Host Callan Harrington breaks down the careers of top founders and executives, pulling out the key items that led to their success. These are actual career transitions, mistakes, insights, breakthroughs, and general advice that can be immediately implemented.
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Matt Farrell - COO at Niobium Microsystems: Succeeding in the Earliest Stages, Evaluating Potential Employees, and Creating Work/Life Alignment
43:05
43:05
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43:05Matt Farrell is the COO at Niobium Microsystems, a trusted hardware design company developing high-performance microelectronic components to enable the secure collection, processing, and distribution of critical data. Matt is a multi-time founder and early-stage executive. Before the startup world, Matt was a coach for the University of Dayton Men’…
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Mastering Content Strategy, Delegation, and Creative Efficiency
20:51
20:51
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20:51In this episode of That Worked, co-hosts Callan Harrington and Sullivan Finlay dive into content strategy, delegation, and maximizing creative output. Sullivan shares how structured planning has transformed his workflow, the power of visual content boards, and why repurposing content is essential for expanding reach without reinventing the wheel. T…
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The Power of Improv, AI-Driven Content, and Buying Back Time for Growth
23:28
23:28
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23:28In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay explore how improv can transform leadership, the evolving landscape of AI-driven content creation, and why outsourcing is essential for scaling creative work. Sully shares improv techniques—such as adaptability and active listening—that boost effecti…
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The Ethics of AI, Digital Likenesses, and the Future of Content Creation
26:39
26:39
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26:39In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay dive into the rapidly evolving role of AI in entertainment, content creation, and brand collaborations. They explore the ethical dilemmas of AI-generated personas, the impact of deep research tools on competitive analysis, and how AI is reshaping cre…
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Callan Harrington, Founder of FlashGrowth and host of That Worked, takes a deep dive into the strategic decision to niche his business into the insurance space. In this solo episode, he breaks down the fears, challenges, and long-term benefits of narrowing focus in business. If you’ve ever hesitated to specialize, this episode is packed with insigh…
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The Power of Niching Down, Adding Instant Value, and Vulnerability in Content Creation
30:22
30:22
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30:22In this episode of That Worked, host Callan Harrington and co-host Sullivan Finlay, a writer, comedian, and content creator, dive into the challenges and opportunities of building a career in the evolving digital landscape. They explore the vulnerability of content creation, why niching down can accelerate business growth, and how relationship-buil…
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Sriya Maram - Co-Founder of Persana AI: The Modern GTM Stack, Prompt Engineering, and How AI is Impacting GTM
36:23
36:23
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36:23Sriya is the Co-Founder of Persana AI. Persana AI is a Y-Combinator-backed AI tool designed to enhance sales through hyper-personalization, seamless integration, and united workflows. Prior to Persana AI, Sriya was a Product Manager at LinkedIn. In this episode, you’ll learn: The value of participating in hackathons. What a modern GTM tech stack lo…
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Scott Knowles - Co-Founder and CEO of Deep Vector: Empathy in Sales, Selling to a Competitor, and Breaking the Rules
34:48
34:48
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34:48Scott Knowles is the Co-Founder and CEO of Deep Vector, a web-based software platform that transforms unstructured documents into actionable insights with speed and precision. Prior to Deep Vector, Scott was the Founder and CEO of Modgic, a software company that provided workers' compensation and mod analysis tools for the commercial insurance indu…
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Dan Snyder - CEO & Co-Founder of Lower: Launching a B2C Line, Growth through Acquisition, and Building an Entrepreneurial Culture
30:11
30:11
