Forward Obsessed

Betting On Blockchain: The Future Of Sports Betting With Alex Dubin

Alex Dubin is the Founder and CEO of BettorOff, a sports betting platform designed to bring transparency and integrity to bettors through blockchain technology. After a few early career twists and turns, Alex Dubin leveraged a chance meeting in a poker game to pivot into sports betting just as daily fantasy sports (DFS) was taking off. He helped set up an investment fund that delivered over 70% returns by deploying algorithms and analytics to beat platforms like DraftKings and FanDuel. However, regulatory changes aimed at these DFS market leaders ultimately crushed Alex’s fund after an impressive 23 month run. Showing perseverance, he co-founded a sports data and analytics company focused on the exploding esports industry and was acquired within two years.
 
Alex then combined his passion for sports and his legal background to co-found BettorOff. With over 50 million sports bettors in the U.S. relying on questionable information sources, BettorOff verifies betting records and gives handicappers an equitable way to build reputation and community. The company wants to be the go-to source for sportsbook players and content creators in a niche Alex calls the “OnlyFans for sports betting”. He believes relentless pursuit of purpose and passion is key to thriving through the startup wilderness.
 
Episode Outline
(00:00:00) Introduction
(00:01:29) Early career and background
(00:04:48) College struggles and resilience
(00:07:01) Getting Miami Heat internship
(00:10:00) Learning from Coach Pat Riley
(00:14:44) Launching fantasy sports fund
(00:18:26) Leaving law firm
(00:22:45) Shutting down the fund
(00:24:37) Pivoting to sports data startup
(00:26:34) ESPN partnership
(00:30:56) Acquisition by SportsGrid
(00:35:27) Starting BettorOff
(00:41:03) Building remote teams
(00:44:31) Fundraising approach
(00:48:19) Previous startup exits
(00:50:07) Parent reactions
(00:52:15) Vision for BettorOff
(00:55:52) Handicapper transparency
(01:00:07) Sports betting portfolio model
(01:02:18) Social network aspects
(01:06:57) Remote work culture
(01:17:53) Monetization models
(01:20:10) Market viability
 
Episode Links
BettorOff: https://www.bettoroff.com/Miami Heat: https://www.nba.com/heat
Alex’s LinkedIn: https://www.linkedin.com/in/alex-dubin-41834261/
Pat RIley Wikipedia: https://en.wikipedia.org/wiki/Pat_Riley
Winning Time (TV SHow): https://en.wikipedia.org/wiki/Winning_Time:_The_Rise_of_the_Lakers_Dynasty
Support & ConnectForward Obsessed Website: www.forwardobsessed.comInstagram: https://www.instagram.com/forwardobsessed/
TikTok: https://www.tiktok.com/@forwardobsessedLinkedIn: https://www.linkedin.com/showcase/forward-obsessed/

Breaking Barriers For Women In Tech With Beverly Parenti

Beverly Parenti is an entrepreneur, philanthropist, and cofounder of The Last Mile, a nonprofit providing technology training to incarcerated individuals. She has founded and cofounded several other successful companies, including First Virtual Holdings, one of the first online payment systems, which went public in the 1990s.
 
In the interview, Parenti stresses the importance of grit, resilience, choosing the right partners, and providing second chances. She recounts the origins of her entrepreneurial spirit from her parents, both survivors of the holocaust, along with the incredible story of her father escaping the Nazis. She discusses cofounding First Virtual Holdings and other startups, as well as cofounding the KickLabs accelerator, which successfully launched massive companies like Wish.com. Her current project is The Last Mile, which provides training in coding, web development, and other technical skills to prepare incarcerated individuals for careers in technology upon release. The organization has expanded to 8 states and gained support from leaders in business, government, and philanthropy. Parenti emphasizes the need to break generational cycles of incarceration and allow individuals to become productive members of society. Her journey and the work of The Last Mile showcase the power of purposeful work, compassion, and redemption.
 
