M&A Advisor, Author, Entrepreneur - Sold Pepperjam to eBay; Raised tens of millions in VC; Help founders secure their legacy at legacyadvisors.io
Joined September 2007
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Why Most People Stay In the Same Place
I don’t think most people lack potential.
I think they stay where they are because they stay in familiar patterns.
Same routines.
Same thinking.
Same responses.
And nothing changes until those patterns change.
That’s the work.
Not learning more…
But doing something different. #pattern #personalgrowth #potential #change #personaldevelopment
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Why Some Deals Just Feel Better Than Others
Some deals just feel right.
And it’s not always because of the number.
It’s because there’s alignment.
The buyer understands the business.
There’s clarity around what happens next.
The expectations are realistic.
I’ve learned to pay attention to that feeling.
Because when everything is forced or unclear, it usually shows up later in the process. #clarity #expectations #alignment #ExitPlanning #exitstrategy
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Jun 13
What I Learned About Pressure
Pressure used to feel like something I needed to avoid.
Early on, it was uncomfortable.
But over time, I started to see it differently.
Pressure is just a signal.
It means something matters.
It means there’s growth on the other side.
And the more you operate in it…
the more normal it becomes. #personaldevelopment #personalgrowth #resilience #pressure #selfactualization
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Jun 13
What I Look for When a Founder Says They Want to Sell
When a founder tells me they’re thinking about selling, I’m not just looking at the business.
I’m looking at the founder.
Where are they mentally?
Are they energized? Or are they burned out?
Because that context matters.
Selling from a position of strength feels very different than selling from a position of fatigue.
And it usually leads to a very different outcome. #exitstrategy #exitplanning #founder #mindset #entrepreneur
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Jun 12
The First Time I Raised Capital
The first time I raised capital, I remember thinking—
this is going to solve everything.
More resources, more growth, more opportunity.
And it definitely helped.
But it also came with pressure.
Expectations.
Accountability in a different way.
That experience changed how I think about capital.
It’s a tool.
A powerful one—but only if the foundation of the business is already solid. #finance #venturecapital #entrepreneur #business #persistence
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Jun 11
The Danger of Waiting Too Long
I’ve seen this in business, and I’ve seen it in life.
People wait too long.
Wait for clarity.
Wait for confidence.
Wait for the perfect moment.
And the problem is—
That moment rarely comes.
At some point, you just have to move.
Make the decision.
And trust that you’ll figure it out as you go. #coldstart #momentum #action #motivation #personalgrowth
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Jun 11
Why I Don’t Get Too High or Too Low Anymore
Earlier in my career, I used to ride the highs and lows a lot more.
Big win? Felt incredible.
Bad month? Felt like everything was off track.
But after doing this for a long time, you start to realize—
both are temporary.
Markets change. Deals change. Businesses evolve.
So now, I try to stay a lot more even.
Because consistency in how you show up tends to matter more than any single result. #consistency #confidence #certainty #persistence #entrepreneur
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Jun 11
Check out my latest article: What I Learned Selling to a Public Company linkedin.com/pulse/what-i-le… via @LinkedIn
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Jun 11
Why State Control Changed Everything
This is something I underestimated early on—state.
Your emotional state.
Because I used to think performance was about strategy.
But I’ve seen too many situations where the strategy was fine…
and the state was off.
Frustration.
Doubt.
Overthinking.
And everything slows down.
Once I started managing my state first…
My decisions got better almost immediately. #confidence #EmotionalControl #personalgrowth #focus #decisionmaking
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Jun 11
The Long Game
Everything meaningful in my life came from playing the long game.
Building companies.
Investing.
Even relationships.
None of it happened quickly.
And that’s why most people don’t stick with it.
Because the results don’t show up right away.
But if you can stay consistent… stay focused… stay patient…
you separate yourself without even realizing it.
Because most people won’t. #focus #patience #Stamina #entrepreneur #persistence
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Jun 10
What Actually Builds Confidence
People think confidence comes first.
It doesn’t.
Confidence is a result.
It comes from doing hard things.
From keeping commitments to yourself.
From showing up when you don’t feel like it.
That’s how it’s built.
So if you’re waiting to feel confident before you take action…
you’ve got it backwards.
Take the action first.
Confidence follows. #entrepreneur #confidence #action #Persistence #businessgrowth
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The Early Days Nobody Sees
When I was building my first company, nobody was paying attention.
No press.
No recognition.
No validation.
Just long days trying to figure things out.
And looking back, I’m grateful for that.
Because it forced me to build discipline without needing attention.
And that’s important.
Because if you need validation to keep going…
It’s going to be a tough road. #entrepreneur #focus #ambition #Destiny #growthmindset
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The Power of Optionality
One of the biggest lessons I’ve learned in business is the power of optionality.
When you have options—you have leverage.
When you don’t—you take what you can get.
That applies to deals, partnerships, even your career.
The goal isn’t just to build something valuable.
It’s to build something that gives you choices.
Because the best decisions are made when you don’t have to say yes. #options #Optionality #choices #entrepreneur #growthmindset
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The Real Reason People Burn Out
Burnout isn’t always about working too hard.
I’ve worked hard for years.
What really causes burnout?
Working on something that doesn’t align.
Something you don’t believe in.
Something that drains you instead of challenges you.
That’s what wears people down.
So if you’re feeling burned out…
it might not be the hours.
It might be the direction. #burnout #focus #motivation #direction #passionate
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What Happens When You Raise Your Identity
There’s a point where you stop asking, ‘What should I do?’
And you start asking, ‘Who do I need to become?’
That shift changed everything for me.
Because when your identity rises—
Your habits follow.
Your decisions follow.
Your standards follow.
And you don’t have to force it as much.
You’re just operating at a different level. #decisionmaking #habits #standards #identity #PersonalGrowth
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What I Learned From Losing
Not every investment I’ve made worked out.
Not every decision I’ve made was right.
And early on, that used to bother me more than it should have.
But over time, I realized—
losing is part of the data.
Every mistake taught me something I wouldn’t have learned otherwise.
About people. About timing. About judgment.
So now, I don’t look at losses the same way.
I look at whether I learned from them. #venturecapital #investing #growthmindset #resilience #overcomingobstacles
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Why I Kept Going Back to Tony Robbins
I didn’t go to 14 Tony Robbins events by accident.
I went back because every time, I picked up something new.
Not always something massive.
Sometimes it was just a small shift.
A different way of thinking about a problem.
A reminder about standards.
A reset in how I was showing up.
And what I realized over time is—
Growth isn’t one breakthrough.
It’s a series of small adjustments…
that eventually change everything. #personalgrowth #DecisionMaking #tonyrobbins #dedicated #Strategy
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After 25 years of building companies, investing, going through exits…
here’s what I can tell you about growth.
It’s not fast.
It’s not linear.
And it’s definitely not easy.
But it’s consistent.
It’s showing up when you don’t feel like it.
Making decisions when things are unclear.
Staying in it longer than most people.
That’s really what it comes down to. #decisionmaking #persistence #PersonalGrowth #personaldevelopment #strategy
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Why I Bet on Founders
When I invest today, I’m not just investing in ideas.
I’m betting on people.
Because I’ve seen average ideas turn into great businesses…
with the right founder behind them.
And I’ve seen great ideas go nowhere…
because the founder couldn’t execute.
So when I meet someone, I’m looking for things you can’t fake—
resilience, ownership, consistency.
Because that’s what actually builds companies. #resilience #ownership #consistency #venturecapital #growthmindset
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