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Pain To Profits: Podcasts For Entrepreneurs
Pain To Profits
223 episodes
1 week ago
Join Samson Jagoras as he rolls up his sleeves and dives deep into the world of buying, building, financing, and investing in small and medium-sized enterprises (SMEs). As a serial entrepreneur and CEO of ClearlyAcquired.com, Samson brings experience in entrepreneurship through acquisition, marketing, branding, and creative strategies.This podcast is your front-row seat to insights and lessons from the trenches of Sleeves Up Equity Building.
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All content for Pain To Profits: Podcasts For Entrepreneurs is the property of Pain To Profits and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Join Samson Jagoras as he rolls up his sleeves and dives deep into the world of buying, building, financing, and investing in small and medium-sized enterprises (SMEs). As a serial entrepreneur and CEO of ClearlyAcquired.com, Samson brings experience in entrepreneurship through acquisition, marketing, branding, and creative strategies.This podcast is your front-row seat to insights and lessons from the trenches of Sleeves Up Equity Building.
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Entrepreneurship
Business
Episodes (20/223)
Pain To Profits: Podcasts For Entrepreneurs
SBA Changes for Business Buyers: What You Need to Know | SOP 50. 10.8 SBA Changes (Effective June 1, 2025)

SBA SOP Changes: What They Mean for Search Funds, Buyers, and the Future of Main Street Acquisitions
An AI-Generated Podcast from the Clearly Acquired Blog Briefing (May 2025)

In this episode, we unpack the major policy shifts in the SBA’s latest Standard Operating Procedures (SOP 50 10 8 and SOP 50 10 7 Clarification), effective June 1, 2025—and explore how they impact search funds, deal structuring, and Main Street business acquisitions.

This AI-generated episode is based on two Clearly Acquired articles: “Major SOP 50 10 8 SBA Changes” and “SBA’s New SOP Clarification”. We dive into the SBA’s intent to modernize and streamline business acquisition lending—while also examining the unintended consequences these changes may have on investor-backed entrepreneurship through acquisition (ETA).

Key Takeaways:

1. Big Wins for Borrowers:

  • Personal Resource Test Eliminated: No longer disqualifies high-earners with liquidity. SBA will now consider “global cash flow,” including spousal income and rental earnings.

  • Seller Notes as Equity: For the first time, seller notes can count toward the 10% equity injection—if placed on full standby for the life of the loan (max 50% of injection).

  • CPA-Prepared Financials: When tax returns aren’t available, lenders can now accept CPA-reviewed statements—ideal for carve-outs, sole props, or new entities.

2. Tougher Rules for Search Funds & Investors:

  • Operator Must Have Control: SBA loans now require the buyer (searcher) to maintain day-to-day control and personally guarantee the loan. Any investor control—even informal or contractual—is prohibited.

  • No Guaranteed Returns: Structures that prioritize investor repayment (e.g., redeemable preferred stock or waterfalls) are now disallowed. Investors must take true equity risk.

  • Co-Borrower Requirements: All owners must sign as co-borrowers; sellers with retained equity under 20% must personally guarantee the loan for at least two years.

3. Structural Shifts and Strategic Tradeoffs:

  • Stock Purchase Mandated in Some Cases: If rollover equity is involved, the SBA will require stock deals—not asset purchases—reshaping tax and liability planning.

  • Self-Funded Searchers Less Affected: Individuals using their own capital to search and raise deal-by-deal remain relatively untouched by these rules—but institutional models will need to adapt.

  • Investor Support at Risk: Critics argue the SBA is misinterpreting the value investors bring (capital, mentorship, strategy), risking more failed deals and fewer exits for sellers.

4. The Bigger Picture:

  • Systemic Misalignment: Rising business valuations aren’t matched by SBA loan limit increases. Fewer deals pencil under the new framework, potentially creating a backlog of unsellable Main Street companies.

  • Need for Nuance: Clearly Acquired advocates for balanced solutions—like milestone-based earnouts or protective provisions that don’t infringe on borrower control.