Episode Outline
(00:00:00) Introduction of Beverly Parenti
(00:02:10) Parenti's childhood and entrepreneurial parents
(00:08:53) Launching the First Virtual Holdings payment system
(00:14:01) Moving to California and starting retail businesses
(00:21:34) Getting into tech/consulting in San Francisco
(00:25:57) Meeting Chris Redlitz and joining his startup
(00:30:34) Taking First Virtual Holdings public
(00:31:03) Leaving First Virtual Holdings and consulting
(00:33:48) Joining AdAuction.com with Chris Redlitz
(00:44:27) Starting KickLabs Accelerator
(00:51:02) KickLabs success stories like Wish.com
(00:55:50) Partnership with Chris Redlitz
(01:05:59) Cofounding The Last Mile nonprofit
(01:11:39) Expanding The Last Mile to reduce recidivism
 
Episode Links
 
Marketplace Consulting: https://www.marketplaceconsultinggroup.com/
The Last Mile: https://thelastmile.org/
The Last Mile Radio: https://thelastmileradio.org/
HBR Case Study on First Virtual Holdings: https://store.hbr.org/product/first-virtual-holdings-inc-a/98E007#:~:text=Source%3A%20Ivey%20Publishing-,First%20Virtual%20Holdings%2C%20Inc.,and%20services%20over%20the%20Internet.
 
Support & ConnectForward Obsessed Website: www.forwardobsessed.comInstagram: https://www.instagram.com/forwardobsessed/
TikTok: https://www.tiktok.com/@forwardobsessedLinkedIn: https://www.linkedin.com/showcase/forward-obsessed/

Best Of Forward Obsessed - 2023 Holiday Recap

This year, we had 25 incredible interviews. 25 deep dives into the rollercoaster experience of building a company -  taking an aha moment, nurturing it into a tangible idea for a business, building a team, getting funding, growing, failing, pivoting, growing again, failing again, exploding, and then - who knows. Every story is different - and yet, our team has been able to tease out some of the throughlines from all of these stories, the fundamental truths of entrepreneurship. We are taking everything we are learning, and we are creating a book - the ultimate field guide to building a business. Next Year, we will be taking the first 50 episodes of forward Obsessed and will distill this priceless entrepreneurial knowledge into a single book, one that we plan to get into your hands by next summer. Stay tuned :) 
Being Forward Obsessed means taking your learnings from the past and applying them to the endeavors of the future with unbending resolve, curiosity, and ambition. One thing we have learned is that we have the best fanbase ever - thanks to people like you, sharing our episodes and clips, we reached over 3 million people in 2024 across all our channels. 
As our year draws to a close, We are doing our yearly wrap, and we need your help, the audience, the listeners, who we do it for, to find the best clip. We have decided to award 5 of you a free Forward Obsessed T-shirt, one of the legendary “Progress, Pitfalls, and Pivots” mugs you see on every episode, and a signed copy of the Forward Obsessed book when it drops next year. In order to be eligible, you have to do the following: Pick out your favorite Forward Obsessed clip from our social media, share it to your instagram, share it to your instagram TikTok, share it to your instagram LinkedIn account, and Tag us so we can see it, and you will be in the running
From the entire team here at Digital Surgeons in New Haven Connecticut, we would like to thank you, the viewers and listeners, for your support, your feedback, your energy, and your genuine excitement that you shared with us in the last year. As a part of our end-of-year tradition, we decided to compile the top moment from every episode in the last year, as chosen by our viewers and listeners through their engagement. Like last year, It was tough to omit any piece of knowledge that our amazing guests brought to the table, as every episode presents a brilliant perspective on what it means to be an entrepreneur. I hope you enjoy these clips, take inspiration from these outstanding minds, and step into the new year refreshed and Forward Obsessed. 
Support & Connect
 
