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The Prosperisus Pursuits Podcast
Segun Obayendo
23 episodes
6 days ago
Join the host Segun Obayendo for daily 10-15 minute episodes exploring entrepreneurship, brand building, and marketing with purpose. Each week dives deep into a focused topic through five daily segments packed with research insights and actionable strategies. Saturdays feature in-depth case studies with detailed analysis, while Sundays offer personal reflections. Your daily dose of practical wisdom for building a purposeful, profitable business. New episodes daily.
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Entrepreneurship
Business
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All content for The Prosperisus Pursuits Podcast is the property of Segun Obayendo 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 the host Segun Obayendo for daily 10-15 minute episodes exploring entrepreneurship, brand building, and marketing with purpose. Each week dives deep into a focused topic through five daily segments packed with research insights and actionable strategies. Saturdays feature in-depth case studies with detailed analysis, while Sundays offer personal reflections. Your daily dose of practical wisdom for building a purposeful, profitable business. New episodes daily.
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Entrepreneurship
Business
Episodes (20/23)
The Prosperisus Pursuits Podcast
Episode 23 - Building Your Trust System: Complete Integration Framework

Transform this week's trust-building concepts into one complete systematic framework. Execute the 60-minute Master Challenge to create your personal trust system - from authentic story to risk elimination strategy.

You'll finish with what most entrepreneurs never develop: a systematic approach to building authentic relationships that creates competitive advantage. Perfect integration of all week's learning into an immediately actionable business system.

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4 months ago
9 minutes 12 seconds

The Prosperisus Pursuits Podcast
Episode 22 - Warby Parker Case Study

How do you convince people to buy glasses online when everyone said it was impossible? Four MBA students with $120,000 turned the "crazy" idea into a $3 billion company by systematically applying the trust-building principles we've covered this week.

Discover how Dave Gilboa's lost $700 glasses became the origin story for disrupting a monopolized industry. Learn the exact strategies Warby Parker used to hit their first-year sales targets in just 3 weeks and build a 20,000-person waitlist.

This episode shows you the real-world application of Days 1-3: authenticity, competence, and empathy working together to create massive business success. You'll see how trust-building becomes a systematic competitive advantage.

Perfect case study for aspiring entrepreneurs who want proof that authentic business relationships drive real results.

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4 months ago
10 minutes 36 seconds

The Prosperisus Pursuits Podcast
Episode 21 - Demonstrating Competence - Proving You Can Deliver (Without Overselling)

Stop feeling awkward about self-promotion.

Learn systematic frameworks that turn your authentic story into measurable business credibility - no more hoping people will "just trust you."

Discover the SMART Proof-of-Concept Framework, the Trust Stack Builder system, and how to eliminate customer risk like Warby Parker did with their Home Try-On program.

Your 5-minute homework: Pick one simple way to prove you're good at what you do.

Yesterday: Strategic authenticity and vulnerability
Tomorrow: Complete Warby Parker case study - how four broke students built a $3 billion company

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4 months ago
9 minutes 2 seconds

The Prosperisus Pursuits Podcast
Episode 20 - Authenticity in Action - Being Real in a Fake World

How do you be authentically yourself in business without oversharing or seeming unprofessional? Today you'll learn the strategic vulnerability framework that turns your real story into a competitive advantage.

Discover the four levels of vulnerability, why emotions drive 90% of business decisions, and how leaders like Satya Nadella and Brené Brown use authentic storytelling to build trust at scale.

Your 5-minute homework: Write your authentic origin story using the proven framework.

Yesterday: The three pillars of trust
Tomorrow: How to prove you can deliver without overselling

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4 months ago
7 minutes 43 seconds

The Prosperisus Pursuits Podcast
Episode 19 - The Trust Foundation - Understanding the Three Pillars of Trust

Why do some entrepreneurs immediately seem credible while others struggle to prove themselves? Discover the three-pillar framework that separates trusted business leaders from those who can't build relationships.


Learn the Harvard Business Review trust formula, why the trust crisis creates opportunities for authentic entrepreneurs, and which of the three pillars you're probably missing.

Your 5-minute homework: Complete the Trust Audit to identify your focus area.

Perfect for aspiring entrepreneurs ready to build businesses people actually want to buy from.

Part of the "Build Trust Before You Sell" series.

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4 months ago
8 minutes 25 seconds

The Prosperisus Pursuits Podcast
Episode 18 - Putting It All Together: Your Complete Audience Understanding System + Preview: Building Trust

You've done something incredible this week. In this encouraging Week 3 finale, host Segun Obayendo helps aspiring entrepreneurs integrate everything they've learned about understanding their audience, while providing the support and confidence needed to move forward with trust-building.