5. Action Steps for Buyers & Advisors:

  • Rethink deal structure early—especially if relying on investor capital.

  • Ensure all equity is “true equity” with no disguised repayment guarantees.

  • Leverage seller financing creatively within new limits.

  • Build an expert advisory team to navigate compliance and maximize flexibility.

Conclusion:
While SOP 50 10 8 opens the door for more flexible, inclusive SBA-backed acquisitions, the clarified restrictions on investor control present challenges for traditional search funds. These changes could either streamline lending or choke off a generation of entrepreneurial dealmakers—depending on how the market adapts.

This episode was generated using Clearly Acquired’s AI tools and is based on the company’s in-depth 2025 SBA SOP analysis. For the full articles, visit https://www.clearlyacquired.com/blog/major-sop-50-10-8-sba-changes-effective-june-1-2025----what-they-mean-for-business-buyers

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4 months ago
14 minutes 33 seconds

Pain To Profits: Podcasts For Entrepreneurs
From Search to CEO: The Entrepreneurial Acquisition Playbook

The Ultimate Guide to Search Funds: Why Buying a Business Is the New Startup
An AI-Generated Podcast from Clearly Acquired's 2025 Guide to Search Funds

In this episode, we explore The Ultimate Guide to Search Funds (2025 Edition) by Clearly Acquired—a comprehensive briefing on how search funds are redefining the path to entrepreneurship, wealth creation, and legacy building.

Search funds offer a compelling alternative to startups. Instead of building a business from scratch, aspiring entrepreneurs—called “searchers”—raise capital to acquire and operate existing, profitable businesses. These businesses, often valued between $5M and $50M, sit in the “missing middle”: too large for most individuals to buy outright, yet too small for traditional private equity. With baby boomer retirements creating an unprecedented transfer of business ownership, search funds are emerging as a strategic, scalable, and less risky path to ownership.

We trace the evolution of the model—from Stanford MBA roots in the 1980s to today's tech-enabled, globally adopted, and increasingly diverse world of entrepreneurship through acquisition (ETA). The modern searcher is no longer just a freshly minted MBA but also includes mid-career professionals, seasoned operators, and industry experts seeking autonomy, control, and impact.

Clearly Acquired is at the forefront of this movement. Their platform empowers searchers with proprietary deal-sourcing tools, real-time lender data, SBA loan brokerage, investor networks, educational playbooks, and coaching. Whether pursuing off-market opportunities or structuring complex capital stacks, Clearly Acquired supports buyers from first deal to final close—and even invests directly in promising operators through its Catalyst Fund.

We also dive into the mechanics of deal structuring:

  • Traditional vs. self-funded search funds

  • SBA 7(a) and 504 loans, seller notes, and revenue-based financing

  • Creative equity structures and investor expectations

  • Tools to balance risk, ownership, and upside

For corporate professionals, search funds offer a powerful pivot—ownership without startup risk, equity with real upside, and the chance to preserve and grow established businesses that matter to communities. But the transition is not without challenges: mindset shifts, skill gaps, personal risk, and the need to build a solid team of advisors and capital partners.

Finally, we compare search funds to other models like private equity and venture capital, showing how searchers uniquely combine lower risk, strong cash flow, and meaningful operator-led growth.

Key Themes Covered:

  • What search funds are—and why they’re growing fast

  • The evolution from MBA-only to globally accessible ETA

  • How Clearly Acquired supports searchers with capital, coaching, and tech

  • Equity and debt structures that power small business acquisitions

  • Corporate-to-ownership transitions and the skills required

  • The future of ETA and the legacy opportunity

This AI-generated podcast is based on Clearly Acquired’s 2025 Guide to Search Funds—created to help more entrepreneurs and investors understand and act on one of the most powerful trends in modern business ownership.

Whether you’re exploring your first deal, raising capital, or advising others, this episode delivers a clear, actionable snapshot of the search fund ecosystem and how you can participate in the next wave of Main Street entrepreneurship.

