Founder2Founder with Aaron Spivak – Details, episodes & analysis

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Founder2Founder with Aaron Spivak

Founder2Founder Podcast

Business

Education

Frequency: 1 episode/7d. Total Eps: 58

Entrepreneurship isn’t just a career—it’s a relentless, all-consuming way of life.

Welcome to Founder2Founder a raw and unfiltered podcast where host Aaron Spivak pulls back the curtain on what it really takes to build something from the ground up. No sugarcoating, no overnight success stories—just deep, honest conversations with some of the most driven, underrated, and game-changing founders of our time. From brutal setbacks to game-changing mindset shifts, Aaron goes beyond the polished success stories to uncover the unglamorous, deeply personal side of building a business.

As a seasoned entrepreneur himself, Aaron goes beneath the surface and gets into the nitty-gritty of what it truly takes to succeed. He’ll dive into the habits, behaviors, and routines that set elite founders apart, the tactics and strategies that are working today, and the mindset shifts required to push through the hardest moments. Through raw personal stories, late-night struggles, and breakthrough moments, guests open up about what it really means to grow, not just as a founder, but as a person.

Each week, Aaron sits down with visionary entrepreneurs from high-growth startup founders to seasoned CEOs, for real, unfiltered conversations about the highs, lows, and everything in between. Whether you're scaling a company, launching your first venture, or just looking for inspiration, this podcast will give you the insights, motivation, and real-world advice you won’t get just anywhere. If you're ready to strip away the illusion and get real about what it means to build, sacrifice, and thrive, this is the podcast for you. Join us every Wednesday!

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https://www.shopify.com
4600 shares
https://www.prizepicks.com/
1297 shares
https://go.foundersclubofficial.com/intro-fc-aaron
116 shares

https://www.instagram.com/thefoundersclub
81 shares
https://www.instagram.com/spivak
80 shares
https://www.instagram.com/mcuban
42 shares

https://www.linkedin.com/in/aaron-spivak1/
84 shares
https://www.linkedin.com/in/will-nitze/
24 shares
https://www.linkedin.com/in/anne-mahlum/
22 shares

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Score global : 68%

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How Oleg Lee Built a $60M Manufacturing Business From a Family Garage

Episode 36

mercredi 26 novembre 2025 • Duration 53:31

In this episode of Founder2Founder, Aaron Spivak sits down with Oleg Lee, a serial entrepreneur, Guinness World Record holder, father of three, and founder of All About Vibe, a custom pillow company that scaled from a garage operation to generating over $60 million in revenue. Known for turning people’s favorite moments into pillows, Oleg has created products for celebrities like Snoop Dogg, Gary Vee, and Paris Hilton, and partnered with brands like Netflix and Paramount.

Oleg breaks down the raw, behind-the-scenes reality of building a physical product business from scratch, how a Groupon deal triggered massive demand, working with family, and why he eventually stepped back from daily operations. He shares his goal of a $100 million exit, how he handles adversity and why focusing on health, values, and energy has been his ultimate growth strategy. This conversation is a must-listen for any founder scaling a team or navigating the chaos of entrepreneurship.

Chapters:
01:17 – The Dog Pillow That Sparked the Business
02:22 – From Israel to the U.S.: Oleg’s Early Work Ethic
04:05 – The First Custom Pillow: A Tribute to His Dog
05:13 – Building the Business in His Dad’s Garage
07:41 – The Groupon Deal That Created Instant Chaos
08:51 – Fulfilling 20,000 Orders With Family Support
09:59 – From Pre-Made to Fully Custom Designs
11:59 – Transitioning From Wholesale to DTC
12:49 – Working With His Dad: The Challenges and Lessons
14:07 – How Bringing His Wife Into the Business Saved Their Marriage
16:26 – Navigating Family Boundaries in Business
17:13 – Oleg’s Vision for a $100M Exit
19:02 – What He Would Do Differently: No Manufacturing
20:01 – The Problem With Business Advice From Non-Operators
21:30 – Pillows at VCon and Understanding Brand Psychology
23:36 – Creating a Safe and Empowering Culture for Employees
25:15 – Hiring a CEO and Fully Stepping Back
26:28 – Why He Hates Numbers but Still Leads
27:20 – Growing Up in Survival Mode in Beersheba
29:04 – Fixing Machines Himself and Leading by Example
30:22 – What It Took to Build a Self-Sustaining Business
31:37 – The Cost of Listening to the Wrong People
33:13 – Setting a Clear Target for the Exit
36:07 – Aaron’s Story of Selling Hush and Knowing When to Sell
40:34 – Why Oleg Doesn’t Share Product Ideas, He Just Builds
41:31 – Managing Remote Leadership and Scaling From Boca
43:37 – Projected Revenue and the Roadmap to $50M
44:15 – When Summer Outsold Christmas and Production Broke
46:31 – Advice to His 30-Year-Old Self: Prioritize Physical and Mental Health
49:56 – Why Health, Wealth, and Family Are Tattooed Into His Values
51:00 – Surrounding Yourself With the Right Energy