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/
 

From Startup To Selling For Half A Billion With Ben Kartzman

Ben Kartzman is the COO of Mediaocean, a multi-billion dollar ad tech company. He was previously the CEO and co-founder of SpongeCell, an ad tech startup that was acquired by FlashTalking. Kartzman has successfully navigated multiple acquisitions and integrations throughout his career in ad tech.
In this interview, Kartzman outlines his journey from college soccer player to serial entrepreneur. He shares stories and lessons learned from the rise and fall of several startups, including gritting through the dot-com crash and having to lay off employees during the 2008 financial crisis. Kartzman stresses the importance of autonomy, transparency, building the right team, and learning to balance optimism with realism as an entrepreneur. He also provides an inside look at acquisition negotiations and building rapport with potential buyers. For entrepreneurs and aspiring founders, this interview offers hard-won wisdom on persevering through difficult times, pivoting business models, and creating successful exits. Kartzman shows that with resilience, adaptability, and the right teammates, one can navigate the turbulent waters of the startup world to build substantial companies.
Episode Outline
(00:00:00) Introduction of Guest: Ben Kartzman(00:04:43) Kartzman's Early Interest in Entrepreneurship(00:10:13) Kartzman's Experience During the Dot-Com Bubble(00:14:28) Pivoting to Consulting(00:18:18) Learning Entrepreneurial Skills Through Consulting(00:20:09) Key Lessons from Early Mentors(00:23:33) Working at a Startup While Having a Full-Time Job(00:27:03) Kartzman's Strong Work Ethic and Drive(00:29:03) Modeling Entrepreneurship and Work Ethic for His Kids(00:35:31) Founding SpongeCell and Early Pivots(00:39:04) Focusing on Revenue Instead of Fundraising(00:41:19) Making Difficult Decisions Like Layoffs(00:43:52) SpongeCell's Innovations in Ad Tech(00:45:26) The Dangers of Prematurely Scaling(00:49:55) Navigating Shifts in Market Dynamics(00:52:17) Thoughts on Middle Management(00:53:01) Acquisition Offers and Deciding to Remain Independent(01:00:39) Navigating Conflicts with Investors(01:04:40) Choosing the Right Acquirer(01:08:23) Traits to Look for in a Buyer(01:10:35) Was the FlashTalking Acquisition Serendipitous?(01:12:38) Joining FlashTalking Post-Acquisition(01:18:49) The Importance of Retaining Your Team Through Exits(01:19:33) Being COO of a Multi-Billion Dollar Company(01:21:49) Does Kartzman Miss Being a Startup CEO?(01:25:13) The State of Ad Tech Innovation Today
Episode Links
Mediaocean: https://www.mediaocean.com/
FlashTalking: https://www.flashtalking.com/
SpongeCell: https://www.spongecell.com/
Toga Builders: http://www.togabuilders.com/
Carnegie Mellon University: https://www.cmu.edu/
Seabridge: https://www.seabridgegold.com/
BridgeLine: https://www.bridgeline.com/
Accenture: https://www.accenture.com/
Union Square Ventures: https://www.usv.com/
Dissidia/Guidestar: https://www.guidestar.org/
Support & Connect
Digital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/
 