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4 months ago
24 minutes 6 seconds

Pain To Profits: Podcasts For Entrepreneurs
Norvell Gives up $4.5M | Mindset of a Navy Seal | Google's Quantum Chip | SBA Loan Updates for Business Buyers
10 months ago
1 hour 12 minutes 31 seconds

Pain To Profits: Podcasts For Entrepreneurs
MSM vs Elon, Juan Soto's a $765M Distraction, Kamala for "Person of The Year?"

In ep. 51, the guys discuss Axios & MSM joining forces vs Elon, why Juan Soto is a $765M distraction, Peter Schiff’s off-take on Bitcoin, Business Storytelling, Scientific Advertising, and a classic commercial from Purple.


00:34 - Axios & MSM Attack Elon Over The Truth

07:51 - Kamala Harris nominated for Person of The Year?

09:06 - Ray Dalio was right about the “Archestypical Big Cycle.”

10:22 - Juan Soto is a $765M distraction

23:03 - The guys ‘welcome’ Peter Schiff to the show

28:58 -  How much equity should you get as an investor?

40:57 - Marc Randolph’s billion-dollar definition of success

44:28 - Dickie Bush breaks down Scientific Advertising

50:04 - Ameen Haque’s 5 Principles of Business Storytelling

56:56 - Purple’s classic commercial is hilarious

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10 months ago
58 minutes 48 seconds

Pain To Profits: Podcasts For Entrepreneurs
Berkshire Hits $300B in Cash, The Digitalization of All Things, and GaryVee is Right About Live Shopping!

In ep. 50, the guys discuss the state of buyer confidence in the market, Berkshire sitting on $300B, the 'digitalization' of all things, and why GaryVee is right about live shopping on social.


0:00 - Episode recap

2:33 - Most Americans have no confidence to buy right now.

3:55 - Berkshire Hathaway’s cash position is now at $300B!

14:03 - Tom Bilyeu explains what focus looks like.

20:39 - Darius explores the thought that we are witnessing the ‘digitalization of all things.’

34:48 - Classic footage from Bezos on why product is greater than marketing.

45:33 - GaryVee explains why live shopping on social is here to stay, but will anybody listen?

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11 months ago
54 minutes 23 seconds

Pain To Profits: Podcasts For Entrepreneurs
Business lessons in College Football, side effects of the YCombinator era, & Jaguar vs Volvo

In ep. 49 of the pod, Darius and Samson discuss entrepreneurship through the lens of college football, the downside of the YCombinator era, Jersey Mike’s $8B sale, and close-out contrasting car makers Jaguar and Volvo.


01:29 - Samson’s entrepreneurial thoughts watching the CU Buffs this weekend

06:18 - Andrew D’Souza on the side effects of the YCominbator era of entrepreneurship

14:14 - Do billionaire operators ever stop feeling broke?

24:36 - Jersey Mike’s selling $8B with ONLY 3,000 locations.

33:31 - Every American owes $106,787…in theory.

34:56 - 700 regional banks are on the verge of failing

40:16 - A word from Trump’s New Treasury Secretary on America’s economic future

43:37 - The guys explore the Jaguar rebrand debacle with help from Newsweek and YouTube creator, Antonio

57:05 - The new Volvo ad makes the guys emotional

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11 months ago
1 hour 5 minutes 30 seconds

Pain To Profits: Podcasts For Entrepreneurs
MBAs Ruin Everything, Elon's Best Move, The Major Exec Sell-Off, & The Trump Shuffle Takes Over

In ep. 48 of the pod, Darius and Samson dig into why you shouldn’t hire MBAs, Elon’s boldest move in business, Rich execs are selling, The Trump Shuffle, and Volvo’s greatest ad ever!


0:00 - Intro

3:51 - Don’t hire MBAs

10:26 - Brian Armstrong on the chaos of startups

17:14 - Codie Sanchez on the power of one idea

20:07 - How Elon made the ultimate chess move

27:11 - Alex Friedman on creating your own reality

29:19 - The commodity basket & inflation are linked!