Guest Links:
Website: www.allaboutvibe.com
Instagram: @thatpillowguy

If you're a founder doing $1MM+ in annual revenue, apply for the Founders Club today: https://go.foundersclubofficial.com/intro-fc-aaron

Stay Connected!
Aaron Spivak:
IG: @‌Spivak
Linkedin

The Founders Club
IG: @‌TheFoundersClub
Website www.foundersclubofficial.com

Founder2Founder:
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Building a Company That Runs Without You: Kyle Matthews on Scaling Leadership at Matthews™

Episode 35

mercredi 19 novembre 2025 • Duration 01:10:31

In this episode of Founder2Founder, Aaron Spivak sits down with Kyle Matthews, the Founder and CEO of Matthews™, one of the fastest-growing and now largest privately held commercial real estate brokerages in the U.S. Since launching the firm in 2015, Kyle has scaled the company to nearly 30 offices and over 1,000 employees, closing more than $66 billion in transaction volume. Before his rise in business, Kyle played college football at USC under Pete Carroll, learning firsthand what it meant to be part of a high-performance team, lessons that deeply shaped his leadership style and company culture.

Kyle opens up about the long, uncertain road of early entrepreneurship, including the 17 months he went without earning a single dollar in commission. He shares how the pain of regret from his football days shaped a new personal standard of work ethic and intensity in business. Kyle gets honest about what it really takes to succeed as a founder, the role of a supportive partner, why he front-loaded his life for freedom later, and how he's intentionally designed both business and family life to thrive. This conversation is packed with insights on scaling, sacrifice, and staying grounded.

Chapters:
03:51 – From Football Benchwarmer to Business Beast
05:24 – Lessons From Team Sports That Shaped Leadership
06:45 – The Regret That Still Fuels Kyle Today
08:32 – Building a Career With No Plan B
10:02 – How Waking Up at 4:45 Became a Competitive Advantage
12:41 – 14-Hour Workdays for 10 Years Straight
14:21 – 17 Months Without a Paycheck and Why He Didn't Quit
18:33 – When Hard Work Didn’t Translate to Results, Yet
20:15 – How Early Struggles Made His Boss's Job Harder
21:10 – The Real Impact of Marrying Young
24:48 – The Secret to Aligned Relationships While Scaling
27:01 – Would He Be as Successful Without His Wife?
31:41 – Designing His Life to Be Fully Present for His Kids
33:17 – How NFL Players Actually Spend Their Time
34:45 – His Dad's Role Model Blueprint for Fatherhood
36:59 – Coaching His Son’s Football Team While Running a Company
38:30 – Why Your 20s Shouldn’t Be Spent “Enjoying Life”
40:00 – The Myth of Work-Life Balance
42:02 – How Matthews™ Scaled From 15 People to 1,000+
45:23 – Why Kyle Left a Public Company to Start His Own
46:45 – The Business Model That Made Matthews™ Explode
52:47 – Scaling as a CEO: From Founder to Strategic Leader
54:36 – The Intuition Trap: When Founders Need to Let Go
59:08 – What Kyle Would Tell His 33-Year-Old Self
1:03:29 – Buying Matthews.com From a Basement-Dwelling Domain Squatter
1:06:13 – Why You Must Choose Your Hard in Life

Links:
https://www.matthews.com
IG: @kylematthewsceo
LinkedIn: Kyle Matthews
YouTube: Kyle Matthews
Podcast:

Founder2Founder:
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From 0 to 2,000+ Person Events: Lucy Nelles on Community, Profit, and Scale

Episode 26

mercredi 10 septembre 2025 • Duration 59:34

In this episode of Founder2Founder Aaron Spivak sits down with Lucy Nelles, leading community-building expert and co-founder of Coffee & Chill Miami, the wildly popular bi-weekly sober wellness party that now draws over 1,000 guests per event. With over 100 sold-out events and collaborations with top global brands, Lucy has cracked the code on making in-person gatherings profitable, scalable, and deeply impactful.