From The Bronx To A 9-Figure Exit With André Swanston

Andre Swanston is the former CEO and Co-Founder of Tru Optik, a data and analytics company focused on connected TV (CTV) and streaming media. Tru Optik was acquired by TransUnion for over $100 million when Andre was under 40 years old.
Andre has an incredible backstory, growing up in the Bronx as the son of immigrants from St. Kitts and Nevis. He attended a prestigious boarding school on scholarship, which opened up opportunities but also required tremendous personal sacrifice and perseverance. After dabbling in restaurants, nightlife promotion and financial services, Andre had the vision to create TruOptik when he saw streaming media was going to transform the industry.
Despite the many systemic obstacles facing Black founders in fundraising and scaling startups, Andre managed to bootstrap early operations and eventually raise VC funding for Tru Optik. He built an exceptionally diverse leadership team that out-hustled the competition. Tru Optik focused on dominating the nascent connected TV space years before it became the center of digital media. Their technology and exclusive partnerships enabled them to accelerate rapidly when streaming demand exploded during the pandemic.
Now Andre has set his ambitious sights on bringing an MLS soccer team to Connecticut by 2026. He sees huge untapped potential in making it one of the most valuable soccer clubs globally, with the state's dense population, high income, passion for sports, and strategic location in the Northeast market. His bold goals, perseverance in the face of obstacles, and commitment to his team make Andre a standout founder story.
Episode Outline
(00:02:00) Andre's immigrant upbringing and early drive for education(00:05:38) Getting a scholarship to a prep school and grinding with independence(00:10:00) Dealing with stereotypes and recognizing common motivations(00:13:32) The evolution of his family's status over generations(00:15:37) Attempts at entrepreneurship with restaurants and nightlife promotions(00:21:28) Witnessing friends and clients pursuing startup investments(00:23:42) Recognizing streaming media as the future and assembling a founding team(00:28:41) His wife becoming a crucial partner in the business(00:32:04) Strategically building an exceptionally diverse team(00:34:01) Dominating the market by focusing early on connected TV(00:37:04) The systemic funding obstacles facing Black founders(00:39:30) Locking in partnerships and IPs years in advance of the streaming boom(00:42:16) Structuring an acquisition deal to reward the team's sacrifice(00:44:00) Weighing future fundraising potential vs securing a strategic win(00:46:47) Bold visions setting the stage for going after an MLS team(00:51:46) Assessing the untapped market potential in Connecticut
 
Episode Links
Andre’s LinkedIn ( https://www.linkedin.com/in/andreswanston/)
Andre’s Website (https://www.swanston.org/)
Andre’s Twitter (https://twitter.com/AndreSwanston)
TruOptik, Acquired by TransUnion) (https://www.transunion.com/)
 
Support & Connect
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/

Working Hard Is Not Enough With Jared James

Jared James is an entrepreneur, investor, speaker, and author who was previously the #1 ranked realtor in the country. He has built numerous successful companies across industries like real estate, marketing, technology, and business coaching, and is an accomplished public speaker. 
 
In this wide-ranging conversation, Jared shares insights from his journey starting with formative childhood experiences that ignited his entrepreneurial drive from a young age. He talks about the mindset shifts that propelled his success, including learning to run a business rather than just working hard, focusing on avoiding failure rather than chasing validation, and leveraging skills like public speaking and relationship-building. Jared provides tactical advice for entrepreneurs looking to build visibility and connect directly with their audience. He stresses the power of social media, email marketing, and speaking engagements to reach potential customers. A key mindset shift he recommends is creating content with no expectation of immediate returns.
The interview covers topics like authentic self-expression, managing success, and navigating criticism. He also shares how he stays grounded through constant self-reflection.
 
Episode Outline
(00:00:00) Introduction to Jared James
(00:02:00) Jared's childhood and entrepreneurial beginnings
(00:07:15) Jared's experience working odd jobs and realizing he wanted more
(00:10:00) Jared getting into real estate and becoming number one agent in the country
(00:15:00) The difference between working hard and working smart
(00:20:00) Jared's uncle advising him to aim higher in life
(00:25:00) Jared transitioning into public speaking and building his personal brand
(00:30:00) Being your authentic self publicly vs. privately
(00:35:00) Responding to jokes/comments that offend some people
(00:40:00) The duality and insecurities within successful people
(00:45:00) Jared building direct relationships with his audience
(00:50:00) Jared's journey with writing books
(00:55:00) The role of feedback and criticism in becoming successful
(01:00:00) Jared being introverted and letting few people see his full personality
(01:05:00) Drawing boundaries on how much of yourself to share publicly
(01:10:00) Jared's portfolio of companies and entrepreneurial pursuits
(01:15:00) The real estate industry and reactions to lawsuits
(01:20:00) Jared's First Up real estate tech company
(01:25:00) Jared acquiring companies to solve problems he sees
(01:30:00) Jared leveraging everything in his life to do more with less
(01:35:00) Rejecting the fear of rejection and putting yourself out there
(01:40:00) Where to find Jared online
Episode Links
Connect with Jared: https://www.connectwithjared.com/
Website: https://www.jaredjamestoday.com/
Enjoy Success Today (Book): https://www.amazon.com/ENJOY-SUCCESS-TODAY-Thriving-Business/dp/160145855X
Get Out of Your Way (Book): https://www.amazon.com/Get-Out-YOUR-Jared-James/dp/1633672786
Podcast Info
Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql
Support & Connect
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/

