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Why I Only Bet On Those Who Bet On Themselves
This exact week, three years ago, I sat in two very different meetings with two very different founders.
The first founder spent our entire lunch explaining why his startup wasn’t growing: The market timing wasn’t right. His investors weren’t giving him enough runway. His team wasn’t executing his vision properly. The economy was against him. By dessert, I had heard every possible reason why success was just out of reach — none of which had anything to do with him.
Three hours later, I met the second founder in her cramped office. Her startup was facing similar headwinds, but her response was radically different: “I underestimated the sales cycle length. My initial go-to-market strategy was wrong. I’m working on three specific changes to fix this.” No excuses, no blame-shifting — just ruthless ownership and clear-eyed assessment.
Guess which founder I’m betting on?
Here’s the thing about people who bet on themselves:
They don’t need the world to be perfect.
They don’t require ideal conditions.
They look at obstacles and see opportunities for growth.
When things go wrong (and things always go wrong), they don’t waste energy on blame — they focus on solutions.
I’ve spent the last decade investing in and working with entrepreneurs, and I’ve noticed a pattern so consistent it’s practically a law of nature: Success follows those who take ownership. Not sometimes. Not usually. Always.
Think about the most successful person you know personally. Not Elon Musk or Steve Jobs — someone you’ve actually observed up close. I bet they share this trait: When things go wrong, they look in the mirror first.
The world is filled with talented people. It’s bursting with great ideas. But talent and ideas are commodities. The truly rare element — the one thing I’ve learned to bet everything on — is the capacity for radical ownership.
Because here’s what I know for sure: In the long run, the person who owns their failures will outperform the genius who outsources blame.
Every. Single. Time.
Want proof?
Let me show you what radical ownership really looks like, and why it’s the only reliable predictor of success I’ve ever found…
The Ownership Divide: What Really Separates Winners from Almost-Weres
Let’s get specific about what betting on yourself actually means, because it’s not what most people think.
It’s not about confidence. I’ve met plenty of confident people who crumble at the first sign of failure.
It’s not about optimism — some of the best self-believers I know are pragmatic pessimists.
And it’s definitely not about taking credit when things go right.
Betting on yourself is about one thing: Taking radical ownership when things go wrong.
The Tale of Two VPs
Last year, I watched two VPs handle the same crisis: A major product launch that flopped spectacularly.
VP #1 had a ready arsenal of explanations:
“Marketing didn’t position it correctly”
“Engineering missed key features”
“The market wasn’t ready for innovation”
“Competitors played dirty”
Every explanation was plausible. Some were probably true. None were useful.
VP #2 took a different approach: “I missed important customer signals. I rushed the launch because I was too focused on hitting a date rather than hitting the mark. Here’s my plan to fix it.”
Same situation. Same level of talent. Radically different ownership levels.
Guess which VP turned things around within six months? Guess which one is now a successful CEO?
The Ownership Test
Want to spot someone who truly bets on themselves? Listen to how they tell their story. The ownership divide shows up in language:
Non-Owners say:
“They didn’t give me enough resources”
“No one told me about the deadline”
“The client was impossible to work with”
“The market conditions weren’t right”
Owners say:
“I didn’t secure enough resources”
“I failed to clarify the deadline”
“I couldn’t find a way to make the client successful”
“I misread the market conditions”
Notice the pattern? It’s not about taking blame for everything that goes wrong. It’s about taking ownership of your response to what goes wrong.
The Price of Ownership (And Why Most Won’t Pay It)
Here’s why true ownership is rare: It’s painful.
It requires you to embrace uncomfortable truths. To look at your failures without flinching. To acknowledge your role in every setback.
Most people won’t pay this price. They choose the comfort of excuses over the pain of ownership. And I get it — ownership hurts. But here’s what they miss:
The pain of ownership is temporary. The cost of avoiding it is permanent.
Every time you choose comfort over ownership, you:
Miss crucial learning opportunities
Weaken your ability to influence outcomes
Train yourself to be helpless
Signal to others that you can’t be counted on
But when you embrace ownership:
Each failure makes you stronger
Your influence grows
You develop antifragility
You attract others who take ownership
This is why I bet on owners: Not because they fail less, but because they turn failures into fuel.
