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As we approach the summer, the Forward Obsessed podcast is taking a brief but much needed break from creating new entrepreneurial content for you, our incredible listeners. We're grateful for the remarkable guests who have made season three a success, and we have some amazing stuff coming down the pipeline. During this hiatus, we invite you to stay engaged with us: visit our YouTube channel, subscribe, leave comments, and share your favorite episodes. Your feedback is invaluable and helps us shape future content - Don't forget to visit www.forwardobsessed.com to share your favorite moments and suggestions for future guests. We're committed to exploring all facets of entrepreneurship, and your support keeps us in this podcasting game.
We also have an important announcement: this is the final episode with our executive producer, Robert Roche. Since day one, Robert has been instrumental in every facet of the production process, from finding guests, to the full production of the episode, clips, and articles, all the way through answering your questions and comments on our social channels. We wish him all the best in his future endeavors and hope to collaborate again in the future. Robert, thank you for your dedication, creativity, and passion. Your presence will be greatly missed.
From Robert: Please stay in touch! If you ever have a question about podcasting or content management, find Robert P. Roche III on Linkedin.
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Sam Parr, the founder of The Hustle and the host of the My First Million podcast, shares his entrepreneurial journey from his humble beginnings in St. Louis, Missouri, to building and selling successful companies. Parr's early hustles, including selling whiskey online and running a hot dog stand, laid the foundation for his future endeavors. Despite a setback with Airbnb, Parr persevered and started a roommate matching business, which he eventually sold to Apartment List.
Parr's success with The Hustle, growing the company's newsletter to over 1.5 million subscribers, is a testament to his skills in hiring passionate people and his ability to "brute force" a company to success. He offers valuable insights on the emotional challenges of selling a company and the importance of focus and perseverance in building a successful business.
This episode is a must-listen for aspiring entrepreneurs, founders, MBA students, and managers, as it provides practical advice and inspiration from someone who has successfully navigated the ups and downs of the startup world. Parr's candid discussion of his experiences, from cold calling to angel investing and growing a podcast, offers a wealth of knowledge for those looking to build and scale their own ventures.
Episode Outline
(00:00:00) Introduction of Sam Parr
(00:01:28) Sam Parr's background and early entrepreneurial ventures
(00:10:00) Building and selling a roommate matching company
(00:14:02) Starting The Hustle and growing the newsletter
(00:22:36) Hiring strategies and building a strong company culture
(00:29:00) The emotional journey of selling The Hustle to HubSpot
(00:35:00) Life after the acquisition and starting a new company, Hampton
(00:40:45) Branding, positioning, and pricing strategies
(00:44:49) The art of the cold call and its importance in business
(00:50:00) Angel investing experiences and lessons learned
(00:55:00) Building a community with Hampton and differentiating from competitors
(01:02:04) The power of personal branding and visibility
(01:07:31) Hiring and working with CEOs
(01:13:57) The impact of fatherhood on entrepreneurship and personal growth
(01:17:31) Strategies for growing a successful podcast
Episode Links
The Hustle (company): https://thehustle.co/My First Million (podcast): https://www.mfmpod.com/Hampton (company): https://joinhampton.com/Sam's List (website) - https://samslist.co/The Game (book) - https://www.amazon.com/Game-Penetrating-Secret-Society-Artists/dp/0060554738Glengarry Glen Ross (movie): https://en.wikipedia.org/wiki/Glengarry_Glen_Ross_(film)
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/
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Saknas det avsnitt?
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Ben Lamson is the Head Of Revenue at Paperspace, a GPU cloud and software stack for machine learning and artificial intelligence developers, which was recently acquired by Digital Ocean. Previously, he was the co-founder and CEO of WeDidIt, a crowdfunding platform for nonprofits that was acquired by a private equity firm. Lamson's entrepreneurial journey began in his early twenties, inspired by his parents, who were both successful small business owners despite not having college degrees. Growing up in a close-knit family in Kalamazoo, Michigan, Lamson learned the value of hard work and determination from a young age. In college, Lamson pursued his passion for wrestling, becoming a Division I athlete at American University.