The Future Of Pain Management With Arun Nijhawan

Arun Nijhawan is the co-founder and CEO of Menda Health, a startup using therapy to provide drug and surgery-free treatment for chronic pain. He was previously co-founder of FillMyFork, a startup focused on healthy eating that was acquired by FoodSmart. Nijhawan studied astrophysics in college before moving to Silicon Valley to participate in the prestigious Alchemist accelerator program run by billionaire VC Tim Draper. He overcame significant health challenges starting from a young age, including lifelong kidney disease that required a transplant at age 18 and years of debilitating chronic back pain. 
In this wide-ranging interview, Nijhawan shares his origin story as the son of immigrant entrepreneurs and discusses the difficulties facing children of immigrants navigating between cultures. Nijhawan also talks about developing chronic back pain while working at FoodSmart, which led him on a journey of research and discovery into new ways of treating chronic pain focused on the brain and nervous system rather than just the physical structure.
The interview provides an inside look at Nijhawan's latest venture Menda Health, which takes a similar approach to treating chronic pain by training therapists and using technology to increase access. He explains how they pivoted to a tech-enabled services model and now accept insurance to remove barriers for patients. Nijhawan argues passionately that the current healthcare system is failing people with chronic pain, costing $650 billion annually, and needs to change its focus from surgeries and medications to nervous system-based treatments. For young entrepreneurs, he shares lessons on bootstrapping and patience in startup journeys.
OUTLINE:
(00:02:00) Growing up as son of immigrant entrepreneurs(00:05:00) Navigating Indian and American cultures(00:07:15) Overcoming health challenges from a young age(00:10:00) Developing chronic back pain while working at startup(00:12:30) Embarking on research into new chronic pain treatments(00:17:00) Having a pivotal moment realizing pain pathways changing(00:20:00) Founding chronic pain treatment startup Menda Health(00:25:00) Pivoting from app to tech-enabled services model(00:30:00) Raising first funding round for Menda Health(00:35:00) Being acquired by FoodSmart with first startup(00:40:00) Moving from hustle culture to slower, patient approach(00:45:00) Explaining how chronic pain is often brain-created(00:50:00) Detailing the high cost of ineffective chronic pain treatment(00:55:00) Achieving pain freedom with nervous system-based care(01:00:00) Providing Chronic Pain treatment through virtual therapy(01:05:00) Building infrastructure to scale impact(01:10:00) Fostering human connection to address root of pain(01:15:00) Envisioning paradigm shift in how pain is addressed
EPISODE LINKS:
Arun’s LinkedIn: https://www.linkedin.com/in/arunnijhawan/
Arun’s Instagram: https://www.instagram.com/nijhawhat
Menda Health: https://www.menda.health/
PODCAST INFO:
Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql
 
SUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/
 

Resilience, Love, And Never Giving Up With Alan Lazowski

Alan Lazowski is the founder and CEO of LAZ Parking, the largest privately held parking company in the United States. Alan has grown LAZ Parking from being a valet parking attendant to running over 3,600 locations and 1.5 million parking spaces across 41 states. The company manages over $2 billion in annual revenue. 
The interview focuses heavily on stories from Alan's family background. Alan's parents are both Holocaust survivors from Poland; Alan’s father was only 11 years old when the Nazis invaded his village. Through an incredible story of perseverance, Alan’s father survived the ordeal and came to America to build a new life with his wife, a survivor from the same village in Poland. 
Alan credits his persistence and "never give up" attitude to his family's story of surviving against all odds. The stories from Alan's childhood underpin the culture and values at LAZ Parking today, such as leading with love, believing in second chances, and valuing employees as family.
Overall, this interview provides a fascinating origin story of a successful parking empire, from Alan's humble beginnings to running one of the largest companies of it’s kind in the United States. More importantly, it offers inspiration, wisdom, and values that any entrepreneur or leader should learn from. Alan's perseverance and philosophy is a model to follow.
 
