Alex Lieberman, co-founder of Morning Brew and host of the Founders Journal podcast, takes us on a whirlwind journey through his post-exit adventures. From getting a full-body MRI to launching a quirky backyard game, Alex candidly shares the highs and lows of life after a successful startup. He delves into Morning Brew's evolving content strategy, the future of marketing, and the challenges of finding product-market fit with his new venture, StoryArb. Filled with relatable stories and valuable insights, this conversation is a must-listen for entrepreneurs at any stage looking to stay innovative and adaptable in an ever-changing business landscape.00:00:00 - Intro00:09:13 - Alex's Failed Plunger Game00:11:58 - Humanizing Brands00:14:52 - Expectations on public-facing CEOs00:17:06 - Hiring young, agile marketing talent00:21:12 - Zero to one: Alex's creative drive00:24:28 - StoryArb00:26:39 - Lessons learned from StoryArb00:30:18 - Morning Brew's evolving content strategy00:32:00 - Creator Economy00:40:10 - Challenges in the content market00:42:40 - Early-stage startups as challenging customers00:43:20 - Four points of value for CEOs00:44:00 - Outsourcing: From odd to essential00:45:22 - Wrap-upAlex's StuffWebsite: https://foundersjournalpod.morningbrew.com/X: https://x.com/businessbaristaLinkedIn: https://www.linkedin.com/in/alex-lieberman/My StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

Jason Kirby shares hard-earned wisdom with Connor, from exiting his company to Walmart, after a failed acquisition by Samsung. Jason explains key lessons for founders in the acquisition process, like getting your own legal counsel and maintaining multiple options. He also details his new venture Thunder, an investment bank aiming to provide founders with the M&A and fundraising guidance he wished he had.The two discuss the rise of eSports in schools, navigating the stresses of being an acquisition target while running a company, and the importance of surrounding yourself with the right advisors.Subscribe for more behind-the-scenes insights on entrepreneurship and life after an exit. Check out the links to connect with Jason and access Thunder's free investor matching tool for founders.Chapters:00:00:00 - Introducing Jason Kirby00:02:30 - What Thunder Offers to Founders00:04:55 - The Challenges of Raising Capital00:07:56 - Building Thunder00:13:13 - Bringing eSports to Schools00:22:49 - The Rollercoaster of Selling Liquid Sky00:29:12 - Picking Up the Pieces00:32:07 - Maintaining Optionality00:34:53 - Hard Lessons Learned from M&A00:41:57 - The Rise of Solo GP00:45:32 - Wrapping UpJason Kirby's StuffWebsite: https://web.thunder.vc/X: https://x.com/JasonKirbyLinkedIn: https://www.linkedin.com/in/jasonrkirby/My StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

In this episode, we sit down with Luke Bonney, co-founder of Redox, a healthcare tech company that raised $95 million. Join us as Luke shares his journey from med school dropout to successful entrepreneur, discussing the challenges of building a startup, the importance of strong co-founder relationships, and the future of healthcare technology. Tune in for valuable insights and lessons learned from a founder who's been in the trenches.00:00:00 - Intro00:05:07 - The Power of a Big, Bold Purpose00:07:08 - Building a Distributed Company at Redox00:10:04 - Challenges of Handling Healthcare Data00:11:16 - Stepping Down as CEO00:15:07 - Adapting to Different Phases of Life00:18:12 - Maintaining Strong Co-Founder Relationships00:22:13 - Post-Exit Lifestyle00:24:22 - Leadership Principles00:29:17 - Working On the Company00:34:43 - AI in Healthcare00:36:01 - Start-Ups Changing Landscape00:37:12 - Better Support SystemsLuke's Stuff:LinkedIn: https://www.linkedin.com/in/luke-bonney-he-him-965a135/My StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

From celebrity crashes to influencer insights, lessons from a marketing pioneer. Join Connor Tomkies as he sits down with Gil Eyal, a serial entrepreneur who's seen it all in the world of influencer marketing. Discover the ups and downs of Gil's journey, from working with A-listers like Lil Wayne and Leonardo DiCaprio to navigating the ever-changing landscape of social media.Packed with valuable insights on leveraging celebrity partnerships, adapting to data restrictions, and the future of influencer marketing, this episode is a must-watch for anyone looking to make their mark in the digital world.[00:00:00] - Gil Eyal's Celebrity Crash Course[00:04:19] - Pivoting from Mobli to Hypr[00:06:55] - The Social Network Data Goldmine[00:09:05] - Cambridge Analytica: The Turning Point[00:11:13] - The Acquisition Roller Coaster[00:13:40] - Structuring Celebrity Equity Deals[00:18:25] - The Power of the Number Two Position[00:22:13] - The Jake Paul Effect: Influencer Boxing[00:24:29] - The Micro-Influencer Debate[00:28:48] - Soho House: Exclusivity vs. Scalability[00:32:31] - The Rise of Community-Focused Real Estate[00:37:17] - Finding Opportunities in Underutilized Assets[00:43:47] - The Game-Changing Potential of Medical Weight Loss[00:47:46] - Wrap-up and Contact InfoGil's Stuff:https://stardustventures.us/gil@stardustventures.usMy StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