32:16 - Where is the big money going? Take a look.

37:58 - Steve Blank on The Art of The MVP

43:05 - Greg Isenberg with another must-read post

49:58 - The Trump Shuffle is taking over the country

54:35 - Dickie Bush on Volvo’s greatest ad of all time

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11 months ago
59 minutes 23 seconds

Pain To Profits: Podcasts For Entrepreneurs
Trump Wins, Bitcoin ATH, Naval, Charlie Munger, and Must-See Content For Entrepreneurs

On ep. 47 of the pod, the guys dig into President-elect 47, Bitcoin ATH, The phase of the bull market we are in, Naval, Charlie Munger, how SaaS is evolving, and must-see content and ideas for your business. 

(Thumbnail: Chip Somodevilla/Getty Images)


Episode Breakdown:

00:00 - Intro/Trump’s victory!!

00:50 - When you trust your team but they don’t trust you.

03:02 - Bitcoin resting at an all-time how. Are you in yet?

09:03 - We are in phase 3 of the bull market. Buckle up!

16:55 - Naval, a man on a mission to destroy wokeism.

23:18 - The Charlie Munger operating system for entrepreneurs.

30:52 - Greg Isenberg on the future of SaaS.

37:01 - How Spotify snatched billions of views at no cost.

46:43 - Marketing math that works for the next 10 years.

49:57 - The endless possibilities of creating content on social.

51:13 - Healthy businesses don’t obsess over metrics and goals.

57:08 - The post-election conversation we all need to have.

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11 months ago
1 hour 1 minute 57 seconds

Pain To Profits: Podcasts For Entrepreneurs
25 More Basis Points, 90+ Sam Altman-isms, & Kamala Exploits the Black Church

00:00 - Intro & Check in

02:08 - The Fed cutting rates another 25 basis points

05:45 - Folks are waking up by way of their wallets

09:24 - The Market adjusted for inflation is shocking

18:02 - The US Government debt market collapse has started

25:00 - Interesting social content for entrepreneurs

27:30 - Sam Altman-ism for startup entrepreneurs

38:00 - Marketing wisdom from Rory Sutherland

45:23 - Is the Harris campaign exploiting the "Black Church?"

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12 months ago
52 minutes 27 seconds

Pain To Profits: Podcasts For Entrepreneurs
Keynesian vs Austrian Economics, RIP Multifamily Real Estate, and Must Watch Social Content

Pain Points co-hosts Darius Bell and Samson Jagoras survey the Keynesian vs. Austrian debate, multifamily crumbling, the most accurate recession predictor just went off, and the realities of buying a business from "SMB Attorney." We then jump into social content that surveys marketing and culture.


Episode Rundown:

00:00 - Intro

01:01 - Keynesian vs Austrian Economics survey

19:01 - Multifamily delinquencies are up 990%

22:38 - The Sahm rule has been triggered. Look out!

27:07 - SMB Attorney drops knowledge for folks buying businesses

35:49 - The man who proved time was an illusion

42:41 - Our weekly content and culture showcase

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1 year ago
59 minutes 50 seconds

Pain To Profits: Podcasts For Entrepreneurs
Bank of America in Trouble, 5 Questions to Fix Your Sales, & Building Your 'Personal Brand' in 2025

Pain Points co-hosts Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


00:00 - Intro/Check-in

01:27 - The treasury statement that wasn’t…

05:46 - Porter Stansberry helps us prepare for what’s coming!

12:31 - Is it 07/08 all over again?

23:22 - Business strategy from Jef Bezos

27:37 - How Dan Martell learned scale from Naval

31:47 - 5 questions to completely understand your customer

37:41 - The Deadlift ETF you’re not invested in

42:32 - Chris Do & Dan Koe teach us how to build a brand in 2025

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1 year ago
58 minutes 53 seconds

Pain To Profits: Podcasts For Entrepreneurs
7 Truths of Entrepreneurship, Why Elon Should Inspire You & The Great Content Reset

Pain Points co-hosts Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


02:00 - Another Trump assassination attempt.