Let me show you why.
The Psychology of Self-Believers: Why Ownership Creates Unstoppable Force
In my quarterly founder meetings (I mentor/advise a few companies), I keep seeing the same pattern play out.
Just last quarter, I met with three founders whose startups were facing critical moments.
Same market conditions. Similar challenges. Radically different responses.
Two of them spent our entire meetings explaining:
Why the market timing was off
How their team wasn’t getting it
What their competitors were doing wrong
When things would magically turn around
They’re still in the same spot weeks later.
The third founder? She walked in with:
Three specific mistakes she’d identified
A clear plan to fix each one
Actions she’d already taken
Early results from changes made
Her company grew 40% last month.
Here’s what’s fascinating: She wasn’t smarter or more experienced than the others. She just had one crucial advantage — she believed she could influence outcomes.
The Science of Self-Agency
When people take ownership, it demonstrates a very powerful perspective shift.
Psychologists call this “locus of control” — the degree to which people believe they have power over their lives. But I’ve noticed something the psychology textbooks miss:
Locus of control isn’t fixed. It’s a muscle. And like any muscle, it grows stronger with use.
Every time you take ownership, you:
Strengthen your belief in your ability to influence outcomes
Increase your capacity to spot opportunities for action
Speed up your recovery time from setbacks
Build resilience against future challenges
It’s a virtuous cycle that compounds over time.
The Ownership Accelerator
Here’s what makes this psychology so powerful: Ownership creates velocity.
Think about two people facing the same problem:
Person A believes external factors are to blame:
Waits for conditions to change
Seeks permission and consensus
Moves cautiously to avoid blame
Reacts to circumstances
Person B owns the situation:
Acts immediately
Makes decisions autonomously
Takes calculated risks
Creates circumstances
By the time Person A is finishing their analysis of why something won’t work, Person B has already tried three solutions and learned from the results.
The Counter-Intuitive Edge
But here’s the part that surprises most people: Owners don’t just recover faster — they actually experience less stress during failures.
Research in performance psychology shows that feeling in control, even during negative situations, significantly reduces stress. It’s not the failure that crushes people — it’s the feeling of helplessness.
This explains why I’ve seen owners remain calm during crises that send non-owners into panic:
They focus on what they can control
They view challenges as temporary
They see failures as data points
They maintain agency even in difficult circumstances
The Ultimate Differentiator
This psychological edge creates a gap that widens over time.
While non-owners are:
Waiting for perfect conditions
Avoiding responsibility
Protecting their ego
Building cases for why things won’t work
Owners are:
Creating opportunities
Taking swift action
Learning from results
Building momentum
This is why I bet on owners: Their psychology creates velocity, and velocity creates results.
The Ultimate Self-Bets: Stories of Radical Ownership in Action
Let me share some examples that prove this isn’t just theory.
We’re talking about real people who bet on themselves when everyone else bet against them.
Sara Blakely: The $5 Billion Self-Bet
Before Spanx became a household name, Sara Blakely was a fax machine saleswoman with $5,000 in savings and an idea for footless pantyhose. What happened next is a masterclass in ownership:
When lawyers told her she couldn’t patent her idea without their expensive help, she bought a textbook and wrote the patent herself
When manufacturers refused to take her seriously, she drove across Georgia visiting plants until she found one willing to try
When retailers wouldn’t give her shelf space, she stocked products herself after hours
When she needed publicity but couldn’t afford PR, she sent samples to Oprah’s makeup artist
She didn’t wait for permission. She didn’t blame the system. She owned every obstacle and found a way around it.
Today, she remains the youngest self-made female billionaire in history.
Howard Schultz: The Coffee Shop That Almost Wasn’t
In 1987, Howard Schultz had to raise $3.8 million to buy Starbucks. After 242 rejections from investors, most people would have blamed the market, their pitch, or their timing.
Schultz’s response? “Every time I was rejected, I refined my pitch. The problem wasn’t the market — it was me. I hadn’t learned to tell the story right yet.”