Lamson's career in sales began at Meltwater Group, where he met his future co-founder, Sisu Suh. Together, they left Meltwater to start WeDidIt, hacking their way through the startup process by entering business plan competitions, winning grants, and participating in accelerator programs. Through their scrappy efforts, they raised a total of $3.5 million for WeDidIt before successfully exiting to a private equity firm. After the acquisition, Lamson joined Paperspace as the Revenue Leader, where he implemented a product-led growth strategy that resulted in a 350% revenue increase in just 12 months. His success caught the attention of Digital Ocean, who acquired Paperspace in 2023.
Throughout the interview, Lamson shares valuable insights and advice for aspiring entrepreneurs, such as the importance of being curious, asking the right questions, and constantly learning. He emphasizes the value of resilience and grit, drawing parallels between the challenges of wrestling and the struggles of building a startup. Lamson also discusses the future of generative AI and its potential impact on various industries. This episode is a must-listen for anyone interested in entrepreneurship, sales, product-led growth, and the future of AI. Lamson's inspiring journey from college wrestler to successful startup founder and revenue leader is a testament to the power of hard work, determination, and continuous learning.
Episode Outline
(00:00:00) Introduction
(00:07:49) Discovery of wrestling passion and its impact
(00:17:21) Service industry experience and lessons learned
(00:21:58) Starting a tech company with a co-founder from Meltwater
(00:26:29) Idea evolution and the aha moment for WeDidIt
(00:28:46) Hacking the startup journey through accelerators and competitions
(00:31:18) Raising funds and extending runway through odd jobs
(00:40:45) Joining Paperspace and implementing product-led growth strategy
(00:54:33) Paperspace acquisition by Digital Ocean
(00:56:20) The experience of a successful exit
(01:02:22) Advice for non-technical professionals entering the tech industry
(01:04:00) Importance of curiosity in personal and professional growth
(01:09:58) Mental models for success in wrestling and sales
(01:12:35) Importance of repetition and constant refinement
(01:14:17) Turning unhappy customers into happy ones
(01:16:08) Transitioning from sales to product-led growth
(01:20:55) Navigating the stressful acquisition process with Paperspace
(01:24:30) Balancing ego and humility in leadership
(01:26:36) Hacking the fundraising process through alternative methods
(01:30:11) The moment the wire hit after the successful exit
(01:33:54) Staying at Paperspace post-acquisition and future plans
(01:38:02) Coolest use cases of AI seen in the past month
(01:41:56) Concerns about big players in the AI space and the need for regulation
Episode Links
Paperspace: https://www.paperspace.com/Digital Ocean: https://www.digitalocean.com/Meltwater Group: https://www.meltwater.com/enBen’s LinkedIn: https://www.linkedin.com/in/benjaminlamson/Jason Lemkin on having a mentor budget for VPs of sales: https://www.linkedin.com/pulse/do-your-vps-have-mentor-budget-jason-m-lemkin-2c/?trk=public_post
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/
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Aaron Lyles is the Founder and CEO of CommonAlly, a company that builds two-sided marketplaces to connect organizations with hard-to-reach communities in a way that empowers people and gives them agency over their data. Aaron's entrepreneurial journey began at a young age when he started a snowboarding magazine in high school despite challenges with ADHD. This experience taught him the value of passion, perseverance, and creative problem-solving. After college, Aaron founded a photography firm called Pixel Lab, which later evolved into a video production collective called Multiple Mammals.
The idea for CommonAlly was born out of Aaron's desire to create a more empathetic and less polarized world, especially for his young daughter, in the midst of the tumultuous 2016 election. He raised money from friends, family and dev firms to build the platform. Recently, CommonAlly was acquired by Small Great Ventures, allowing Aaron to continue pursuing his vision with the necessary resources and support. Throughout the interview, Aaron shares valuable insights and candid stories about the challenges of entrepreneurship, from difficult co-founder splits to navigating the acquisition process.