She shares how she went from feeling isolated in a new city to building a movement, and now teaches others to do the same through her program, Community Mastery. Listen in for insights on team structure, brand partnerships, pricing strategy, and how to build meaningful connections without alcohol.

Chapters:
02:14 – Introducing Lucy: From Isolation to Community
03:46 – The Move to Miami & Early Challenges
04:34 – The First Event That Sparked It All
05:10 – Ice Baths, Stock Tanks & the Rise of a Trend
06:59 – How Coffee & Chill Was Born
08:03 – Losing $10K on One Event (and What She Learned)
09:30 – The #1 Mistake Event Hosts Make
11:00 – The First Coffee & Chill: JBL Speakers & 250 Guests
12:38 – Gradually Raising Ticket Prices & Building Trust
13:57 – Driving Repeat Attendance Every Two Weeks
16:24 – Special Collaborations: Art Basel, F1, NFL
17:18 – How Lucy and Her Co-Founder Divide and Conquer
19:39 – Keeping a Healthy Co-Founder Relationship
21:06 – Investing in Learning for Herself and Her Team
24:28 – Launching Community Mastery to Serve Others
26:09 – Balancing Two Businesses Without Burnout
27:37 – Time-Blocking, Non-Negotiables, and Systems
30:26 – Expanding Coffee & Chill Into New Cities
31:45 – How to Stand Out in a “Saturated” Market
33:31 – Rethinking Nightlife: No Booze, All Wellness
38:54 – Why Lucy Quit Drinking and What Changed
43:07 – Overcoming Imposter Syndrome Through Results
45:45 – The Bigger Mission: Building In-Person Culture

Guest Links:
Website: https://coffeeandchill.com/
Instagram: @luceilanelles & @coffeeandchillmiami

Kintsugi: The AI-powered tax compliance platform trusted by over 3,000 companies worldwide

Founder2Founder:
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Youtube @‌Founder2Founder.Podcast

From a $900 Bank Account to a $50M Brand: Chris Meade on Building CROSSNET

Episode 25

mercredi 3 septembre 2025 • Duration 01:11:16

In this episode of Founder2Founder, Aaron Spivak sits down with Chris Mead, co-founder of CROSSNET and Founders Club, for his most open and personal conversation to date. From a small Connecticut town, to building one of the fastest-growing backyard sports brands in America, Chris unpacks the highs, lows, and lessons of scaling a startup from scratch.

They dive into the origins of CROSSNET, the $1M mistake during an acquisition, the toll of leadership decisions, and how those experiences shaped the vision for Founders Club. If you’re navigating the founder journey, this episode is packed with the kind of honest insights you won’t get anywhere else.

Chapters:
02:49 – Growing Up in Small-Town Connecticut
04:40 – From Film School, to HBO, to Burnout
06:30 – Learning Amazon Dropshipping in College
08:26 – Fired, Broke, and Starting Over at Uber
12:49 – Inventing CROSSNET in a Backyard
15:06 – Quitting Jobs and Moving to Miami
17:49 – Going All-In with Marketing
19:21 – $87K to $9.8M: CROSSNET’s Hockey Stick Growth
21:30 – The Year Everything Went Wrong
25:19 – The Mistake of Not Cutting Fast Enough
28:10 – Trusting the Wrong CFO and Losing Sight
30:01 – The Acquisition That Fell Apart
33:50 – Picking the Wrong Buyer for the Wrong Reasons
35:10 – The Second Exit: Why Vivier Was the Right Fit
38:15 – What He’d Tell His Younger Self
42:04 – Why He Wouldn’t Change a Thing
42:46 – Building Founders Club from Scratch
46:41 – What Makes the Community Work
49:29 – There’s No Real Community for Founders… Until Now
51:07 – What a Great Member Looks Like
54:10 – Building a Life Beyond the Business
57:15 – Relationships Compound Like Capital
58:19 – Founders Forum and the Future of Events
1:00:51 – The Long-Term Vision for Founders Club
1:06:49 – Why This Will Never Be a Suit-and-Tie Club

