our joint vision.

Strategic Advisor, GoFundMe

Haskill Creek is a new type of self-care store. Imagine a healthier & modernized version of a Walgreens or CVS. Family owned business.

Albion Soccer Club is one of the top youth soccer franchises in the United States with over 10,000 players and hundreds of teams across the country.

Co-Owner

Skills: Agriculture · Food Systems · Board of Directors

Board Member

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

Founder & Chairman

Skills: Nonprofit Technology · Start-ups · Management · Product Management · SaaS · Leadership · Fundraising · Entrepreneurship · Startups · Product Development · Social Entrepreneurship · Software as a Service (SaaS) Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Classy is a SaaS giving platform that powers the fundraising of over 10,000 nonprofit organizations. Classy is a certified B-Corp, has a team of 300+ people and has raised over $5 billion for social good since 2011. CEO & Founder

CEO & Founder

In Classy’s earliest days, we hosted large scale fundraising events with the goal of connecting millennials with local nonprofits in the San Diego area. CEO & Founder (pre tech company)

CEO & Founder (pre tech company)

Since 1951, The Nature Conservancy has worked to protect the lands and waters on which all life depends. Grounded in science, TNC supports innovation, leadership, and communication for conservation success throughout the world.

Leadership Council Advisory Board

Street Soccer USA is a nonprofit who's mission is to improve health, education, and employment outcomes for the most disadvantaged Americans by using sports to transfer the skills necessary so that they can achieve these outcomes for themselves.

National Board of Directors

Team Rubicon unites the skills and experiences of military veterans with medical professionals to deploy vanguard teams that bridge the gap in disaster response.

For more than 100 years, military, government, and business leaders have turned to Booz Allen Hamilton to solve their most complex problems. As a consulting firm with experts in analytics, digital, engineering, and cyber, Booz Allen helps organizations transform.

Senior Consultant

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland • Avoid most advice, including my own.

This is where companies quietly fall apart:

Most founders inherit the CEO title before they have any idea what it actually requires. 

You start the company, you get the title. 

No one sits you down and explains what the job is supposed to look like. 

You have to be intentional about learning the role. 

It’s not the same as being a founder. 

Two very different things.

***
Learn what the role of a CEO actually looks like in my recent article (link in comments)

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here: https://lnkd.in/eXTwa8eH

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