10:38 - 7 Truths of Entrepreneurship from Hormozi

26:32 - Economic news, inflation, & evolving Your business

30:00 - Can you remain in the game?

37:45 - Elon Musk should inspire you as an entrepreneur

45:42 - Chris Voss lessons on communication for leaders 

51:28 - How not to run a social cause campaign 

55:17 - A proper ad campaign that won’t cost $10M.

59:13 - Introducing “Rapnamefogie.”

01:07:26 - A closing word on authenticity

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1 year ago
1 hour 8 minutes 26 seconds

Pain To Profits: Podcasts For Entrepreneurs
Raising Cane's Journey to 700 Locations, Concerning Fertility Rates, and Amazon Thief Gets Roasted!

Pain Points co-hosts, Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for entrepreneurs.

0:00 - Intro

02:24 - Raising Cane's founder, Todd Graves, journey to 700 locations!

06:00 - If you’re not pitching, you don’t believe in it

12:35 - New record amount of US debt on the first day!!

17:15 - Marketwatch tries to spin housing news

21:23 - World fertility rates should concern you

27:57 - TrapWavy on the agenda in the black community

31:53 - Kamala gives a lesson on what not to do

35:03 - ReadChoi perfectly gives us the scoop on NC

39:11 - Amazon package gets roasted by victim



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1 year ago
42 minutes 31 seconds

Pain To Profits: Podcasts For Entrepreneurs
Hey Fans, It's Not "Your Team," David Tepper's $21B Strategy, & Andrew Chen On Hitting 100M Users

Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.

🚨Will you do us a solid and consider leaving a review or sharing with someone who you think would dig the podcast!?


Pain Points Episode Rundown:

0:00 - Intro

3:14 - Newsflash: It's Not YOUR Team!

8:18 - PBD's 3 Types of People

16:16 - David Tepper's Billion Dollar Investing Strategy

22:07 - Andrew Chen on Growing to 100M Users

31:35 - The Longshoremen Strike Explain By The AP

41:50 - Our Weekly Content & Ideas Showcase


Join our community, and stay updated on the latest content and news! 🌐 Website: PainToProfits.co 📺 Subscribe: YouTube.com/@paintoprofits 📷 Follow us on Instagram: Instagram.com/PainToProfits 🐦 Connect with us on Twitter: Twitter.com/PainToProfits

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1 year ago
53 minutes 45 seconds

Pain To Profits: Podcasts For Entrepreneurs
Larry Fink Markets Bitcoin, The Looming Recession, & Viral Marketing Lessons From Coors & Colin Landforce

Pain Points co-hosts, Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


Episode Rundown:

0:00 - Intro

2:04 - 60% of the Fed cut rate cycles have led to a recession.

10:20 - Buying conditions have collapsed..what does it mean?

14:00 - US S&P Flash PMI Report

17:00 - BlackRock is preparing with Bitcoin

30:28 - Larry Fink marketing Bitcoin??

33:00 - Iman Gadzhi & Alex Hormozi tell the truth about entrepreneurship

45:10 - The great content showcase

54:30 - Where are the children?

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1 year ago
57 minutes 9 seconds

Pain To Profits: Podcasts For Entrepreneurs
The 2nd Attempt on Trump's Life, The Fed Cuts Are Here, & An M-Top in The Market?

🚨(Warning: Darius' mic was a little hot this episode so adjust your volume accordingly.)🚨

In this episode of Pain Points: Where the World Meets Business, we lead off by touching on the now-second assassination attempt on Former President Trump.

We then jump into the current state of the economy, the latest Fed rate cuts, and what they mean for entrepreneurs. 

Lastly we survey marketing and entrepreneurial insights and close out with a look at the mainstream machine, which is very much a machine at this point.