He kept refining until he got his yes. Then he mortgaged his house to contribute his part of the deal.
That’s ownership. That’s betting on yourself.
Reed Hastings: The $40 Million Mistake
Here’s my favorite ownership story. In 2011, Netflix CEO Reed Hastings made a massive mistake with Qwikster — attempting to split Netflix into two services. The stock plummeted 75%. The internet exploded in outrage.
Hastings’ response?
No blaming market conditions
No pointing fingers at advisors
No hiding behind corporate speak
Instead, he wrote directly to customers: “I messed up. I owe everyone an explanation… It is clear from the feedback over the past two months that many members felt we lacked respect and humility.”
Then he fixed it. Fast.
Most CEOs would have blamed “market conditions” or “customer misunderstanding.” Hastings owned it completely.
Today, Netflix is worth over $100 billion more than before that mistake.
Whitney Wolfe Herd: The Ultimate Comeback
After leaving Tinder amid a sexual harassment lawsuit, Whitney Wolfe Herd could have played the victim. She had every excuse to give up on the dating app industry.
Instead, she took ownership of her future. She built Bumble — a dating app that put women in control. When competitors said the market was saturated, she ignored them. When critics said her approach wouldn’t work, she doubled down.
Result? She became the world’s youngest female self-made billionaire when Bumble went public.
The Pattern You Can’t Ignore
Notice what these stories have in common:
None waited for perfect conditions
None blamed external factors for setbacks
All turned obstacles into opportunities
All maintained ownership of their destiny
But here’s what’s really interesting: Not one of them was the most qualified person to succeed in their field:
Blakely wasn’t a fashion industry insider
Schultz wasn’t from a restaurant background
Hastings wasn’t a media mogul
Wolfe Herd wasn’t a tech veteran
They won because they bet on themselves when no one else would.
The Anti-Pattern: A Warning Tale
Contrast these with Elizabeth Holmes of Theranos. When problems emerged with her blood-testing technology, she:
Blamed engineers for implementation
Accused competitors of sabotage
Claimed media bias
Shifted responsibility to others
The result? The largest fraud case in Silicon Valley history.
The lesson? Success leaves clues. And the biggest clue is how people handle adversity.
The Hidden Signals: How to Spot Self-Believers Before Everyone Else Does
I’ve spent 20 years learning to spot people who bet on themselves.
Here’s my playbook (8 ideas) for identifying them before it becomes obvious to everyone else.
1. Listen to Their Stories
The biggest tell is how people talk about their past.
In any story, listen for these critical differences:
Self-Believers Say:
“I made the wrong call on…”
“I learned that I needed to…”
“I hadn’t yet figured out how to…”
“Next time, I’ll approach it differently by…”
Non-Owners Say:
“The timing wasn’t right for…”
“Nobody told me that…”
“If only they had…”
“You can’t succeed when…”
2. Watch Their First Response to Bad News
The most revealing moment isn’t the failure — it’s the first 5 minutes after bad news hits.
Self-Believers:
Ask “What can I do about this?”
Start problem-solving immediately
Focus on next steps
Look for their role in the outcome
Non-Owners:
Ask “Who’s responsible for this?”
Start defending their position
Focus on explanations
Look for external factors to blame
3. The Meeting Test
Want to spot a self-believer in any meeting?
Watch what they do when things go off track.
Self-Believers:
Raise issues early
Volunteer solutions
Make specific commitments
Follow up without being asked
Non-Owners:
Stay quiet until asked
Point out problems without solutions
Make vague commitments
Wait to be followed up with
4. The Email Signal
Even email patterns tell a story. Look for these markers:
Self-Believer Emails:
“I dropped the ball on this. Here’s my plan to fix it:
1. [Specific action]
2. [Timeline]
3. [Success metric]
Let me know if you need any adjustments to this plan.”
Non-Owner Emails:
“Unfortunately, due to circumstances beyond our control, several challenges have emerged…
We’re hoping that once conditions improve…”
5. The Question Hierarchy
The questions people ask reveal their ownership level.