This episode is a must-listen for anyone interested in mission-driven entrepreneurship and the real-world challenges and triumphs of building a startup. Aaron's story offers an honest and inspiring look at the entrepreneurial journey, with lessons on resilience, adaptability, and staying true to one's values in the face of adversity. Aspiring founders and business leaders will come away with practical insights and wisdom they can apply to their own ventures.
Episode Outline
(00:00:00) Introduction
(00:03:47) Growing up with ADHD in the 80s and learning to navigate life differently
(00:05:12) Starting a snowboarding magazine in high school
(00:07:54) Overcoming academic struggles and getting into Emerson College
(00:10:21) Founding Pixel Lab photography business and evolving into Multiple Mammals
(00:17:07) Inspiration for starting CommonAlly during the 2016 election to combat polarization
(00:20:39) Challenges of being a solo founder and the importance of having the right partners
(00:25:34) Building a creative collective model with Multiple Mammals
(00:31:02) Pivoting CommonAlly's business model to focus on a two-sided marketplace
(00:37:29) Navigating the acquisition process with Small Great Ventures
(00:47:11) The role of AI in enhancing CommonAlly's offerings
(00:48:42) Lessons learned and advice for aspiring entrepreneurs
(00:52:36) Fundraising challenges and the importance of strategic partnerships for growth
(00:57:15) The evolution of CommonAlly's services
(01:02:54) The significance of CommonAlly's acquisition and the continuation of Aaron's vision
(01:06:09) The importance of mission-driven entrepreneurship and staying true to one's values
(01:11:42) Closing thoughts and how to connect with CommonAlly for potential partnerships
Episode Links
CommonAlly (current company): https://www.commonally.com/Multiple Mammals (previous company): https://www.multiplemammals.com/Small Great Ventures (acquired CommonAlly): https://www.smallgreat.co/Emerson College (attended): https://emerson.edu/
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Kat Hantas is the co-founder of 21 Seeds, an infused tequila brand that was acquired by Diageo for $160 Million after just three years in business, being the largest exit ever by a female-founded spirits brand. Previously, Kat had a 15-year career in the film industry, working at Creative Artists Agency and as an independent producer developing horror and music-driven films.
In this interview, Kat shares her entrepreneurial journey, from starting her first business right out of college to pivoting to a film career focused on specific niches to launching 21 Seeds to solve her own pain points around finding an easy-to-drink, low-calorie alternative to wine and cocktails. 21 Seeds differentiated itself by targeting a specific customer - women and moms - with an elevated, all-natural infused tequila. The brand took off quickly, landing national distribution in under two years.
Kat shares candid insights useful for entrepreneurs and business leaders, including the importance of focusing relentlessly on a specific customer, hiring people with complementary skills, building a culture of respect and results, and understanding the operational drivers in your business. This is a must-listen interview for anyone interested in consumer products, branding, entrepreneurship, and learning from a founder who defied the odds to build a category-creating brand and successful exit in record time.
Episode Outline
Here is a concise outline of the key topics discussed in the interview, with timestamps:
(00:00:00) Introduction and overview of Kat Hantas' background (00:04:13) Kat's childhood in Peru and moving to the US with her mother(00:11:07) Impact of seeing her mother's work ethic and hustle (00:14:39) Early entrepreneurial ventures and lessons learned (00:22:06) Working in the film industry after college (00:38:49) Challenges and ultimate failure of the movie "Taking Five" (00:48:26) Stepping back from work to focus on family and early motherhood(00:54:20) Health issues leading to switch from wine to infused tequila (01:03:08) Recognizing the market opportunity for elevated infused tequila (01:13:06) Launching 21 Seeds with her sister and co-founder in 2019 (01:15:58) Choosing Diageo as the acquirer for 21 Seeds (01:21:58) The intensive due diligence process leading up to acquisition (01:24:10) The emotional impact of the exit and concern for the team (01:30:40) Advice for building an excellent team with separate swim lanes(01:34:40) Dealing with copycats and the importance of speed to market(01:38:13) Reflections on the 21 Seeds journey and future plans
Episode Links
21Seeds (company co-founded by Kat Hantas): www.21Seeds.com21Seeds Instagram: www.instagram.com/21seedsKat’s Instagram: https://www.instagram.com/kathantas/Kat’s Linkedin: https://www.linkedin.com/in/kat-hantas-ba0621163/
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/
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Peter Thum is the Co-Founder and CEO of Muse, an AI-powered website builder and collaboration platform. He was previously the Founder of Ethos Water, which he successfully sold to Starbucks in 2005. Thum has also founded Fonderie 47, a company that transforms AK-47 assault rifles from African war zones into high-end jewelry and accessories, and Liberty United, which employs a similar model to reduce gun violence in the United States.