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30:11Dan Snyder is the CEO & Co-Founder of Lower, a multi-channel home lender he helped build and grow over the last decade into the 28th largest lender in the country. Lower operates both an online direct to consumer business, and offline retail business with over 150 offices across the country. Lower raised the largest Series A in the State of Ohio ($…
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Tom Grote - CEO of Agape Automation: Narrowing your Focus, Stong Values, and Balancing the Core Business and Innovation
31:05
31:05
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31:05Tom Grote is the CEO of Agape Automation, a food-tech innovation company that creates the automated Smart Kitchens of the future. Prior to Agape Automation, Tom was the COO of Donatos Pizza for over 17 years, a family-owned pizza company with more than 150 locations in six states. In this episode, you’ll learn: How narrowing in on what you’re reall…
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Dan Manges - Co-Founder of RWX: Finding Your Co-Founder, Engineering Challenges, and Decision Making
47:24
47:24
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47:24Dan Manges is the Co-Founder of RWX. RWX develops software engineering tools that optimize build and test performance, reliability, and developer experience. Its flagship product, Mint, is a generation newer Continuous Integration platform that gives engineers unparalleled capabilities to optimize their builds. Dan was previously the CTO of Root, a…
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Matthew Achak - Co-Founder of FCR: Coin Flips, Choosing the Right Business Partner, and Employee Retention
34:11
34:11
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34:11Matthew Achak is the Co-Founder and Managing Partner of Non-Linear Venture Partners, where he consults and invests in early-stage start-ups. Prior to Non-Linear Venture Partners, Matt Co-Founded FCR, the leading provider of outsourced live agent support services for tech companies. FCR was acquired by TTEC in 2019. In this episode, you’ll learn: Th…
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David McFarland - Founder and CEO of Coterie Insurance: Building the Initial Team, Mitigating Hiting Mistakes, and Stage Fit
37:33
37:33
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37:33David McFarland is the Founder and CEO of Coterie Insurance. Coterie Insurance puts insurance agents and brokers first, delivering instant business insurance across the United States. Since 2018, Coterie has raised over $100M in funding and partnered with over 10,000 insurance agencies and brokerages across the country. Prior to leading Coterie, Da…
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Ry Walker - Founder and CEO of Tembo: Difficult Moments, The Role of CEO, and Paying it Forward
28:03
28:03
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28:03Ry Walker is the Founder and CEO of Tembo. Tembo is the Postgres developer platform for building every data service. Their mission is to collapse the database sprawl of the modern data stack with a unified developer platform. Prior to founding Tembo, Ry was the Founder and CEO of Astronomer, which has been a huge success and has raised over 280 mil…
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Todd Kaufman - Co-Founder and CEO of Test Double: ESOPs, Strict Profit Margins, and Building an Ownership Mentality
43:54
43:54
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43:54Todd Kaufman is the Co-Founder and CEO of Test Double. Test Double is a software agency offering consulting services in development, product management, and infrastructure. Their experienced consultants embed with your team and help solve problems from strategy to execution. Todd has been a software engineer for over 25 years, focusing on building …
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Joe Apgar - CEO of PELOTONIA: Surviving Cancer, Sharing Your Story, and the Power of Family and Friends
56:40
56:40
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56:40Joe Apgar is the CEO of PELOTONIA, which was established in 2008 to fund lifesaving cancer research and is a rapidly growing non-profit today. Before PELOTONIA, Joe worked eight years at Rockbridge Capital. He was named to the 40 Under 40 Class of 2020 by Columbus Business First and the Future 50 Class of 2021 by Columbus CEO Magazine. In 2022, he …
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Maddie Bell - Co-Founder and CEO of Scheduler AI: Driving Habit Change, Using Your Own Product, and Big Idea Thinking
40:37
40:37
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40:37Maddie Bell is the Co-Founder and CEO of Scheduler AI, an AI appointment setter that integrates directly into your CRM, web forms, and chats to coordinate meeting times in seconds while safeguarding your show rates. Prior to Scheduler AI, Maddie was a Brand Director for Procter & Gamble. While at P&G, she spent 12 years leading and delivering topli…