OUTLINE:
(00:00:00) Intro(00:01:30) Alan's origin story and family background as Holocaust survivor(00:07:00) Surviving the Nazi ghetto and selection that saved Alan's father's life(00:10:00) Father's journey as refugee to America and becoming a rabbi(00:13:00) Starting the valet parking business in college(00:18:00) Expanding into parking garage management(00:19:00) Surviving real estate crash and $8M debt(00:23:00) Building company culture and leading with love(00:26:00) Giving second chances (Will Cordero story)(00:29:00) Being generous and the "yes" mentality(00:31:00) Supporting other entrepreneurs(00:35:00) Surviving the COVID pandemic(00:40:00) Developing resilience(00:44:00) Continuous learning and education(00:49:00) Hopes for a movie about his family's story(00:53:00) Focus on people's passion, not just profits(00:57:00) Unlocking potential and talent in employees(01:00:00) Pivoting during COVID with new ideas and innovations
 
 
EPISODE LINKS:
LAZ Parking: https://www.lazparking.com/
Conscious Capitalism: https://www.consciouscapitalism.org/
Faith and Destiny (book by Alan's father): https://www.amazon.com/Faith-Destiny-Philip-Lazowski/dp/0977959619
Into the Forest (book about Alan's mother by Rebecca Frankel): https://www.amazon.com/Into-Forest-Holocaust-Survival-Triumph/dp/1250267641
PODCAST INFO:
Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql
 
 
SUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/

Surviving The River And Building The Bridge With Wiley Cerilli

Wiley Cerilli is a serial entrepreneur and founder of companies like Seamless Web, SinglePlatform, and Good Uncle. He was previously the VP and General Manager of Constant Contact after they acquired his company SinglePlatform for $100 million. Throughout his career, Cerilli has experienced immense personal and professional growth, including overcoming the tragic loss of his father at a young age.
The interview covers Cerilli's inspirational journey, from losing his father while in high school and becoming "CEO" of his family, to the lessons he learned from successful exits at Seamless Web and SinglePlatform. He provides tactical advice for entrepreneurs on topics like fundraising, hiring, sales, product development, and maintaining work-life balance through difficult times. Cerilli stresses the importance of community and resilience when dealing with trauma and chaos. He shares vulnerable stories and actionable frameworks like "Test, Tune, Scale" that provide invaluable insights for young founders. This emotional yet practical interview exemplifies how entrepreneurs can draw strength from hardship, build empathy and vision, and manifest success through perseverance.
OUTLINE:
(00:00:00) Intro
(00:00:31) Introduction to Wiley Cerilli's background and entrepreneurial journey
(00:02:39) Losing his father to cancer at a young age and the impact on his family
(00:05:50) Overcoming adversity and tragedy through entrepreneurship
(00:07:15) Getting his start in startups at Seamless Web
(00:10:00) Starting Single Platform and lessons on fundraising
(00:14:02) Founding ghost kitchen startup Good Uncle
(00:17:02) Entrepreneurial mindset and creating urgency
(00:22:39) Exiting Single Platform to Constant Contact
(00:28:27) Research on childhood loss and achievement
(00:31:36) Starting the non-profit Experience Camps
(00:35:18) Balancing urgency and breaking people in business
(00:43:22) Being ahead of the market with Good Uncle
(00:52:14) Building sales teams and call centers
(01:00:38) Emotions after a big exit
(01:06:14) Grieving as an entrepreneur
(01:10:00) Skipping steps when scaling companies
(01:15:11) Selling Good Uncle to Aramark
(01:17:02) Founding House Account and digitizing home services
 