In this interview, Thum shares invaluable insights and experiences from his entrepreneurial journey, particularly the challenges and triumphs of building Ethos Water from a $10,000 startup to a major acquisition by Starbucks. He discusses the importance of bootstrapping, resourcefulness, and unwavering commitment to one's mission, even in the face of adversity. Thum also highlights the significance of strategic partnerships, as exemplified by his collaboration with Howard Schultz, which amplified the impact of Ethos Water and brought clean water access to millions of people in developing countries.
For young entrepreneurs, founders, MBA students, and managers, this episode offers a wealth of knowledge and inspiration. Thum's journey illustrates the importance of perseverance, adaptability, and the potential for businesses to drive positive social change. His experiences serve as a roadmap for navigating the complexities of building a mission-driven business while simultaneously making a meaningful impact on the world.
Episode Outline
(00:00:00) Introduction and overview of Peter Thum's background
(00:05:17) Peter's childhood in Korea and parents' careers
(00:09:39) Impact of losing his father at age 14
(00:14:01) Playing college football and being a team captain
(00:20:47) Early career at Gallo Winery and desire to move to Germany
(00:27:56) Decision to attend Kellogg School of Management
(00:32:39) Working at McKinsey & Company after business school
(00:44:43) Inspiration for Ethos Water during McKinsey projects
(01:03:21) Bootstrapping and launching Ethos Water
(01:18:27) Getting Ethos Water into Whole Foods and Starbucks
(01:32:13) Selling Ethos Water to Starbucks
(01:43:40) The social impact of Ethos Water with Starbucks' reach
(01:50:45) Founding Foundry 47 to transform AK-47s into luxury items
(01:56:03) Creating Liberty United to reduce gun violence in the US
(01:58:58) Co-founding Muse, an AI-powered no-code platform
(02:05:01) Muse's vision to democratize tech for all skill levels
Episode Links
Ethos WaterStarbucksFonderie 47 (founded by Peter Thum)Liberty United (founded by Peter Thum)Muse (current company, co-founded by Peter Thum)McKinsey & Company (former employer)Gallo Winery (former employer)Kellogg School of Management (alma mater)
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/
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Lindsey Andrews is the founder of Minibar, an on-demand alcohol delivery service that was acquired by Reserve Bar in 2021. Andrews is now the Founder and CEO of Revido, an app designed to revolutionize the way we review and recommend products and services.
Andrews' entrepreneurial journey began when she and her co-founder recognized the need for a convenient alcohol delivery service during their "takeout tuesdays," leading to founding the online alcohol delivery service, MiniBar. Throughout the interview, Andrews shares valuable insights and experiences from her entrepreneurial journey that led to Minibar’s acquisition. She discusses the challenges of navigating the highly regulated alcohol industry and the importance of having a strong network of advisors and investors. Andrews also touches on the difficulties of fundraising as a first-time entrepreneur and a woman in a male-dominated industry.
This episode is a must-listen for aspiring entrepreneurs, founders, MBA students, and managers. Andrews' journey is an excellent example of how to navigate the challenges of building a successful startup in a highly regulated industry. Her insights on fundraising, team building, and work-life balance are invaluable for anyone looking to start or grow a business. Additionally, her experience with the acquisition of Minibar and her decision to start a new venture provide a unique perspective on the different paths entrepreneurs can take after a successful exit.