Listen for this hierarchy:
Level 1 (Lowest Ownership):
“Why does this always happen to me?”
“Who’s going to fix this?”
“When will things get better?”
Level 2 (Medium Ownership):
“What caused this?”
“How can we prevent this?”
“Who needs to be involved?”
Level 3 (High Ownership):
“What can I do right now?”
“How can I prevent this next time?”
“Where did I miss the early warning signs?”
6. The Subtle Red Flags
Watch out for these under-the-radar warning signs:
The Subtle Deflection:
“That wasn’t my understanding…”
“I was told that…”
“Traditionally, we’ve always…”
The Hidden Excuse:
“With everything going on…”
“Given the current situation…”
“Under these circumstances…”
The Responsibility Shuffle:
“I’ll try my best…”
“Hopefully we can…”
“We’ll see what happens…”
7. The Ultimate Test: Give Them Something Broken
Give someone a broken system, process, or project. Then watch:
Self-Believers:
Dive into understanding the problem
Take immediate ownership
Start fixing without being asked
Keep you updated on progress
Non-Owners:
List all the reasons it’s broken
Explain why it’s not their fault
Wait for complete instructions
Update only when asked
8. The Career Pattern
Look at their career trajectory:
Self-Believers:
Have non-linear career paths
Take calculated risks
Choose growth over comfort
Create opportunities
Non-Owners:
Follow traditional paths
Take the safe route
Choose comfort over growth
Wait for opportunities
Now, let me show you why spotting these patterns early is the secret to exponential returns, and how to use this knowledge to make better bets on people…
The Multiplier Effect: Why Backing Self-Believers Creates Compound Returns
Let me share something I’ve never seen fail:
When you bet on someone who bets on themselves, you get more than linear returns.
You get a multiplier effect that compounds over time.
The Mathematics of Self-Belief
Think about what happens when you back someone who takes ownership:
They solve problems faster
Non-owners spend weeks building cases for why something can’t be done
Self-believers spend that same time finding ways to get it done
They learn faster
Non-owners defend their current knowledge
Self-believers constantly update their understanding
They compound faster
Non-owners plateau at their comfort level
Self-believers turn each challenge into a growth opportunity
The Network Effect of Ownership
Here’s where it gets really interesting. Self-believers don’t just perform better — they create upward spirals in entire organizations:
They Attract Other Owners
A senior engineer at Apple once told me: “I joined my team because during my interview, my manager owned up to a massive mistake she’d made. I knew right then this was someone I could learn from.”
They Create Owner Cultures
When Netflix’s Reed Hastings publicly owned his Qwikster mistake, it set a company-wide standard: “We own our failures here.”
They Develop Other Owners
Sara Blakely of Spanx is famous for asking her employees: “What did you fail at this week?” turning ownership of failure into a badge of honor.
Here’s how the returns compound over time:
Year 1: Basic Ownership
Takes responsibility: Stops the blame game and owns outcomes immediately, even the painful ones. When a project misses deadlines, they say “I should have spotted the risks earlier” instead of blaming team bandwidth or external factors.
Solves immediate problems: Jumps into fires without being asked. They don’t wait for permission to fix what’s broken. When they see a customer issue, they handle it immediately rather than waiting for someone else to notice.
Learns from mistakes: Turns every failure into a lesson. Instead of hiding errors, they document them, share them, and build processes to prevent them. They keep a “mistakes journal” and review it monthly.
Year 2: Expanded Ownership
Prevents future problems: Develops an early-warning system for issues. They can spot trouble six months out because they’re looking for it. They’re the first to raise concerns about scalability before it becomes a crisis.
Creates better systems: Builds processes that prevent problems from happening in the first place. Instead of fighting the same fires repeatedly, they install smoke detectors. They automate what can be automated and systematize what can’t.
Develops others: Starts teaching ownership mindset to their team. They mentor junior members, share their thought process openly, and create opportunities for others to step up and own outcomes.
Year 3: Strategic Ownership
Spots opportunities others miss: Sees around corners because they’re not busy making excuses. While others are explaining why something can’t be done, they’re quietly finding the path forward. They spot market shifts early because they’re looking for ways to adapt rather than reasons to stay still.