What You've Accomplished This Week:

• Moved from "I think my customers might be..." to "I know exactly who my people are"

• Developed genuine empathy for the struggles and dreams of those you want to serve

• Learned to speak authentically instead of hiding behind business jargon

• Built a foundation that most established businesses never achieve

What You'll Gain Today:

• Confidence in your new audience understanding skills

• A simple framework that makes everything work together

• Reassurance that you're ready for the next step: building trust

• Support for any overwhelm you might be feeling about implementation

Coming Next Week: "Build Trust Before You Sell" - Gentle, practical strategies for earning trust with the audience you now understand so well.

Perfect for aspiring entrepreneurs who want encouragement, practical guidance, and the confidence to keep building their dream business


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4 months ago
7 minutes 55 seconds

The Prosperisus Pursuits Podcast
Episode 17 - Dollar Shave Club Case Study: How Deep Customer Understanding Built a $1 Billion Brand

Discover how Dollar Shave Club transformed a $4,500 viral video into a $1 billion acquisition by mastering customer understanding. In this detailed case study, host Segun Obayendo breaks down Michael Dubin's exact process for audience identification, emotional profiling, and customer language discovery that disrupted the entire razor industry.

What You'll Learn:

• How Dollar Shave Club identified their real customers (hint: not "men who buy razors")

• The complete emotional journey mapping that revealed customer frustrations

• Before/after examples of customer language vs. industry jargon transformation

• Why "shaving sucks" became more powerful than "precision grooming technology"

• The 5-step framework you can replicate for any business or industry

• Specific audience research methods that cost under $100 to implement

Key Case Study Insights:

• From party conversation to $200M revenue in 4 years

• 48.6% online market share captured from Gillette and Schick

• 12,000 customers acquired in first 48 hours from viral video

• How improv comedy training became a customer research advantage

• Why Unilever paid 5x revenue multiple for audience mastery

Perfect for aspiring entrepreneurs, startup founders, small business owners, and anyone building a purpose-driven business who wants to understand their customers deeply enough to disrupt entire industries.


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4 months ago
10 minutes 11 seconds

The Prosperisus Pursuits Podcast
Episode 16 - Customer Language Discovery: How to Speak Your Audience's Language (Not Yours)

Discover how to find and use your customers' exact language to dramatically improve your marketing results. In this episode of the Prosperisus Podcast, Host Segun Obayendo reveals proven frameworks for customer language discovery that work even if you don't have customers yet.

What You'll Learn:

• Customer language discovery frameworks for aspiring entrepreneurs

• How to research customer language using Reddit, Facebook groups, and online communities

• Psychology of word choice and why changing one word can boost conversions by 30%

• Real case studies: Mailchimp's 30% sales increase from simple language changes

• Free tools and templates for testing customer language before launch

• Common messaging mistakes that kill conversions (and how to avoid them)

Perfect for: Aspiring entrepreneurs, small business owners, startup founders, and anyone building a purpose-driven business who wants to connect authentically with their audience.


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4 months ago
12 minutes 10 seconds

The Prosperisus Pursuits Podcast
Episode 15 - How to Define Your Ideal Customer Emotionally: Beyond Demographics for Entrepreneurs | Prosperisus Podcast

Transform your business by understanding your customer's emotions, not just their demographics. In this episode of the Prosperisus Podcast, discover why companies like Dove (2% beauty study), Old Navy ("Jenny" strategy), and TOMS (profit-sharing evolution) succeed by connecting emotionally with their audience.

Host Segun Obayendo reveals the F.E.E.L. Framework—a proven system for understanding your ideal customer's Fears, Emotions, Expectations, and Language. Learn from Harvard Business Review research showing emotionally connected customers are more than twice as valuable as satisfied customers.

Perfect for aspiring entrepreneurs, teachers considering tutoring, mechanics thinking about consulting, or parents dreaming of starting a business. This episode provides the Customer Empathy Map method, real business examples (no fiction), and practical tools you can implement immediately.

Featured strategies: emotional discovery frameworks, customer language collection, empathy mapping techniques, and the 48-hour emotional discovery challenge. Plus actionable homework to create your complete emotional customer profile.