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Aaron Crookes - Co-Founder & CEO of Apricity Robotics: Picking the Right Product for Your Market, Balancing Product Development vs. Business Building, and Strategic vs. Generalist Investors
35:39
35:39
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35:39Aaron Crookes is the Co-Founder and CEO of Apricity Robotics, a startup focused on developing semi-autonomous robots to aid and assist both patients and healthcare staff. Their main goal is to automate simple tasks so healthcare staff can be fully dedicated to critical patient needs. Prior to Apricity Robotics, Aaron worked in R&D for Autonomous Ro…
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Amanda Epp - CEO at ScriptDrop: Creating a Network Effect, Building a Customer Flywheel, and Being Your Authentic Self as CEO
40:34
40:34
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40:34Amanda Epp is a founding team member and the CEO of ScriptDrop. ScriptDrop is the only healthcare IT company specializing in medication access that serves patients in all 50 states. ScriptDrop works alongside its healthcare partners to deliver medication access opportunities through technology, empathy, and healthcare expertise. Previously, Amanda …
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Genevieve Bellaire - Founder & CEO of Realworld: Transitioning from B2B to B2C, Launching a Zero to One Product, and Creating a Category
37:08
37:08
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37:08Genevieve Bellaire is the Founder and CEO of Realworld. Realworld is your companion for navigating the journey of adulthood. They help you "get it together" by simplifying and streamlining your finances, health, career, and household. Prior to Realworld, Genevieve received her JD and MBA from Georgetown University and spent time at Goldman Sachs be…
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Brian Gregory - Co-Founder and CEO of FMX: Waiting to Raise Capital, CEO Transitions, and Going Outbound
43:02
43:02
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43:02Brian Gregory is the Co-Founder and CEO of FMX. FMX is a leading provider of purpose-built, cloud-based solutions for Public Sector organizations. They help their customers transform facility, maintenance, and operations management in the communities where everyone learns, works, and lives. Before founding FMX, Brian was a partner at Dynamix Energy…
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Lindsay Fork - Founder & CEO of Luxe Brands: Turning Challenges into New Businesses, Filtering Opportunities, and EOS
41:38
41:38
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41:38Lindsay Fork is the Founder and CEO of Luxe Brands. Luxe Brands is a bridal fashion company with multiline offerings + brands for all brides. From La Jeune Mariee Bridal Collection, a luxury designer and special-order boutique located in downtown Columbus, Ohio, to "luxury for less" with multiunit Luxe Redux, the company caters to serve all brides.…
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Chris Powell - CEO of Talmetrix: Red Pill Moments, Going from Corporate to Startup, and Channel Partnerships
38:08
38:08
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38:08Chris Powell is the CEO of Talmetrix, an employee feedback and analytics company with a mission to humanize data to further workplace well-being. Leading up to Talmetrix, Chris built a career in human resources, including working as the Chief Human Resources Officer for Scripps Networks Interactive. In this episode, you’ll learn: How to capitlize o…
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Tsavo Knott - Co-Founder and CEO of Pieces: Building a Community, Trusting your Gut, and Company Events
34:17
34:17
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34:17Tsavo is the CEO and Co-Founder of Pieces, a suite of on-device developer tools that boost productivity by helping you solve complex development tasks through a contextual understanding of your entire workflow. Tsavo was an entrepreneur from the jump, founding his first company, accent.ai, straight out of high school. In this episode, you’ll learn:…
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Exploring 10X Goals, Navigating Creativity, Content Optimization, and Delegation Strategies
33:08
33:08
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33:08Callan Harrington is the founder of Flashgrowth, and today, he is joined by Sullivan Finlay, a comedian and content creator based in Chicago. Sullivan has built a successful following on social media through engaging, humorous, and relatable content. In this episode of "That Worked," Callan and Sullivan dive into topics ranging from emerging health…
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Katie Trauth Taylor - Co-Founder & CEO at Narratize AI: AI-Driven Storytelling, Scaling Innovation, and Creating Serendipity