Guest Links:
Instagram: @crossnetgame & @chrismeade
Website: https://vivereltd.com/pages/crossnet

Kintsugi: The AI-powered tax compliance platform trusted by over 3,000 companies worldwide

Founder2Founder:
TikTok @‌Founder2FounderPodcast
Youtube @‌Founder2Founder.Podcast

The 3 Traits Every High-Growth Brand Shares, According to Shopify’s President Harley Finkelstein

Episode 24

mercredi 27 août 2025 • Duration 58:13

In this special episode of Founder2Founder, Aaron Spivak sits down with Harley Finkelstein, President of Shopify, for a no-fluff, behind-the-scenes conversation recorded live with over 100 Founders Club members. Harley unpacks the deep connection between personal identity and building lasting companies, while discussing how founders can grow smarter and why success demands unshakable character and long-term thinking.

This isn’t a surface-level chat, Harley dives into the psychological drivers behind great founders, how AI is changing hiring and operations, and why you should fire yourself before it’s too late. He shares tactical insights on platform strategy, what Shopify looks for in celebrity-led brands, and how to build a company that’s authentic, resilient, and scalable. From DJing at 13, to leading one of the most iconic tech companies globally, Harley’s founder journey is packed with clarity and conviction that every entrepreneur can learn from.

Chapters:
01:28 – Balancing Personal Brand vs. Business Brand
06:49 – Why Founders Must Go Direct (and Skip Legacy Media)
07:27 – 3 Traits of the Most Successful Brands
12:45 – How AI is Replacing Full-Time Roles at Shopify
14:20 – Growing Firebelly Tea with Fewer People and More Energy
15:47 – Hire Founders, Not Résumés
17:44 – Why Shopify is Run by Founders (and How That Works)
19:06 – Harley’s Grandfather & Building with Character
23:49 – Work-Life Integration & Founders in Relationships
28:11 – Daily Habits, Self-Awareness & Why Harley Meditates
31:29 – The Only Meetings Harley Never Misses
34:38 – When Shopify Builds In-House vs. Letting Apps Thrive
40:35 – What Business Are You Really In? Harley Coaches a Founder Live
46:12 – How to Stop Losing DTC Sales to Amazon
50:01 – Why It Doesn’t Matter Where the Sale Happens
50:44 – Shopify’s Celebrity Strategy (It’s Not About Fame)
55:50 – Harley’s Final Ask: Help a Founder IPO

Guest Links:
Instagram: @Harley & @Shopify
Website: https://www.shopify.com

Founder2Founder:
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From $2,500 in Debt, to the World's Finest Tea Brand: Steve Schwartz on Building Art of Tea

Episode 23

mercredi 20 août 2025 • Duration 01:19:30

In this episode of Founder2Founder, Aaron Spivak sits down with Steve Schwartz, Master Tea Blender, best-selling author, and founder of Art of Tea—an award-winning tea brand based in Los Angeles. After dropping out of college to care for his mother, Steve discovered Ayurvedic medicine and began a journey that would take him across the globe sourcing and blending the world’s finest teas.

Starting with $2,500 in credit card debt, Steve built a vertically integrated company that now supplies iconic restaurants and hotels. He shares how he turned tragedy into purpose, created the U.S.’s first tea sommelier role, and built a legacy-focused business with intention and heart.