Builds ownership cultures: Creates environments where ownership is expected and celebrated. They tell stories about ownership wins, reward people who raise problems early, and make it safe to admit and fix mistakes. Their entire team starts operating differently.
Creates exponential value: Compounds everything they touch. Their projects don’t just succeed — they spawn new opportunities. Their teams don’t just perform — they transform. Their influence spreads far beyond their formal authority because others want to replicate their results.
This isn’t just career progression — it’s a complete transformation in how someone operates in the world.
Each year builds on the foundation of the previous one, creating compound returns that most people never achieve because they’re still stuck making excuses in year one.
The Viral Nature of Ownership
But here’s the real magic: Ownership spreads. I’ve watched it happen countless times:
One person starts taking radical ownership
Their results improve dramatically
Others notice and emulate
The behavior becomes contagious
The culture transforms
Let me share one of the best examples of ownership I’ve seen: Brian Chesky at Airbnb’s early days.
In 2008, Airbnb was dying. They had maxed out their credit cards, were $40,000 in debt, and making just $200 a week. Most founders would have blamed the financial crisis, pointed to investor skepticism about their “crazy idea,” or simply given up.
Instead, Chesky took radical ownership of their biggest problem: their listings looked terrible.
Rather than blaming hosts for bad photos or complaining about their lack of resources, he borrowed a camera and personally went door-to-door in New York, taking professional photos of their properties.
He didn’t wait for permission, budget approval, or the “right time.”
He just did it.
The results were immediate: weekly revenue doubled to $400 the first week they replaced amateur photos with his professional ones.
This was ownership in action. No fancy metrics, no committees, no excuses.
Just solving the problem right in front of him.
But here’s where the compound effect kicked in. That simple act of ownership led to:
Discovering that professional photos were key to trust
Creating Airbnb’s professional photography program
Building direct relationships with early hosts
Understanding their market from the ground up
This hands-on ownership mentality shaped Airbnb’s entire culture. Years later, when they faced trust and safety issues, they didn’t outsource the solution — they created a 24/7 customer support line and put founders on rotation for customer service shifts.
Today, when tech CEOs ask me about building ownership culture, I don’t quote statistics or share management theories.
I tell them about Chesky borrowing a camera and going door-to-door. Because that’s what real ownership looks like — solving problems yourself instead of waiting for someone else to solve them.
The company that started with a founder taking photos of apartments is now worth over $50 billion. But more importantly, it started with someone who refused to make excuses and chose to own the solution.
The Exponential Edge
This is the exponential edge at work.
When you back self-believers like Chesky, you’re not just betting on their current capabilities — taking nice photos of apartments.
You’re betting on their capacity to turn small ownership moments into massive outcomes.
You’re betting on their ability to transform “I’ll fix this myself” into “We’ll build a global solution.”
You’re betting on someone who sees every obstacle as an opportunity to build something bigger.
You’re betting on:
Their growth trajectory
Their ability to develop others
Their cultural influence
Their compound learning
Their expanding impact
It’s like investing in a company that:
Doubles its growth rate yearly
Improves its product automatically
Trains its own workforce
Markets itself through results
Compounds its advantages
The Warning Sign
But here’s the flip side — and this is crucial:
When you back non-owners, you don’t just get linear underperformance. You get:
Spreading learned helplessness
Contagious excuse-making
Cultural deterioration
Compound mediocrity
One non-owner in a key position can infect an entire organization with “it’s not my fault” syndrome.
Practical Application: How to Bet on Self-Believers (And Become One Yourself)
Let’s turn all of this into actionable steps.
Here’s my framework for evaluating, developing, and becoming a true self-believer.