Stop trying to serve everyone and start understanding someone deeply. Your customer's heart matters more than their wallet


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4 months ago
13 minutes 34 seconds

The Prosperisus Pursuits Podcast
Episode 14 - Your Audience is not everyone

Transform scattered business ideas into laser-focused opportunities. This episode teaches you how to identify your ideal customer using the DEEP framework, validate your audience choice with proven questions, and avoid the "everyone trap" that kills most businesses before they start. Based on research showing segmented campaigns get 202% better results, plus real examples from diverse entrepreneurs. Includes a practical homework challenge to find your perfect audience in 24 hours.


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4 months ago
9 minutes 26 seconds

The Prosperisus Pursuits Podcast
Episode 13 - Week 2 Reflection

Ready to turn your biggest struggles into your biggest business opportunities? This week, we've been building the foundation of your entrepreneurial journey - and today we're reflecting on your transformation.

In this episode, you'll discover:

  • How to identify the ONE problem you're uniquely qualified to solve
  • Why your personal struggles are actually your competitive advantage
  • The difference between problems people complain about vs. problems they pay to solve
  • How to communicate your solution with crystal clarity (confused customers don't buy!)
  • Key insights from Airbnb's success story - solving trust, not just travel

Plus: We're announcing an important schedule change - starting Week 3, we're going Monday-Friday only so you can spend weekends IMPLEMENTING what you learn instead of just consuming content.

If you're tired of sitting in your cubicle dreaming about "someday" starting your own business, this reflection will help you move from dreaming to planning. We'll preview Week 3: "Know Who You're Talking To" - because once you know what problem to solve, you need to get laser-focused on WHO needs your solution.

Perfect for: Corporate employees planning their exit strategy, aspiring entrepreneurs stuck in analysis paralysis, and anyone who wants to build a business that actually matters.

Your struggles weren't obstacles - they were market research in disguise. Time to turn that experience into opportunity.

#Entrepreneurship #StartupAdvice #BusinessStrategy #PersonalBranding #ProblemSolving

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4 months ago
7 minutes 16 seconds

The Prosperisus Pursuits Podcast
Episode 12 - Case study on AirBnB

Airbnb: Solving a Trust Problem, Not Just a Travel One"

How did two broke designers with air mattresses build a $100+ billion company? The answer isn't what you think.

In 2008, Brian Chesky and Joe Gebbia couldn't afford their San Francisco rent. Their solution? Rent out air mattresses to conference attendees. Today, Airbnb has facilitated over 2 billion guest arrivals worldwide.

But here's the real story: They weren't solving a travel problem—they were solving a trust problem.

In this episode, you'll discover:

  • Why most entrepreneurs solve surface problems while winners solve trust barriers
  • The 3-step framework Airbnb used to turn strangers into customers
  • How professional photography increased bookings by 200-300% (and why)
  • The "Trust Equation" that works for any business requiring customer confidence
  • Why Color Labs burned through $41M and failed while Airbnb thrived

Perfect for: Aspiring entrepreneurs, side hustlers, and anyone who wants to understand how to identify and solve problems that actually matter.

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4 months ago
15 minutes 44 seconds

The Prosperisus Pursuits Podcast
Episode 11 - People pay for clarity not confusion

Confused customers don't buy. Period.

In this episode, discover why Color burned through $41 million while Instagram sold for $1 billion - and how the difference came down to one thing: message clarity.

Learn the 10-word rule, three pillars of clear communication, and how to test if your business idea actually makes sense to real people. Plus, get the 3-day clarity sprint that transforms confusing concepts into compelling offers.

Whether you're stuck in a 9-to-5 dreaming of freedom or building your first business, this episode shows you how to communicate so clearly that customers can't help but pay attention.

Your message is your economic lifeline. Make it count.

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4 months ago
11 minutes 33 seconds

The Prosperisus Pursuits Podcast
Episode 10 - Communicating the Problem Clearly to Your Audience

Why do some businesses instantly connect with customers while others get ignored? It's not the solution—it's how clearly they communicate the problem.

Discover why Airbnb's simple "we couldn't afford rent" story built an $80B company, while Color's $41M "revolutionary technology" crashed. Learn the frameworks that make prospects say "How did you read my mind?"

You'll Learn:

  • The PROBLEM Framework for instant recognition
  • Story techniques 7x more memorable than facts
  • How to voice thoughts customers never say out loud
  • The test that predicts if your message converts

Perfect for: Aspiring entrepreneurs and 9-5ers with valuable solutions who struggle to explain why people need them.

Transform your business communication in 10 minutes.