Timestamps:

00:00 Intro: Setting the stage for the week ahead
03:08 - Political discussion: An assassination attempt on Trump and media survey
07:19 - Breakdown of Trump assassination attempt from the Independent
09:50 - BlackRock’s role in global economics and defense contracts
13:20 - Fed’s interest rate cuts: Will they boost or sink the market?
18:30 - The stock market’s reaction: By the rumor, sell the fact
23:00 - Yield curve inversion: What it signals for the economy
26:00 - Entrepreneurs’ guide: How to prepare and leverage the current market climate
28:00 - Real-world business strategies: Debt, acquisitions, and expansions
31:50 - Matt Gray on Personal Brand Building
38:20 - Sahil Bloom on the 4 types of luck
44:30 - How to make content for personal brand as a beginner
50:00 - An example of the mainstream media machine in action

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1 year ago
53 minutes 23 seconds

Pain To Profits: Podcasts For Entrepreneurs
Codie Sanchez Drops Gem on Wealth, Why College Football Needs CEOs vs Coaches, & Something To Remember Come Election Day

Pain Points co-hosts, Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


0:00 - Intro

3:10 - Codie Sanchez on how to truly get wealthy

12:58 - Why football teams need CEOs instead of coaches

18:20 - Do you know the story of Joe Moglia? You should.

24:30 - A Letter to Future Entrepreneurs

31:00 - What happened to All Birds?

40:23 - The Fed is making its worst policy mistake since 1929.

50:55 - Our weekly content showcase

1:01:50 - Put these on your election-day radar…

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1 year ago
1 hour 10 minutes 28 seconds

Pain To Profits: Podcasts For Entrepreneurs
800k Jobs Disappear, Selling Stories vs Products, & The Real Number Behind Each Candidate

Pain Points co-hosts, Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


0:00 - Intro

2:45 - The Jobs report was off by 800k

7:33 - The RFK Jr Trump endorsement

11:35 - The internet defeats Dave Grohl

13:30 - Stop underestimating Kamala Harris

17:00 - Why the Telegram incident matters

22:14 - Ben Horowitz on new ventures

27:09 - Seth Godin on selling store vs products

29:08 - South Park creators give a storytelling lesson

34:40 - Great content showcase

43:55 - The two candidates head to head with numbers.

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1 year ago
47 minutes 31 seconds

Pain To Profits: Podcasts For Entrepreneurs
Eric Schmidt's AI Predictions, How Nike Beat Reebok At The Olympics, & Why You Need A Brand Evangelist

Pain Points co-hosts, Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


0:00 - Intro

3:03 - The true power of your friends

7:53 - Do something cool and they will come

10:19 - Eric Schmidt on the future of AI & why Google is losing.

24:30 - Why process kills scale 

29:17 - Selling with offense AND defense

31:47 - You need a brand evangelist

34:10 - How Nike got scrappy to beat Reebok

41:10 - Great content showcase

56:40 - The Leprechaun task force

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1 year ago
58 minutes 42 seconds

Pain To Profits: Podcasts For Entrepreneurs
The Market Didn't Crash, airbnb's Startup Saga, & Great Ads You Must See!

Pain Points co-hosts, Darius Bell and Samson Jagoras dive into the ever-changing landscape of entrepreneurship for busy entrepreneurs.


Today's episode breakdown:


0:00 - Intro/Air Drum Jam Session

03:48 - The Fear Index

10:03 - AirBnb’s Cold Start Problem

16:31 - The Ryan Reynolds Playbook

23:19 - Flavor Flav Takes Over Water Polo

28:00 - The Best Day to make Cold Calls

38:00 - The CEO’s Key Responsibilities

32:48 - Great Ads Showcase

38:32 - Communism is Back…Again

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1 year ago
42 minutes 57 seconds

Pain To Profits: Podcasts For Entrepreneurs
Join Samson Jagoras as he rolls up his sleeves and dives deep into the world of buying, building, financing, and investing in small and medium-sized enterprises (SMEs). As a serial entrepreneur and CEO of ClearlyAcquired.com, Samson brings experience in entrepreneurship through acquisition, marketing, branding, and creative strategies.This podcast is your front-row seat to insights and lessons from the trenches of Sleeves Up Equity Building.