44:39
44:39
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44:39Katie Trauth Taylor is the CEO and Co-Founder of Narratize AI, a Generative AI storytelling platform for innovative enterprises. Before Narratize AI, Katie received her PhD in Rhetoric and Composition. During her PhD program, she launched her first startup, Untold Content. She is also the host of the Untold Stories of Innovation podcast. In this ep…
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Jane Mosbacher Morris - Founder and CEO of TO THE MARKET: Change Management, Using Capitalism to Make an Impact, and Thought Leadership
36:09
36:09
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36:09Jane Mosbacher Morris is the CEO of To The Market. To The Market is a turn-key solution for ethical manufacturing and sourcing of apparel, accessories, and home goods. Before To The Market, Jane was the Director of Humanitarian Action for the McCain Institute and a Counterterrorism Advisor for the U.S. State Department. She is also the author of Bu…
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Brock Leonti - CEO & Co-Founder of Prescribe FIT: Turning Passion into a Business, Solving Staffing Challenges, and Managing Stress
28:01
28:01
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28:01Brock Leonti is the CEO & Co-Founder of Prescribe FIT. Prescribe FIT is a full-service remote monitoring and lifestyle health coaching solution designed for orthopedic practices and patients. Prior to Prescribe FIT, Brock was the Founder of Larock Healthcare Academy, which was acquired by Beckfield College, and President & Founder of Time For Help …
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Darrin Murriner - Co-Founder & CEO of Cloverleaf: Rejection, Resilience, and Building a Winning Team
33:53
33:53
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33:53Darrin Murriner is the Co-Founder and CEO of Cloverleaf. Cloverleaf is an identity discovery and team-building tool that uses the most common behavioral assessments to help you discover how to work more effectively as a team or as an individual in a team. Prior to Cloverleaf, Darrin co-founded BabysitEase. He is also the author of Corporate Bravery…
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Tim Metzner - Founder & CEO at Fireroad: Nurturing Your Culture, Retaining Top Talent, and Leaps of Faith
33:08
33:08
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33:08Tim Metzner is the Founder and CEO of Fireroad. Fireroad is a new kind of holding company, borrowing the best from venture studios and private equity models. They bring a balanced approach to managing the risk of early-stage ventures with the predictability of enduringly profitable businesses. Prior to Fireroad, Tim was a Founder of Ocean Accelerat…
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Ryan Eder - Founder & CEO of IncludeHealth: Selling Your Vision, Big Pivots, and Design Thinking
41:49
41:49
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41:49Ryan Eder is the Founder and CEO of IncludeHealth. IncludeHealth is an innovative healthcare technology company focused on delivering virtual physical therapy and patient data collection. Ryan has a deep design background, having previously served clients like Nike and GE. He has also twice won Best in Show at the International Design Excellence Aw…
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Sasha Gainullin - CEO of battleface and Robin Assist: Creating a 24/7 Company, Pivoting the GTM Motion, and Balancing Accountability and Autonomy
35:00
35:00
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35:00Sasha Gainullin is the CEO of battleface and Robin Assist. Battleface is a global company enabling customers and partners to easily select travel insurance products and services that perfectly fit their needs. Robin Assist is a tech-driven emergency travel assistance platform supporting the travel insurance industry. Prior to battleface and Robin A…
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Individual Contributor vs. Leadership, Applying Stand-Up and Improv in Business, and Striking a Balance
37:39
37:39
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37:39In this episode of That Worked, host Callan Harrington and co-host Sullivan Finlay dive into a wide array of topics, from recording strategies and Zoom meeting setups to the evolving roles of being an individual contributor vs. leadership within companies. They discuss the balance between career advancement and personal satisfaction, highlighting A…
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Luke Buchanan - Co-Founder of Redi Health: Recruiting Great Employees, Landing Enterprise Deals, and Challenging Your Ideas
47:00