Daily entrepreneurship podcast - New episodes Monday-Sunday

95 words, focused and actionable


Research

RetryClaude can make mistakes.
Please double-check responses.
beta Sonnet 4

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5 months ago
7 minutes 55 seconds

The Prosperisus Pursuits Podcast
Episode 9 - Pick a Problem that pays

Yesterday you identified problems you can solve. Today: which ones will actually pay your bills?

90% of startups fail because they solve problems people complain about but won't pay for. Learn the difference between "nice to solve" vs. "painful enough to pay for" through real failure examples and the frameworks that separate profitable businesses from expensive hobbies.

Your homework: Complete the Commercial Viability Assessment to stress-test your problem against market reality.

Perfect for aspiring entrepreneurs ready to build something that actually works.

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5 months ago
18 minutes 42 seconds

The Prosperisus Pursuits Podcast
Episode 8 - How to identify the problem you are best suited to solve

Feeling stuck between your 9-to-5 and your entrepreneurial dreams? Today's episode reveals why the problems you're best positioned to solve aren't hiding in market research reports – they're sitting in your own experience.

In this episode, you'll discover:

  • The 4 types of problem-solver advantages you already have
  • A proven framework for validating whether your personal struggles are business opportunities
  • Why your biggest challenges might be your greatest competitive edge
  • The 30-day Problem Assessment Sprint that separates real opportunities from wishful thinking

Key frameworks covered:✓ The Expertise-Experience Intersection Method✓ Steve Blank's Customer Discovery Process✓ The Problem-Market Fit Assessment

Perfect for: Aspiring entrepreneurs, 9-5 workers planning their exit, and anyone who's ever wondered "Am I qualified to solve this problem?"

Your homework: Conduct 5 customer discovery conversations in the next 24 hours (we'll show you exactly how)

Tomorrow: "Pick a Problem That Actually Pays" – How to avoid the trap of solving problems that matter to you but don't make business sense.

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5 months ago
17 minutes 9 seconds

The Prosperisus Pursuits Podcast
Episode 7 - Purpose starts with a problem

Discover why successful entrepreneurs don't follow their passion—they solve problems they can't ignore. Learn the difference between passion-driven and problem-driven businesses, plus a framework for identifying problems worth building a business around. Perfect for anyone stuck in the 9-5 cycle dreaming of something more meaningful.


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5 months ago
12 minutes 39 seconds

The Prosperisus Pursuits Podcast
Episode 6 - Week 1 Reflection

Wrapping up our foundational week on "Your Story is Your Brand" - we reflect on the key insights about memorable brands, turning pain into purpose, and crafting authentic origin stories. Plus, we get honest about what might be stopping you from sharing your real story and preview next week's focus: "What Problem Do You Want to Solve?" Your transformation is your qualification to help others transform.


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5 months ago
10 minutes 57 seconds

The Prosperisus Pursuits Podcast
Episode 5 - Case study of Humans of New York

How did an unemployed bond trader build one of the most trusted brands online? This case study reveals the storytelling secrets behind Humans of New York's 15-year success, including the 3-act origin story framework and how Brandon Stanton turned personal struggles into $20+ million raised for others. Learn to build authentic connections through your own story.


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5 months ago
12 minutes 25 seconds

The Prosperisus Pursuits Podcast
Episode 4 - Brand Origin Story

Your Brand's Origin Story | The Prosperisus Podcast

Your story is your most powerful sales tool—but most entrepreneurs tell it all wrong. In today's episode, we break down the 3-Act Origin Story framework that billion-dollar brands use to build trust and drive sales.

What You'll Learn:

  • The neuroscience behind why stories stick (and facts don't)
  • How Sara Blakely, Howard Schultz, and Melanie Perkins transformed pain into purpose
  • The 5 trust-building elements that turn good stories into customer magnets
  • Common storytelling mistakes that kill your credibility
  • A step-by-step framework to craft your one-minute origin story

This Week's Theme: Your Story is Your Brand

Whether you're pitching investors, speaking at events, or just networking, your origin story is what makes people remember you. Stop sounding like everyone else and start telling the story that only you can tell.

Your Homework: Use our 3-Act framework to write and test your origin story with real people this week.

Connect with Segun: Segun@ProsperisusEnterprises.com

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5 months ago
13 minutes 3 seconds

The Prosperisus Pursuits Podcast
Join the host Segun Obayendo for daily 10-15 minute episodes exploring entrepreneurship, brand building, and marketing with purpose. Each week dives deep into a focused topic through five daily segments packed with research insights and actionable strategies. Saturdays feature in-depth case studies with detailed analysis, while Sundays offer personal reflections. Your daily dose of practical wisdom for building a purposeful, profitable business. New episodes daily.