EPISODE LINKS:
Wiley’s LinkedIn: https://www.linkedin.com/in/wileycerilli/
Wiley’s Twitter: https://twitter.com/wileycerilli?lang=en
Seamless Web: https://www.seamless.com/
SinglePlatform: https://my2.singleplatform.com
Good Uncle: https://www.gooduncle.com/
Experience Camps: https://experiencecamps.org/
David and Goliath Book: https://www.amazon.com/David-Goliath-Underdogs-Misfits-Battling/dp/0316204374
Thinking Fast and Slow Book: https://www.amazon.com/Thinking-Fast-and-Slow-audiobook/dp/B005Z9GAJG
The Perfect Storm Movie: https://www.imdb.com/title/tt0177971/
PODCAST INFO:
Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql
 
SUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/

How To End Prison Recidivism With Chris Redlitz

Chris Redlitz is the Co-Founder and Executive Director of The Last Mile, leading a national movement across our country to provide in-prison technology education and post-incarceration mentorship to justice-involved people across the United States. Chris had previously sold a chain of running stores called Second Sole, founded and sold AdAuction.Com, co-founded Kicklabs, and co-founded Transmedia Capital, a fund and incubator that has helped launch and grow 38 tech companies to massive exits.
After spending his young-adult years on adventures around the world, including a 3-person sailing trip to Hawaii with no digital navigation equipment, Chris followed his passion for ultra-running and founded Second Sole, a retail store in California for high-level running equipment. Chris’ leadership in that space caught the attention of the rapidly growing sportswear giant Reebok, and Chris' meteoric rise in Reebok and his instrumental role in its massive IPO was the first of many profound successes in his life. Sensing the impending dot-com boom, Chris ventured into the digital realm at the perfect moment, leading to multiple successful acquisitions. 
Throughout the interview, Chris shares personal stories and anecdotes that shed light on the realities of entrepreneurship. From the pain of a failed IPO to the importance of having a supportive partner, Chris' stories captivate and inspire listeners. Chris' experience and wisdom offer valuable lessons and insights for navigating the challenges and opportunities that come with building a business.
OUTLINE:
(00:00) Intro
(2:00) Early years as a rebel
(6:40) Dropping out college to sail to Hawaii 
(13:00) Where my rebellious spirit came from
(16:30) Becoming addicted to running and opening a running store
(19:00) Joining Reebok as they grew from $10M to $4B
(21:41) Why Nike succeeded where Reebok failed
(24:04) Transitioning into the Dot Com Boom with AdAuction.com 
(27:00) What the Dot Com Boom was like
(30:00) The mental benefits of running
(37:00) Recovering from the Dot Com crash
(41:30) Starting a VC company that actually cares about their founders
(52:00) Know which moonshot idea to invest into
(56:15) Why are VC funds going dry? 
(1:03:25) Why Safenotes killed the VC industry
(1:09:53) The Last Mile - Technology training in prison
(1:13:49) Entrepreneurship in prison
(1:18:00) Building a movement across political lines
(1:20:30) Why previously incarcerated people are the hardest workers
(1:24:40) Building a company by and for incarcerated people
 
EPISODE LINKS:
The Last Mile: https://thelastmile.org/
The Last Mile WIkipedia Page: https://en.wikipedia.org/wiki/The_Last_Mile_(prison_rehabilitation_program)
Twitter: https://twitter.com/TLM
LinkedIn Page: https://www.linkedin.com/company/the-last-mile/
Youtube: https://www.youtube.com/channel/UCxnslwxnp3acFh13V-uvvJQ
Chris’ Twitter: https://twitter.com/chrisredlitz
Chris’ LinkedIn: https://www.linkedin.com/in/chrisredlitz/
Chris’ Instagram: https://www.instagram.com/credlitz/
PODCAST INFO:
Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql
 
SUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/