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That Worked

Callan Harrington

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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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Travis 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 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 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 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 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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Matthew 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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Ayden 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 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 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 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 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 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 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 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 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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Alex Harris is the co-founder of Fiat Growth, the Fintech market’s leading growth consultancy, and the co-founder and general partner of Fiat Ventures. Prior to founding Fiat Growth, Alex led Paid Growth and Partnerships at Chime, leading them from Series A to becoming a Unicorn at Series D. Chime is the largest neobank in the US with nearly 20M+ m…
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Taylor Crane is the Founder of Fractional Jobs. Fractional Jobs is the job board for startups to reach and recruit fractional talent. These are part-time leaders embedded into startups to help them scale Before Fractional Jobs, Taylor founded Clubs Poker, which he started in 2020 and sold in 2023. In this episode, you’ll learn: How to turn a proble…
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Paul Monasterio is the CEO and Co-Founder of Kalepa. Kalepa's AI-powered Copilot workbench empowers underwriters to write more profitable business faster. Kalepa was recognized as one of the most innovative insurtechs in the world as part of FinTech Global’s Insurtech 100 in 2022 and 2023. Before founding Kalepa, Paul was an executive at Facebook, …
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Alex Frommeyer is the co-founder and CEO of Beam Benefits, a digitally-led employee benefits company that offers dental, vision, life, disability, and supplemental health coverage. The company simplifies and modernizes the $100+ billion ancillary benefits industry through its intuitive online platform, self-service tools, AI-powered underwriting, a…
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Sam Rose is the Founder and CEO of Mvnifest, a full-stack product agency and 3PL. Before Mvnifest, Sam founded the award-winning kitchenware brand GIR, which she led as CEO until its acquisition by Pattern Brands in 2021. In this episode, you’ll learn: The power of storytelling The Best Day Ever Problem What a boundaryless life looks like How to wo…
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Joe Emison is the Co-Founder and CTO of Branch Insurance. Branch is an insurance carrier that makes it simple to bundle home and auto insurance. Branch was listed on GlassDoor’s Best Places to Work in 2022 and 2023. Before Branch, Joe founded BuildFax (acquired by Verisk), Spaceful (acquired by DMGT), and BluePrince (acquired by Harris Computer). J…
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Omid Bakhshandeh is the Co-Founder of Verneek. Verneek’s mission is to build the most helpful AI, enabling anyone to interact with any environment using intelligent conversational interfaces with deep domain expertise. Omid has two decades of experience in the research and development of AI systems, having founded and successfully led various AI te…
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Sam Jacobs is the Founder and CEO of Pavilion, the essential community-powered learning platform for CEOs, GTM leaders, and their teams. Today, over 10,000 people are paid subscribers to the Pavilion community. Before Pavilion, Sam spent 15 years as a senior revenue leader at VC-backed companies in the New York area, including Gerson Lehrman Group,…
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Jason Molnar is the Co-Founder and Chief Strategy Officer of Infinity Labs. Infinity Labs is a technology company that delivers innovative solutions in various domains. Jason is a decorated U.S. Army combat veteran. He serves on the board of directors of Operation Socrates, a non-profit organization that supports veterans and their families, and on…
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Robin Dimond is the Founder and CEO of Fifth & Cor. Fifth & Cor is at the intersection of strategy, innovation, and creativity. They’re an Innovation and Immersive Marketing company harnessing the best tools to support brands, consumers, and communities. Robin brings over 18 years of marketing experience. She also aspires to uplift communities by s…
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Dan 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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Rachel is the Founder & CEO of Geosite. Geosite is a Y Combinator-backed start-up working to build the geospatial marketplace. Their platform sources, visualizes, and analyzes the relevant geospatial data so their customers can make informed business decisions. Rachel is also completing her Ph.D. in Mechanical Engineering at Stanford and was listed…
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Amy Volas is the Founder and CEO of Avenue Talent Partners, where they help grow early-stage startups through some of their most valuable assets, executive revenue leaders. Amy is a titan in the sales community. She's sold more than 100 million in revenue throughout her sales career. She's a LinkedIn insider and top sales voice, founder, strategic …
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Travis 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…
  continue reading
 