Episode Outline
(00:00:00) Introduction
(00:02:58) Lindsey Andrews' upbringing and early exposure to business
(00:07:07) Educational journey at Stanford and Wharton
(00:10:11) Early career experiences at Fresh Direct, Amazon, and Quidsi
(00:15:30) Aha moment and founding Minibar
(00:20:15) Navigating regulatory challenges in the alcohol delivery industry
(00:23:18) Fundraising challenges and lessons learned
(00:26:05) Building a strong team and leveraging outsourced talent
(00:30:39) Positioning and marketing strategies for Minibar
(00:35:41) Losing a term sheet and managing cash burn during difficult times
(00:42:44) Balancing entrepreneurship and motherhood
(00:45:41) Growth and impact of COVID-19 on Minibar's business
(00:49:52) Decision to sell Minibar and the acquisition process
(00:53:38) Taking time off and deciding to start a new venture, Revito
(00:58:17) Inspiration behind Revido and challenges of building a new startup
(01:02:59) Fundraising for Revido and current challenges
(01:08:12) Lindsey's daughter's perception of her as an entrepreneur
(01:11:08) Conclusion and key takeaways for aspiring entrepreneurs and founders
Episode Links
Minibar - Lindsey Andrews' on-demand alcohol delivery startup
Revido - Lindsey Andrews' new venture focused on trusted recommendations
Reserve Bar - The company that acquired Minibar in 2021
Fresh Direct - Lindsey Andrews worked here prior to founding Minibar
Support & Connect
Forward Obsessed Website: www.forwardobsessed.com
Instagram: https://www.instagram.com/forwardobsessed/
TikTok: https://www.tiktok.com/@forwardobsessed
LinkedIn: https://www.linkedin.com/showcase/forward-obsessed/
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Jason Kirby is the Founder of Thunder.VC, an AI-powered investment bank that helps startups navigate the fundraising process. Previously, he was the Co-Founder and President of Liquid Sky, a cloud gaming company acquired by Walmart in 2018, and the President and COO of Generation Esports, an esports platform for schools that raised $11 million in funding.
Throughout the interview, Kirby shares valuable insights and lessons learned, such as the importance of setting deal terms before diving into due diligence, focusing on customer acquisition instead of fundraising, and the challenges of managing investor expectations. He also discusses his experience thriving in chaos and his ability to align teams towards a common goal.
Kirby's story is one of resilience, adaptability, and perseverance in the face of numerous challenges and setbacks. He emphasizes the value of learning from failure, building strong relationships, and staying committed to one's vision. His journey from photographer to successful tech founder and investor is an inspiration for aspiring entrepreneurs.
This episode is a must-listen for anyone interested in the world of startups, fundraising, and entrepreneurship. Kirby's firsthand accounts of navigating acquisitions, pivoting business models, and managing team dynamics provide invaluable lessons for founders, MBA students, and managers alike. His story serves as a reminder that success often comes from embracing chaos, learning from failure, and never giving up.
Episode Outline
(00:00:00) Introduction and sponsorship messages(00:03:15) Jason Kirby's early entrepreneurial journey and photography business(00:10:32) Launching San Diego Photography Classes and the importance of asking questions(00:15:19) Transitioning from photographer to business person with Toggly marketplace(00:23:09) Raising capital for Togally and the importance of targeting the right investors(00:26:25) Almost getting acquired by Kodak and lessons learned(00:29:40) Joining Liquid Sky as Co-Founder and raising $12 million(00:36:17) Samsung's acquisition offer and the deal falling through(00:41:15) Pivoting Liquid Sky's business model and securing enterprise contracts(00:43:44) Getting acquired by Walmart and the stressful acquisition process(00:49:54) Becoming a Walmart employee and the shutdown of the gaming project(00:51:51) Consulting for Generation Esports and helping them scale(00:56:56) Raising funds for Generation Esports and navigating the COVID-19 pandemic(01:02:45) Leaving Generation Esports due to differences in vision(01:05:04) Founding Thunder.VC and building an AI-powered investment bank(01:09:16) Identifying people who thrive in chaos and the importance of perseverance
Episode Links
Thunder.VC: https://web.thunder.vc/Jason Kirby's Twitter: https://twitter.com/jasonkirbyJason Kirby's LinkedIn: https://www.linkedin.com/in/jasonrkirby/Rich Dad Poor Dad by Robert Kiyosaki (Book): Amazon LinkJason Kirby's podcast: Fundraising Demystified
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Jess Lynch is currently the Cofounder and Founding Partner at Raiz Capital, an early-stage venture capital firm using data and community to reimagine startup investing. She was previously the Cofounder and CEO of Wishroute, a scalable behavior change platform that was acquired in 2022.