Entrepreneur Shane Neman shares his incredible journey from founding Junebug, a nightclub software and events company, to building EZ Texting, a pioneering mass texting platform. Discover how Shane spotted opportunities, pivoted when necessary, and bootstrapped his way to success. He also shares insights into his current ventures, including an investment in humanoid robotics and the acquisition of the iconic Santa Monica Pier.00:00:00 - Intro00:01:00 - Junebug's Origins00:04:05 - Launching Junebug00:07:20 - Hosting Events00:10:30 - Junebug's Success00:12:51 - The Texting Opportunity00:16:07 - Transitioning to EZ Texting00:19:50 - EZ Texting's Acquisition00:23:05 - Starting Neman Ventures00:25:10 - Investing in AI Robotics00:27:40 - Acquiring the Santa Monica Pier00:29:15 - ConclusionShane Neman Stuff:Website: https://www.shaneneman.com/X: https://twitter.com/shanenemanLinkedIn: https://www.linkedin.com/in/shanenemanInstagram: https://www.instagram.com/shaneneman/YouTube: https://www.youtube.com/@shanenemanFacebook: https://www.facebook.com/NemanVentures/My StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

Serial entrepreneur Adam Spector shares his journey of building and exiting multiple startups, including his current venture, Levy, which revolutionizes back-office support. In this engaging episode, Adam discusses the lessons he's learned from navigating the entrepreneurial rollercoaster, the importance of solving real problems, and his outlook on the future of work in an era of AI and globalization. He also shares insights on running a VC-backed vs. bootstrapped company, the challenges of attribution in personalization, and the increasing accessibility of entrepreneurship. Tune in for a candid conversation filled with valuable advice for entrepreneurs at any stage of their journey.00:00:34 - Adam's Background00:01:17 - Starting Levy00:02:36 - Solving Real Problems00:07:10 - Running a Startup00:09:10 - Growing the Business00:10:37 - Spinning Out Levy00:13:37 - Adam's Four Startups00:19:16 - Missed Acquisition00:23:35 - Building & Selling Lift Igniter00:28:32 - VC vs. Bootstrapped00:32:26 - Future of Work Outlook00:40:06 - AI in Outsourcing00:41:16 - Accessible Entrepreneurship00:42:46 - Reflections on SuccessAdam Spector's StuffAdam's Business:  https://www.levy.company/X: https://x.com/aspec00?s=20LinkedIn: https://www.linkedin.com/in/adamspector2My StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

Join along as I sit down with the incredibly inspiring Vlada Lotkina, the brain behind ClassTag, for a journey filled with dreams, determination, and the drive to make a difference in the world of education. From her early days in Ukraine to creating waves in the U.S. tech scene, Vlada's story isn't just about building a successful platform; it's about bridging gaps, overcoming the naysayers, and transforming challenges into triumphs. We're not just sharing her success story; we're diving into the essence of what it means to pursue your passions, stand up after setbacks, and forge your path in the world. Whether you're an aspiring entrepreneur or someone who loves a good story of hope and hard work, you won't want to miss this.[00:00:00] Introduction[00:01:03] Founding ClassTag[00:03:04] Vlada's Entrepreneur Background[00:06:04] Navigating business during the war in Ukraine[00:09:56] Selling ClassTag[00:12:47] Reflecting on the Exit[00:15:39] After the Exit[00:17:28] Supporting Immigrant Founders[00:23:33] Scaling ClassTag to 5 million users[00:27:44] Impact of COVID on ClassTag's Growth[00:31:21] Parenting and Entrepreneurship[00:37:22] Wrap-upVlada Lotkina's StuffWebsite: https://www.elev8orlab.com/X: https://twitter.com/vlotkinaLinkedIn: https://www.linkedin.com/in/vlada-lotkinaMy StuffPodcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