Devin Bostick is the founder and former CEO of LuckyTruck. LuckyTruck makes commercial insurance easy for trucking companies to buy and manage commercial trucking insurance through an all-in-one digital platform. Devin is also an active pre-seed investor through his investment fund, Paracosm Ventures, and teaches entrepreneurial design at the Unive…
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Lissy Alden is the Founder of MYNDY, a research-based mental fitness platform that offers a practical approach to mental fitness which is simple, self-directed, and focused on helping professionals get unstuck, make progress, and feel more focused and energized - daily. Before building MYNDY, Lissy partnered with some of the world’s largest corpora…
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Matt 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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Suresh Rachuri is the Founder of Maven. Maven is an IT Solutions and Consulting business based in Columbus, Ohio. Maven has been solving business challenges through technology and people since 2010. Suresh immigrated from India to Columbus, Ohio, at the age of 4 with his parents and younger brother. Suresh is an avid community leader and has spent …
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Joe Apgar is the President 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 202…
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Mary Wiegand is the CEO and Founder of Boon LLC. Founded in 2017 and run by women, Boon LLC is a hands-on demand planning consultancy. They believe all product-based businesses, regardless of size, deserve access to exceptional merchandise planners. Mary brings over 16 years of demand planning experience across many retail product types and selling…
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Nick Sadler is the CEO of DOmedia. DOmedia is the out-of-home advertising industry’s largest marketplace platform for planning, buying, and selling media. The world’s leading ad agencies and media companies rely on DOmedia’s enterprise solutions, while small businesses use http://www.BillboardsIn.com to plan and execute OOH campaigns online. Before…
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Jill Koziol is the Co-Founder and CEO of Motherly. Motherly is a wellbeing destination empowering mothers to thrive. An Inc. 5000 Fastest Growing Private Company and a Parity.org Best Company for Women to Advance, Motherly is built for mothers, by mothers. Engaging an audience of 40 million+ readers and viewers a month, Motherly offers on-demand pa…
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Ryan is the Founder and CEO of SHARE Mobility. SHARE Mobility empowers businesses, municipalities, and mobility organizations with software and solutions that equip workforces and communities with reliable transportation options. Ryan is a two-time founder. Before starting SHARE Mobility, he founded ContentVia to help tech startups with all things …
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Julia Regan is the Co-Founder and CEO of RxLightning. RxLightning digitizes, automates, and streamlines the historically manual specialty medication onboarding process. Julia has over 15 years of experience delivering innovative healthcare solutions that disrupt the status quo and remove friction for patients, providers, payers, and pharmaceutical …
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Jeff Graley is the Co-Founder and President of Mile 2. Mile 2 builds custom software for a range of diverse clients, including startups, Fortune 500 companies, and the US government. Jeff is a veteran and serial entrepreneur. His 13 years with the Air Force reinforced his strengths as a problem solver and communicator, allowing him to turn existing…
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Sarah Sylvester is the EVP of Marketing at Victoria’s Secret and PINK. She is responsible for telling the product and brand story to customers through all marketing channels, including social, app, email, campus events, direct mail, and in-store activations. Sarah has a tenured career with the company that began in 2005 when she joined Victoria’s S…
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Luis Estevez is the founder and CEO of Advanced & Innovative Multifunctional Materials (AIMM). AIMM enables porous materials to be scientifically tailored to target big problems. More specifically, AIMM focuses on a water filter that can target and treat hard-to-remove “forever chemicals” from water. Before founding AIMM, Luis completed his Materia…
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Nathalie Lussier is the founder of AccessAlly. AccessAlly is a digital course and membership solution for industry leaders. Nathalie believes that access to education can help defy stereotypes and make the world a better place while providing a sustainable livelihood for enterprising teachers. Nathalie is an award-winning entrepreneur who has been …
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Nick Ripplinger is the Founder and President of Battle Sight Technologies. Incorporating his role as a former US Army Soldier and Operations NCOIC, Nick created Battle Sight to protect the warfighter by developing new technologies and innovative ideas. Nick is also the best-selling author of Front Line Leadership – Applying Military Strategies to E…
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Amanda 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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Tom Bruce is the Founder and CEO of Conversion Path. Conversion Path provides e-commerce brands competitive advantages in remarketing, Google Shopping, and paid search engine optimization. Tom started his career as a CPA and CFO for early-stage ventures. As a former CFO turned marketer, he saw an opportunity to use his financial background to optim…
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Christine Rogers is the President and COO of Aspireship. Aspireship is a career development platform that helps you launch and grow your career in tech sales, software engineering, customer success, and many more positions. Christine is a seasoned sales and marketing leader specializing in recruiting, hiring, training, and managing high-performing …
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Derrek Seif is the Chief Strategy and Product Officer at VPL. VPL delivers visibility and resiliency to clinical supply chains. Derrek has built, launched, and managed B2B software products throughout the product lifecycle in several industries. He is doing the same for healthcare at VPL, leading the product and engineering teams to build the futur…
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Ali 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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Brett Buchanan is the CEO of Pathfinder Product Labs, a team of experienced product leaders on a mission to develop products that create lasting customer and business value. Brett is a product expert. He has extensive experience as a Chief Product Officer, ranging from pre-revenue startups to large enterprises. Through that experience, he’s develop…
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