BigDeal Podcast Episode #85: Why Playing Small Is Keeping You Broke
Host: Codie Sanchez
Date: August 18, 2025
Episode Overview
In this episode of the BigDeal podcast, Codie Sanchez pulls back the curtain on why playing small in business—especially among women—can keep you financially stuck and unfulfilled. Drawing from her own experience as an investor who sees thousands of business pitches a year, a recent conversation with tech founder Amjad Massan, and candid stories of both failure and success, Codie reveals unfiltered insights on scaling ambition, mastering dealmaking, and the mindset shifts crucial for moving beyond 'lifestyle businesses' to create real wealth and freedom.
Key Discussion Points & Insights
1. Why Women Are Underrepresented as Business Acquirers
[01:15]
-
Women own 40% of businesses, but make up only 2% of buyers in business acquisitions.
-
Codie attributes this discrepancy to both internalized limiting beliefs and societal narratives:
- Many women "tell ourselves really negative stories" about negotiating and deserving more.
- She urges a shift in mindset: "We gotta stop that. We got to start saying that it’s super powerful to be a woman, that actually men are on our side, that we are going to all grow together, that you’re going to make a massive amount of wealth." —Codie [01:45]
-
Women tend to aim for “safe and small” businesses, often due to external conditioning.
- Codie’s challenge: Play bigger. "10x is often easier than 2... If you try to build a really big business, you are going to bumble fuck your way at least into a lifestyle business." [03:37]
2. Thinking Big: Lessons from Amjad Massan (REPLIT)
[03:55]
- Codie recounts a pivotal conversation with Amjad Massan, founder of REPLIT:
- Amjad's ambition: “one billion coders.”
- Amjad's challenge to Codie: “Why are you only trying to create 1 million owners? Why not 100 million?”
— This reframed her perspective on what’s actually possible with scale.
- Takeaway: Have a friend (“a buddy”) who pushes you to think bigger when you’re “playing too small.”
3. Codie’s Business Acquisition Filters
[04:46]
-
Due diligence comes down to two questions:
- Are the numbers real?
- Will those numbers reliably continue?
- "We don’t buy hopes and dreams, we buy realities and cash flow." [04:57]
-
Codie's 'Yes' criteria for buying a business:
- In business for 5+ years (cuts failure risk by over 50%)
- Already profitable, cash flowing day one
- Ability to structure leverage (not all your own money)
- So simple you can "explain it to Grandma"
- Something you’re curious about for at least a few years
-
Her 'No' criteria (Red Flags):
- Businesses with no current profit but “promise” big growth
- Proprietary tech you can’t understand
- Businesses in niches you dislike or lack expertise in
-
Deal Philosophy:
"The best way to do deals is to do what we call a fuck yes deal.”
—Codie [07:24]"Pros obsess on terms. Amateurs obsess on price."
—Codie [09:31]- It's not just about the sticker price; terms (structure, timing, control) will determine a deal’s success.
4. True Stories: The $25 Million Cannabis Catastrophe
[11:01]
-
Codie shares a cautionary tale:
-
Invested $25M into a seemingly thriving cannabis company.
-
Just three weeks later, it was out of cash—due to financial fraud (even the bank and accountants were in on it).
-
Lessons learned:
- Avoid deals where personal relationships are tangled across the team, bank, and accountants.
- Always tranche investments—give money in milestone-based chunks, not all upfront.
- Insist on financial oversight (daily account access, restrictions on large transactions).
-
"Money’s a cruel mistress. She’ll leave you if you don’t pay attention to her." [13:35]
-
“All you want to do is protect your ability to persevere... you can have mosquito bites, that’s OK, but we want to make sure there aren’t great white bites.” [14:35]
-
-
Never fall in love with a deal:
"Don’t fall in love with something that can’t love you back." —Codie’s dad [15:00]
5. Stop Obsessing Over Saving: Earn More Instead
[15:51]
-
Codie argues it’s easier (and more empowering) to focus on earning than penny-pinching:
- "You can only save your way to zero. There is a bottom on it, and you gotta eat and you gotta look cute like you guys all do, and you gotta, like, go out and enjoy life." [15:51]
- Codie shares her own 'broke moments'—from declined cards to banking PTSD.
- Reject toxic scarcity: "Have the fucking coffee. Buy the matcha. That’s not going to stop you from being rich, and it sure as fuck not going to make you rich." [17:31]
-
Focus on dealmaking and financial literacy:
- "Learn about the language of business so deeply that it becomes a fluency... it’s actually not complicated. This stuff is not hard, it’s just not taught." [17:58]
-
Action step:
"Spend 30 days becoming so obsessed with dealmaking and financial literacy and doing business deals that you set up the next 30 years. It’s literally that simple." [18:22]
6. How to Start: Practical Next Steps with $50k
[18:42]
- Start with learning: Get a (good) book on business buying, ideally from the library or secondhand—low risk, high return.
- Reality check: "You can lose money. This is not risk-free... It is not risk free to do financial transactions."
- Go deeper: Take a course, join a community.
- Surround yourself with people whose average is your aspiration: "Are you going to make more money if you’re in a group with a bunch of other people who are obsessed with making money, who already have what you would consider your dream day to be their Tuesday?"
- “Negativity contagious, actual fat contagious… You are more likely to make more money if your friend group has more money. And it doesn't mean we should leave people behind... Bring them with you, but get a couple rich bitches in your group because it helps.” [20:16]
Notable Quotes & Memorable Moments
-
On Playing Small:
“If I was like the big sister who's maybe made a few more bills than you have and has the wrinkles to prove it, I would say this. Women, on average, if we don't play victim mode, we're super, super powerful.” [01:33] -
On Ambition:
“10x is often easier than 2. That actually if you try to build a really big business, you are going to bumble fuck your way at least into a lifestyle business.” [03:37] -
On Deal Terms:
“Pros obsess on terms. Amateurs obsess on price.” [09:31] -
On Risk and the First Deal:
“If your first deal is your worst deal, you'll never do a deal again because it'll scar you and you'll think that deal making is bad, not just that you had stuff to learn.” [11:37] -
On Money:
“Money’s a cruel mistress. She’ll leave you if you don’t pay attention to her.” [13:35] -
On Mindset and Spending:
“You can only save your way to zero... it's much easier to earn than it is to save.” [15:51]
“Have the fucking coffee. Buy the matcha. That’s not going to stop you from being rich...” [17:31] -
On Community:
“Bring them with you, but get a couple rich bitches in your group because it helps.” [20:32]
Important Timestamps
- [01:15] – Why women are underrepresented as business acquirers
- [03:55] – The ‘think bigger’ challenge and story from REPLIT’s Amjad Massan
- [04:46] – Codie’s business dealmaking criteria (the 'fuck yes' deal)
- [11:01] – Disaster story: $25M lost in cannabis investment, and lessons learned
- [14:35] – Protect yourself: “Mosquito bites vs. great white bites”
- [15:51] – Stop focusing on saving; focus on earning, dealmaking, and financial fluency
- [18:42] – Starting steps for buying a business with $50K: Learn, join a community, upgrade your circle
Closing Thoughts
Codie’s message is direct, irreverent, and sharply practical: If you want wealth and freedom, you must stop playing small, challenge your limiting stories, and skill up in dealmaking and financial literacy. The only thing truly keeping you broke is chasing small goals and settling for what feels 'safe'.
Codie’s kicker:
“Get a couple rich bitches in your group because it helps.” [20:32]