Chapters:
02:32 – Losing His Mother and the Awakening of Purpose
04:11 – Discovering Ayurveda and the Art of Botanical Blending
06:23 – The Truth About Supermarket Tea
07:12 – The Power of Ritual: Why Tea Is Not Just a Beverage
08:52 – Choosing Steady Growth Over the Hockey Stick
11:03 – Building with a Multi-Generational Vision
12:35 – American Flips vs. Eastern Longevity Thinking
14:40 – Why Art of Tea Avoids Supermarkets
16:03 – Creating the First Tea Sommelier Position in the U.S.
17:22 – Expanding Art of Tea to the East Coast
19:13 – Controlling Quality Through Vertical Integration
21:16 – Coaching vs. Babysitting: Leadership Lessons
22:12 – The Daily Work of Unlearning Scarcity
25:37 – Childhood Scarcity and the Roots of Limiting Beliefs
28:08 – From Rabbi Aspirations to Global Tea Advocate
30:00 – Smiling as Strategy
33:14 – The Power of Giving Before You Receive
36:44 – Parenting, Abundance, and Entrepreneurial Mindsets
39:58 – Why Entrepreneurship Is the Best Way to Live
43:30 – Creating Safe Spaces for Founders to Be Real
45:29 – Betting on Himself With a Baby on the Way
47:09 – Filling an Org Chart by Removing Himself
50:11 – DJ Fails and the Power of Vulnerability
53:01 – The Real Reason People Join Founder’s Club
54:06 – Building Grit in the Next Generation
55:46 – One Day a Week Off: Shabbat as a Business Advantage
57:12 – What His Late Mother Would Say Now
59:14 – A Message to His 20-Year-Old Self
1:00:33 – The Power of Trust Over Fear
1:03:19 – What He Wants to Be Remembered For
1:05:53 – Getting Out of Your Own Way
1:07:20 – What’s Actually Going On With Matcha
1:11:39 – Matcha Sourcing Crisis and the Japan Trip That Changed It
1:13:55 – The Matcha Trend Explained
1:18:06 – Closing Reflections on Legacy and Leadership

Guest Links:
Website: https://www.artoftea.com/
Instagram: @artofteala @steveschwarx
LinkedIn: Art Of Tea Steve Schwartz

FERMÀT: The AI nat

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From $10 in the Bank to a $9M Beverage Brand: Megan Klein’s Unconventional Path with Little Saints

Episode 22

mercredi 13 août 2025 • Duration 01:26:19

In this episode of Founder2Founder, Aaron Spivak sits down with Megan Klein, founder of Little Saints, the sugar-free, mushroom-powered non-alcoholic cocktails and spirits brand redefining the way we drink. A former environmental attorney turned two-time brand founder, Megan’s journey is one of radical pivots, personal reinvention, and unshakable self-belief. She shares how she went from shutting down her first startup to investing her last million, selling her own apartment to fund it, and scaling Little Saints to $9.6M in revenue without traditional VC backing.

Megan opens up about her lowest moments, from navigating loneliness during the pandemic, to hitting $10 in her personal bank account, and the turning point that came from trusting her own intuition over outside “expert” advice. She dives into how plant medicine shaped her leadership style, the hard lessons of Shark Tank, and why aligning brand growth with personal growth has been the foundation of her success. This is an unfiltered conversation on grit, discernment, and building a category-defining CPG brand on your own terms.

Chapters:
02:21 – From Lawyer to Rooftop Farming
04:51 – The Fog of Misalignment in Corporate Life
07:41 – Equity-Only Hustle at Farmed Here
08:22 – Building The Fresh Factory from a Failed Startup
11:42 – Fundraising Lessons from the First Business
12:35 – Investing Her Own $1M to Start Little Saints
14:37 – The Solo Founder Reality During the Pandemic
16:42 – Hemp Silk Cocktail Masks: The First Little Saints Product
18:05 – The Dry January Experiment That Sparked the Brand
21:00 – Discovering Ayahuasca and Plant Medicine’s Impact
28:55 – Quitting Alcohol for Good
32:39 – Going All-In with DTC
36:09 – Selling Assets to Save the Business
39:50 – Crisis Summer: Cancellation, Family Emergency, and Cash Shortage
41:06 – Unlearning the Need for Outside Approval
46:57 – Filming Shark Tank and Walking Away from the Deal
51:01 – Scaling from $100K to $9.6M in Three Years
53:17 – Laying the Foundation for $20M+ Growth
56:53 – Using Plant Medicine to Become a Better Leader
59:08 – Radical Feedback from the Team
1:03:26 – Little Saints Dirty Martini Demo
1:07:20 – Building in Miami and Creating the Little Saints House
1:11:32 – In-Person vs. Remote Team Dynamics
1:13:08 – What December 2020 Megan Would Be Most Proud Of
1:16:03 – Message to a 16-Year-Old Megan
1:18:39 – Blending Personal Development with Business Growth
1:21:31 – Choosing Alignment Over Short-Term Gains
1:22:23 – Where to Buy Little Saints

Guest Links:
Website: littlesaints.com
Instagram: @littlesaintsco
LinkedIn: Little Saints

Fully Accountable: Mention this ad and have your onboarding fees waived at https://fullyaccountable.com

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The Future Will Be Built by Founders Who Understand AI—Mark Cuban on How to Stay Ahead

Episode 21

mercredi 6 août 2025 • Duration 58:33

In this special episode of Founder2Founder, Aaron Spivak brings you an unfiltered masterclass with legendary entrepreneur and investor, Mark Cuban. Recorded live for members of The Founders Club, this exclusive session covers Cuban's raw insights on building billion-dollar companies, the unglamorous truths of scaling, and how AI is rewriting the rules for modern founders. From sleeping on floors to exiting for $5.7 billion, Cuban reflects on his journey and the mindsets that separate the winners from everyone else.