We dive into the journey of Benji Markoff, a visionary entrepreneur who transformed the insurance industry with his startup, Founder Shield. Benji shares his rollercoaster experience from the early days of grueling work and personal challenges to achieving a monumental exit. Listeners will gain insights into the importance of resilience, innovation, and the unexpected paths of entrepreneurship, as well as a peek into his next venture, revolutionizing wellness and beyond.[00:00:00] Opening[00:01:01] Intro[00:06:09] Founding Founder Shield[00:13:29] The Acquisition Gauntlet[00:20:28] Keys to Startup Success[00:27:59] Life After Exit[00:33:51] Establishing a Family Office[00:40:31] Investing in Tangible Businesses[00:44:03] Discovering Padel Sport[00:51:32] Creating a Social Wellness Club[00:56:09] OutroBenji's Stuff:Website: https://www.sja58.com/Padel United Sports Club: https://www.padelunitedsportsclub.com/LinkedIn: https://www.linkedin.com/in/benjimarkoff/My Stuff:Podcast: MadeItPod.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

LISTENER NOTE: My Second Million asa title was always intended as a cheeky joke around the fantastic pod "My First Million" but now on April Fools we've decided to pivot as so many founder do, to the "Made It with Connor Tomkies" podcast. We can't wait for the guests we have coming up and we're excited to share more episodes. Stay tuned for more episodes of "Made It with Connor Tomkies"  Dive into an enlightening conversation with Aaron White, a tech visionary who recently sold two companies, ProfitWell and Blissfully, in a remarkable dual exit. In this episode, Aaron opens up about the rollercoaster journey of entrepreneurship, from confronting massive industry pushback to experiencing the life-changing moments of selling his ventures. Tune in to uncover the real challenges and triumphs behind building and selling a startup, and what life holds on the other side of success.Aaron's StuffAaron's Blog: https://www.singularity.vc/ X: https://x.com/aaronwhite?s=20 LinkedIn: https://www.linkedin.com/in/aaronmwhite/My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

Connor dives deep with Jeremy Parker, the innovative mind behind Swag.com. They explore Jeremy's dynamic journey from aspiring filmmaker to successful entrepreneur. Jeremy shares the highs and lows of his entrepreneurial path, revealing how he navigated through failures and pivots to build and sell swag.com, transforming the promotional products industry along the way. This episode offers a unique look into the strategies, mindset, and resilience required to turn visionary ideas into profitable ventures.00:00:00 Chapter 1: The Entrepreneurial Journey00:03:18 Chapter 2: Innovating in Promotional Products00:08:23 Chapter 3: Acquisition Insights00:13:51 Chapter 4: The Birth of Swag.com00:19:53 Chapter 5: Strategies for B2B Success00:25:34 Chapter 6: Launching SwagSpace00:31:17 Chapter 7: Post-Exit ReflectionsJeremy's StuffWebsite: https://swag.com/X: https://x.com/yocanikickit?s=20LinkedIn: https://www.linkedin.com/in/jeremyianparker/My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

In this episode host Connor Tomkies sits down with the seasoned entrepreneur, podcaster, and founder of Mixergy, Andrew Warner, to explore the intricacies of entrepreneurship in the digital age. They delve into the critical role of becoming a micro-influencer as an entrepreneur, share personal journeys of business successes and lessons learned from failures, and discuss the strategic advantages of outsourcing and harnessing international talent. The conversation also touches on future trends, including the potential of service-based business models and the significance of content creation and influencer marketing in scaling businesses.[00:00:00] Chapter 1: Introduction to Entrepreneurial Influence[00:03:17] Chapter 2: The First Million: Strategies and Paranoia[00:08:11] Chapter 3: Evolution of Email Marketing and Co-Reg[00:10:47] Chapter 4: From Failed Ventures to Dog Genetics Success[00:13:32] Chapter 5: Building and Scaling Support Ninja[00:17:08] Chapter 6: Future Ideas and International Hiring[00:20:07] Chapter 7: The Ongoing Journey of Mixergy[00:23:38] Chapter 8: Service-Based Business Success Stories[00:26:21] Chapter 9: Assembling Your Marketing Department[00:29:12] Chapter 10: The Importance of Being a Public Founder[00:31:24] Chapter 11: Entrepreneurial Investments and Founder.org[00:32:51] Chapter 12: Closing Remarks and Future PlansAndrew's StuffPodCast Site: https://podflow.com/Andrew's Site: https://mixergy.com/Andrew's X: https://x.com/AndrewWarner?s=20Andrew's Book: https://www.amazon.com/Stop-Asking-Questions-High-Impact-Interviews/dp/1737676540My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/ X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/