Throughout her journey, Jess has demonstrated remarkable resilience and leadership. This includes overcoming challenges like running out of cash and weathering the pandemic's impact on Wishroute's initial customers. She successfully led her company through an M&A process despite a difficult experience with one large potential acquirer. Jess credits her success to intuition, problem-obsession, and genuinely caring for people.
The interview touches on many topics valuable to founders and business leaders. Jess emphasizes the importance of having a technical co-founder or trusted advisor early on. She shares recommendations for managing fear, getting comfortable with discomfort, and pushing past the limits of your comfort zone. Additional insights include lessons learned from fundraising, managing investor relationships, preparing for acquisition, and running an accelerator program.
A key theme is Jess' remarkable perseverance and her development of an innate sense for when to push forward versus when it's time to change course. Her story demonstrates that entrepreneurial success requires hard work and also an element of luck or good timing. Overall, Jess Lynch provides a wealth of practical knowledge and inspiration for anyone interested in startups, venture capital, or leadership. This is a must-listen episode packed with forward-thinking wisdom.
Episode Outline
(00:00:00) Introduction(00:02:06) Early entrepreneurial interests and family backdrop(00:05:31) Brother's juvenile diabetes diagnosis inspires family lifestyle changes(00:07:16) Educational background at Babson College(00:10:59) Early career in forensic accounting at PwC(00:15:33) Leaving corporate career to pursue entrepreneurial path(00:18:22) Working on BP oil spill litigation(00:23:32) Finding the idea for Wishroute while at Babson MBA program(00:25:37) Launching Wishroute and early traction(00:27:34) Pandemic causes pivot from gyms to direct-to-consumer(00:30:58) Fundraising challenges as a female founder without technical background(00:32:04) Mental health during startup struggles and running out of cash(00:36:41) Large potential acquirer ends up building internally instead(00:42:26) Emotionally difficult decision to pursue acquisition of Wishroute(00:43:04) Warning signs when deal-making with large companies(00:44:51) Importance of letter of intent in M&A process(00:47:19) Securing acquisition despite numerous setbacks(00:49:20) Lifelong lessons in resilience from journey(00:50:07) Reluctance to jump back into startup founder role after acquisition(00:53:30) Currently supporting portfolio companies and investing in CT
Episode Links
Wishroute (founded by Jess Lynch): https://www.wishroute.com/
Raiz Capital (co-founded by Jess Lynch) https://raiz.vc/
Babson College: https://www.babson.edu/
Techstars: https://www.techstars.com/
Suggestic: https://suggestic.com/
Guidely: https://guidely.com/
Jessica Lynch on LinkedIn: https://www.linkedin.com/in/jessicallynch/
Jessica Lynch on TikTok: https://www.tiktok.com/@jessicallynch
Lenny's newsletter - https://www.lennysnewsletter.com/
The Lean Startup book - https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898
Brian Chesky episode on Lenny's newsletter - https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
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/
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Adi Eckhouse Barzilai is the Co-Founder and CEO of RealFace, a facial recognition software company that was acquired by Apple Inc. She was previously in brand management at Procter & Gamble. As founder of RealFace, Adi helped pioneer mobile facial recognition capabilities that later became integral to Apple’s FaceID unlock feature. RealFace provided the core IP and engineering talent behind making robust facial authentication seamless for iPhone users worldwide. After multiple pivots and surviving high-stakes fundraising stresses familiar to most early-stage founders, Adi successfully negotiated an acquisition deal with Apple.