Mark doesn’t hold back; he dives into why founders should stop glamorizing fundraising, how sales always win over hype, and the one habit that will leave your competition behind. He shares honest perspectives on balancing relationships and business, the brutal reality of hiring the wrong CEO, and how to futureproof your company in the age of AI. Whether you’re bootstrapping or scaling fast, this episode is packed with tactical clarity and real founder-to-founder advice.

Chapters:
01:40 – Why Personal Brands Are Overrated
03:15 – The One Trait All Successful Founders Share
05:45 – Sales First, Always
07:40 – Raising Capital Is Not an Accomplishment
09:34 – Work-Life Balance? Wait Until You're Winning
12:20 – How AI Is Changing the Game (and Why You Can’t Delegate It)
15:00 – How Founders Should Be Learning AI Right Now
17:15 – When to Sell (Even If You're Loving the Business)
20:00 – Why College Accreditation Is Fundamentally Broken
22:00 – What’s Next for Higher Education in an AI World
24:00 – Why You Should Think Twice Before Publishing Anything
25:55 – Should You Hold Back Expansion When Prepping for Exit?
27:40 – Launching Into Sports Partnerships the Smart Way
29:45 – Niche Product? Why You Should Be More Expensive
32:10 – When It’s Time to Hire an External CEO
34:30 – How Mark Leverages ChatGPT in Real Business Decisions
36:20 – Fundraising in a Tough Market: Take the Money or Bridge?
39:00 – Handling Tariffs and Scaling Beyond Local Markets
41:00 – One Simple Daily Habit That Pays Big Mental Returns
44:55 – Should You Expand Your Product Line or Focus Deeper?
47:15 – Promoting Internally vs Hiring for Scale
49:45 – Equity Strategy: What’s Too Much, What’s Too Little
52:30 – The Belief Cuban Had to Unlearn About Leadership
54:50 – "Don’t Be a-”: A Founding Principle That Pays
55:45 – What Every Founder Needs to Learn About Healthcare Costs
57:15 – Mark’s Final Word: Keep Showing Up

Guest Links:
Instagram: @mcuban
TikTok: @mcuban

Fully Accountable: Mention this ad and have your onboarding fees waived at https://fullyaccountable.com

FERMÀT: The AI native commerce platform that optimizes shopping experiences, leading to best-in-class shopper engagement and conversion. FermatCommerce.

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Larysa Nakonecznyj: She Walked Away From Law School, Then Built a Top Global Agency

Episode 20

mercredi 30 juillet 2025 • Duration 01:07:44

In this episode of Founder2Founder, Aaron Spivak sits down with Larysa Nakonecznyj, CEO of Nako Creative, an award-winning digital marketing agency known for driving measurable results through innovation and tailored strategy. With a background in communications and advertising, Larysa has helped global brands grow fast and grow smart. She’s been recognized with the 2024 Global Recognition Award and was nominated for the Women Empowerment Foundation’s “Rising Star” award.

Larysa unpacks the exact moment her path shifted after a single shift waiting tables, and how she walked away from law school to build something of her own. She shares the story behind her first pitch, scaling too fast, bouncing back from burnout, and the mindset work that’s kept her going. This conversation is a powerful look at what it takes to build a solo agency to seven figures while staying grounded in vision and values.