The Interview Matrix: How to Spot Owners
When evaluating someone, here are the exact questions I ask:
“Tell me about your biggest failure.” Listen for:
Immediate ownership vs. blame
Specific learnings vs. vague lessons
Action taken vs. philosophizing
Forward focus vs. past justification
“What’s the biggest mistake you’re currently learning from?” Look for:
Comfort with current challenges
Active problem-solving
Specific improvement plans
Real-time ownership
“What’s something you changed your mind about recently?” Watch for:
Willingness to admit being wrong
Evidence of active learning
Comfort with uncertainty
Intellectual honesty
The Development Framework: Building Owners
Want to develop ownership in yourself or others? Here’s my system:
Start Small
Take ownership of one small thing
Build daily ownership habits
Celebrate ownership wins
Learn from micro-failures
Scale Up
Tackle bigger challenges
Own broader outcomes
Lead ownership initiatives
Develop others
Systematize
Create ownership processes
Build feedback loops
Establish ownership metrics
Scale through systems
The Personal Transformation Plan
And if you’re ready to become a true self-believer?
Here’s your 30-day plan:
Week 1: Ownership Audit
Track every excuse you make
Note every blame statement
Record every ownership opportunity
Begin shifting language
Week 2: Response Rewiring
Change “they” to “I”
Replace “but” with “and”
Switch “can’t” to “how can I?”
Transform complaints into requests
Week 3: Action Acceleration
Take immediate ownership of problems
Propose solutions with every critique
Follow up without being asked
Document your ownership wins
Week 4: System Building
Create personal accountability metrics
Build ownership habits
Develop support systems
Share your journey
The Leadership Leverage Points
If you’re leading others, here’s how to create an ownership culture:
Model It
Own your mistakes publicly
Share your learning process
Demonstrate problem-solving
Celebrate others’ ownership
Reward It
Recognize ownership behavior
Promote based on ownership
Share ownership stories
Create ownership incentives
Teach It
Make ownership explicit
Train ownership skills
Mentor emerging owners
Share ownership tools
The Warning Signs in Yourself
Stay alert for these personal ownership slips:
Language Drift
“They should…”
“If only…”
“It’s not fair…”
“Someone needs to…”
Behavior Slides
Waiting for permission
Avoiding tough conversations
Delaying decisions
Making excuses
Mindset Traps
Victim thinking
Entitlement creep
Responsibility deflection
Blame shifting
The Ultimate Ownership Test
Ask yourself daily:
“What am I pretending not to have power over?”
“Where am I waiting for someone else to solve my problem?”
“What excuse am I polishing instead of fixing?”
“Where am I choosing comfort over growth?”
Remember: The goal isn’t perfection. It’s progress. Every time you catch yourself making an excuse, you have an opportunity to choose ownership instead.
The Final Challenge
Here’s your immediate action item:
Identify one situation you’re currently not owning
Write down your usual explanation
Rewrite it from an ownership perspective
Take one action to address it
Repeat
Why This Matters Now More Than Ever
We’re living in extraordinary times:
AI is rewriting the rules of work
Remote work is reshaping opportunities
Economic uncertainty is the new normal
Change is accelerating exponentially
In this environment, there are two types of people:
Those waiting to see what happens to them
Those deciding what happens next
The gap between these two groups isn’t getting smaller. It’s exploding.
What I’ve learned after two decades of watching people succeed and fail:
Talent is common. Ideas are plentiful. Resources are available. But ownership? That’s rare.
And here’s the beautiful thing about ownership: It’s a choice. A choice you can make right now.
You don’t need permission
You don’t need credentials
You don’t need perfect conditions
You just need to decide
Right now, you have a choice:
You can close this newsletter and continue as before
Or you can make today the day you stop:
Waiting for permission
Making excuses
Blaming circumstances
Playing it safe
A Final Thought
Remember those two founders I mentioned at the start?
The excuse-maker’s company closed last week. The owner just raised their Series B.
The future belongs to those who bet on themselves.
The only question is: Are you ready to go all-in on you?
Because I know I’m ready to bet on people who bet on themselves.
Will you be one of them?
— Scott
P.S. If this resonated with you, I have a challenge: Take one thing you’ve been making excuses about. Own it completely. Take action today. Then email me what happened. I read every response.
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Thank you.
This is a wake up call for me, who sometimes manages full accountability, and sometimes fails. I’m learning and I’m loving the ride.