Throughout a wide-ranging interview, Adi shares hard-won lessons from her entrepreneurial journey in the high-risk world of consumer tech startups. For young founders, she strongly advocates getting hands-on experience learning computer science to better grasp future opportunities. Adi also believes time working at a top corporation exposes priceless insights on how elite marketing, product development, and operational scale-up works behind the scenes.
Episode Outline
(00:00:00) Introduction
(00:02:00) Adi's background and early entrepreneurial influences
(00:06:00) Studying computer science and working at Procter & Gamble
(00:10:00) Getting an MBA from Columbia Business School
(00:14:00) The importance of branding for startups
(00:17:00) Adi's thoughts on MBAs and issues of antisemitism on campus
(00:20:00) The hostage crisis in Gaza
(00:23:00) Defining what a brand is
(00:26:00) Why investing in brand matters for startups
(00:30:00) Pivoting RealFace from a consumer app to facial recognition
(00:35:00) The challenges of being a startup founder/CEO
(00:40:00) Having the entrepreneurial "bug" and the importance of co-founders
(00:45:00) Differentiating between tech and product companies
(00:48:00) The niche strategy behind RealFace's technology
(00:55:00) Connecting with Apple and maintaining secrecy
(01:00:00) Negotiating the acquisition deal with Apple
(01:05:00) The emotional rollercoaster of the startup journey
(01:10:00) Adi's feeling when the Apple acquisition closed
(01:15:00) Trying to launch a nonprofit after the exit
(01:20:00) Why Adi is passionate about education and empowering girls
Episode Links
Procter & Gamble (former employer): https://us.pg.com/
RealFace (Co-Founder and CEO): https://www.timesofisrael.com/apple-buys-israels-facial-recognition-firm-realface-report/
Adi’s Linkedin: https://www.linkedin.com/in/adi-eckhouse-barzilai-8000928/
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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/
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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/
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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/
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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 LinksMediaocean: 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 & ConnectDigital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/
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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 LinksAndre’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.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/ -
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 onlineEpisode 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/160145855XGet Out of Your Way (Book): https://www.amazon.com/Get-Out-YOUR-Jared-James/dp/1633672786Podcast Info
Podcast website: https://forwardobsessed.com/Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4zYouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWqlSupport & Connect
Digital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/ -
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/nijhawhatMenda Health: https://www.menda.health/PODCAST INFO:
Podcast website: https://forwardobsessed.com/Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4zYouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWqlSUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/ -
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/0977959619Into the Forest (book about Alan's mother by Rebecca Frankel): https://www.amazon.com/Into-Forest-Holocaust-Survival-Triumph/dp/1250267641PODCAST INFO:
Podcast website: https://forwardobsessed.com/Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4zYouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWqlSUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/ -
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 servicesEPISODE LINKS:
Wiley’s LinkedIn: https://www.linkedin.com/in/wileycerilli/Wiley’s Twitter: https://twitter.com/wileycerilli?lang=enSeamless Web: https://www.seamless.com/SinglePlatform: https://my2.singleplatform.comGood Uncle: https://www.gooduncle.com/Experience Camps: https://experiencecamps.org/David and Goliath Book: https://www.amazon.com/David-Goliath-Underdogs-Misfits-Battling/dp/0316204374Thinking Fast and Slow Book: https://www.amazon.com/Thinking-Fast-and-Slow-audiobook/dp/B005Z9GAJGThe 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/id1615760781Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4zYouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWqlSUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/ -
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 peopleEPISODE 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/TLMLinkedIn Page: https://www.linkedin.com/company/the-last-mile/Youtube: https://www.youtube.com/channel/UCxnslwxnp3acFh13V-uvvJQChris’ Twitter: https://twitter.com/chrisredlitzChris’ 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/id1615760781Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4zYouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWqlSUPPORT & CONNECT:
Digital Surgeons Website: https://digitalsurgeons.comTikTok: https://www.tiktok.com/@digitalsurgeonsInstagram: https://www.instagram.com/digitalsurgeonsLinkedIn: https://www.linkedin.com/company/210497/ - Visa fler