Chapters:
01:40 – Realizing She Wasn’t Meant to Work for Anyone
03:23 – First Corporate Job & Red Flags
04:59 – The Shift at The Keg That Changed Everything
06:12 – Pitching an Agency She Hadn’t Built Yet
07:33 – The Woman Who Believed in Her First
08:33 – Faking a Florida Trip to Buy Time
09:38 – Where Her Standard for Excellence Comes From
11:29 – Walking Away From Law School
12:57 – Breaking the News to a Traditional Family
14:10 – Seeing Opportunity Everywhere
15:59 – Manifesting Confidence Before the Pod
17:44 – Prepping for the Next Hour, Always
19:15 – Discovering “The Secret” and Shifting Mindset
22:54 – When Scaling Too Fast Breaks the System
24:46 – Burnout and Questioning It All
26:14 – Almost Going Back to School
28:14 – Saying No Becomes the New Strategy
30:01 – Doing It Alone Without a Co-Founder
32:08 – From Doubting to Betting on Herself
33:47 – Building Confidence Through Results
35:29 – Curating a Circle That Believes In You
37:54 – Two Types of Friends (Choose Wisely)
39:17 – Life After Exit and the Power of Community
41:54 – The Mental Weight of Being a Young CEO
44:54 – “Move With Confidence”, The One Conversation That Shifted Everything
46:54 – Building Systems Through Mistakes
48:08 – Why Most Agencies Don’t Work Hard Enough
50:18 – The Ferrari x Art Basel Win
52:59 – The Internal Team Mentality Clients Love
55:20 – Advice to Her 20-Year-Old Self
56:13 – Designing a Business Around the Life She Wants
59:35 – Naivety Can Be a Superpower
1:01:09 – The Truth About Building a Business
1:04:31 – Retention as the Ultimate KPI
1:05:32 – Final Word: Show Up, Work Hard, Win!

Guest Links:
Website: https://nakocreative.com/
Instagram: @nako.creative
LinkedIn

Fully Accountable: Mention this ad and have your onboarding fees waived at https://fullyaccountable.com

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Two Exits Before 20: What Austin Copeland Knows About Building, Leading & Letting Go

Episode 19

mercredi 23 juillet 2025 • Duration 01:08:18

In this episode of Founder2Founder, Aaron Spivak is joined by Austin Copeland—a 21-year-old founder who’s already built and sold two companies, including COMPREADY, acquired by CosmicWire. From founding a nonprofit at 13 that delivered over 13,000 shoes to kids in Africa, to managing a 25-person team at global esports giant TSM, Austin’s journey is driven by one mission: improving people’s lives.

He unpacks how he went from gaming enthusiast to building an analytics model that led to six-figure player buyouts, what it takes to stay true to yourself in high-pressure environments, and why being surrounded by the right people can accelerate everything. Now overseeing COMPREADY under CosmicWire, Austin is focused on optimizing computer performance at scale—all while continuing to grow into the entrepreneur he was built to be.

Chapters:

02:24 – A Childhood Immersed in Business
03:40 – First Taste of Entrepreneurship: Beachside Hustles
04:51 – Flipping Burgers at 13: Real-World Lessons
06:03 – Rejecting the “Right Path” and Going His Own Way
07:51 – Selling His First Business at 19
08:03 – Gaming as Passion and Profit
09:29 – Building a Data-Driven Talent Engine
11:30 – COVID’s Influence and Seizing Opportunity
13:28 – The First Exit: Acquired at 16
14:17 – Earning $80K and Managing 25 People
15:43 – The Spark Behind COMPREADY
17:19 – Leaving a Safe Role to Build Again
18:46 – Sacrifice and Identity in the Startup Grind
20:22 – Going All In at 18
22:35 – Choosing College Amid Success
24:37 – The Moment He Knew It Was Real
25:50 – Exit #2: COMPREADY Acquired by CosmicWire
27:03 – Leadership Mistakes and Learning the Hard Way
28:40 – Not Everyone Has Your Fire
30:13 – Making Decisions Through Noise
31:27 – Becoming Unapologetically Himself
33:46 – Vision for 30 and Long-Term Fulfillment
35:45 – The Mentors Who Changed the Game
38:41 – “It’s OK”: How Reassurance Moves Founders Forward
42:44 – Experience Over Theory, Every Time
45:50 – Giving First and Building Reputation
47:11 – Manifesting the Jet and What It Represents
50:59 – Freedom, Frustration, and Fuel
52:04 – You’re Only Out When You’re Dead
54:25 – Don’t Judge What You Haven’t Tried
56:39 – Volunteering to Learn and Grow
58:22 – Advice to His 15-Year-Old Self
1:03:29 – Life in Reverse: Start From the End
1:04:49 – Your Environment Won’t Always Grow With You
1:06:28 – The Power of Being Good Energy