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47:00Luke Buchanan is the Co-Founder of Redi Health. Redi eliminates the confusion and complexity of the health journey through unparalleled access and support. Prior to founding Redi Health, Luke was the Director of Pharma Account Management at CoverMyMeds. He joined CoverMyMeds before its acquisition by McKesson and helped continue to scale the team p…
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Derek & Jessica Crain - Founders at Mindful Therapy Group: Maintaining Quality, Organic Growth, and Navigating Business and Marriage
36:49
36:49
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36:49Derek and Jessica Crain are the Founders of Mindful Therapy Group and Mindful Support Services. When they first founded Mindful Therapy Group, they had a vision of uniting like-minded mental healthcare specialists to serve with compassion, experience, and a fresh outlook on mental wellness. They now serve more than 1000 independent clinicians and h…
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Personal Branding, Content Creation, Managing Stress, and Building Human Connection
43:23
43:23
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43:23In this episode of That Worked, host Callan Harrington and co-host Sullivan Finlay, a writer, comedian, and content creator, explore the importance of personal branding, consistency in content creation, and the value of in-person interactions. Sullivan shares his journey from accounting to full-time comedian, while Callan provides insights on conte…
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Travis Hedge - Co-founder and CRO of Vouch: Startup Secrets - Conquering Adversity and Mastering Product-Market Fit
32:58
32:58
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32:58Travis is the Co-founder and CRO of Vouch. Vouch is the insurance company for the technology industry. Since 2019, Vouch has underwritten billions in risk on behalf of over 4,000 clients, backed by A-rated reinsurers and $165M from Ribbit, YC, Redpoint, and others. Previously, he helped Nationwide Insurance launch Nationwide Ventures before joining…
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Justin Ihnken - CEO & Co-Founder of Enorra_: Overcoming Criticism, Building Networks, and Being Resourceful
44:29
44:29
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44:29Justin Ihnken is the Co-Founder and CEO of Enorra_. Enorra_ is revolutionizing finance by developing SaaS tools that eliminate complexity and accelerate data-driven decisions using machine learning and AI. Their mission is to enhance competitiveness in financial trade, focusing on data analytics, marketplace solutions, and ESG banking. Prior to Co-…
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Ali Schwanke - Founder & CEO at Simple Strat: Leveraging YouTube for B2B Growth, Harmonizing Sales and Marketing, and Cutting Through the White Noise of the Marketplace
43:20
43:20
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43:20Ali Schwanke is the Founder and CEO of Simple Strat. Simple Strat is a marketing and sales firm that helps you get more out of HubSpot. From CRM strategy and setup to marketing automation and content creation, their services are tailored to fuel customer acquisition and retention. Simple Strat is also a HubSpot Diamond Solutions Partner and the hos…
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Wil Schroter - Founder & CEO of Startups.com: From Service Business to Product Business, Embracing Opportunities, and Managing Health
47:38
47:38
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47:38Wil Schroter is the founder and CEO of Startups.com, the world's largest startup platform. They help over one million startup companies find customers, funding, mentors, and world-class education. Before founding Startups.com, Wil founded multiple successful startups like Swapalease.com and Fundable.com. He also founded Blue Diesel at the age of 19…
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Andy Jenks - General Partner at Drive Capital: Bootstrapping vs. Raising Capital, Mission-Driven Startups, and the Silicon Valley Journey
37:12
37:12
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37:12Andy Jenks is a General Partner at Drive Capital, a Columbus-based venture capital firm focused on investing in world-class technology companies outside of Silicon Valley. Before Drive, Andy was a 3-time founder at Formation Data Systems, Discovery Mining, and Infinite Research. Both Discovery Mining and Infinite Research were successfully acquired…
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Ayden Syal - Founder & CEO at MOGL: NIL Dynamics, Startup Scaling, and Influencer Impact
41:38
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41:38Ayden Syal is the Co-Founder and CEO of MOGL, a leading athlete influencer marketplace and NIL software provider that streamlines partnerships between brands and athlete influencers. Prior to starting MOGL, Ayden worked at Morgan Stanley, Lexington Partners, and IHS Markit (now S&P Global). Ayden has been named to the Sports Business Journal New Vo…
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Tim Robinson - CEO of AgencyBloc: Private Equity Transformations, Integrating Acquisitions, and Managing a Leadership Team
36:49
36:49
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36:49Tim Robinson is the CEO of AgencyBloc. AgencyBloc is the leading Insurance Industry Growth Platform serving the health, benefits, and senior insurance space. Prior to AgencyBloc, Tim was the COO of WorkWave, COO of FMG Suite, and COO of Cii. All of those companies are private equity portfolio companies. In this episode, you’ll learn: How to conduct…
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Rick Fox - CRO of Brightway: Leading Leaders, Setting Expectations, and Creating a Performance Culture
37:26
37:26
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37:26Rick Fox is the Chief Revenue Officer of Brightway Insurance. Brightway is one of the largest insurance distribution companies in the U.S., with over 300 franchises in 32 states. Prior to joining Brightway, Rick was the Head of Agency Sales at Vertafore, a leading insurance software company, and previously served as the President of Agency Revoluti…
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Will Zell - Co-Founder and Executive Chair of AssetWatch: Charting Entrepreneurial Waters, Designing Your Life, and Shareholder Thinking
40:03
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40:03Will Zell is the co-founder and Executive Chair of AssetWatch, founder of Vessel, and founding partner of the Ohio Angel Collective. Will has been building and investing in companies since 2006, focusing on venture capital and technology startups since 2012. In this episode, you’ll learn: How to design your life How to navigate the entrepreneurial …
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Matt Wyckhouse - Founder & CEO of Finite State: Building Resilience, Stripping Away Ego, and Cultivating a Feedback-Rich Culture
37:20
37:20
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37:20Matt Wyckhouse is the Founder and CEO of Finite State. Finite State is the leading provider of software risk management solutions for connected devices and software supply chains. Prior to Finite State, Matt was the founder and CTO of Battelle’s Cyber Innovations Business Unit, where he oversaw dozens of intelligence and national security Programs.…
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Grace Nikae - Founder of Kizuna: Career Changes, Zooming Out, and Branding
40:54
40:54
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40:54Grace Nikae is the Founder of Kizuna, a company that helps high-performing startups, subject matter experts, and thought leaders elevate their brand and content strategies across digital platforms. Before founding Kizuna, Grace was an international concert pianist, educator, and fiction author. In this episode, you’ll learn: The power of community …
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Tarek El Gammal-Ortiz - Founder & CEO of Cuddles: Leveling Up, Mastery, and Managing Concentration Risk
42:21
42:21
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42:21Tarek is the Founder and CEO of Cuddles, a cloud-based business management platform that is modernizing the pet industry. Before Cuddles, Tarek was the CEO of HealthySmiles Pet Dental, President of FetchMyVet, and Co-Founder of WashMyWhip. In this episode, you’ll learn: How to create a feedback culture The dangers of concentration risk How to evalu…
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Alex Levin - Co-Founder & CEO of Regal: Accelerating Early SaaS Sales, Transitioning Out of Founder Sales, and Hiring Your First Sales Leader
49:14
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49:14Alex Levin is the Co-Founder and CEO of Regal, a leading cloud contact center specializing in customer engagement. Having secured $42M in funding from Emergence Capital, Regal has attracted over 200 high-consideration consumer services and product companies, including AAA, Angie's List, and SoFi. Before Regal, Alex was the SVP of Growth at Handy, w…
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Greg Kallman - Founder of FanAmp: Influencer Marketing, Community Building, and Idea Validation
47:38
47:38
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47:38Greg Kallman is the Founder of FanAmp, the community hub for all things Formula 1. FanAmp connects fans around the world with each other and their favorite motorsport creators, track guides, and daily news. Before launching FanAmp, Greg spent 12 years advising C-Suite executives and cross-functional teams in the US, Europe, and Asia at Boston Consu…
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