Maddie 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 topline, bottom line, and share growth for multiple billion-dollar brands and products.In this episode, you’ll learn:How to measure if an innovative idea can become a businessThe value of a customer-centric approach to product developmentThe importance of providing value before asking for a habit change from customersThe “mind and heart” insight framework that drives impactful product developmentHow implementing your product in your own business eliminates potential roadblocksFollow Maddie on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Aaron 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 Robots and Devices at Proctor and Gamble. In this episode, you’ll learn:How to balance building the product with building the business. When it’s necessary to bring in experienced operators into a startup. The importance of understanding the financial impact of your product. How to look beyond titles to match the right team member to the right task.  The importance of finding strategic industry investors when introducing a novel product. Follow Aaron on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 was an early employee of CoverMyMeds, moving up the ranks to ultimately serve as Director of New Product Implementation. She played an integral role in the company’s exponential growth and its eventual sale to McKesson in 2017 for 1.4 billion dollars.She also co-founded the non-profit foundation Go Get the World, which supports and empowers young women in college or early in their careers.In this episode, you’ll learn:How to create a network effect How to build a customer flywheelHow to be your authentic self as CEO The fastest way to learn a new industryHow to maintain quality during extreme growthFollow Amanda on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Genevieve 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 before ultimately launching Realword. In this episode, you’ll learn:How to build your MVP as a non-technical founderHow to transition a B2B business to a B2C businessHow to create a marketing strategy for a zero to one productHow to leverage your network for mentorship/advisory supportThe importance of utilizing AI to meet the consumer’s need for automation Follow Genevieve on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Brian 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 Services, managing energy savings projects that highlighted the critical role of proper facilities management, ultimately inspiring the creation of FMX.In this episode, you’ll learn:How to bring facts to a feelings fightThe benefits of waiting to raise capitalThe benefits of a good capital partner beyond cash How to turn mistakes into confidence-building momentsHow to reduce reliance on paid leads and build an outbound engineFollow Brian on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Lindsay 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.Lindsay recently won the Ernst and Young Entrepreneur of the Year Award for the East Central Region. In this episode, you’ll learn:The importance of filtering new opportunities. How to retain talent through performance recognition. How to navigate the fear of letting go and delegating responsibilities. How to turn challenges in one business into new separate businesses. The impact of external accountability with the Entrepreneur Operating System (EOS). Follow Lindsay on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Chris 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 on “red pill or blue pill” momentsThe strategic value of combining software with service The importance of identifying the right data points in human resourcesHow to adjust from large corporate budgets to scrappy start-up marginsHow to identify and sync up with philosophically aligned channel partnersFollow Chris on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Tsavo 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: How to balance gut instinct with market feedbackThe importance of elevating your EQ to put together top-tier teamsHow to reach developers in the sales process through building communityHow to transform organic adoption and early champions into massive growthThe strategy behind company events and engaging the local community to build a positive company cultureFollow Tsavo on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Callan 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 healthcare models to the future of local news, technology, and how both guests are leveraging strategic thinking for growth.In this episode, you’ll learn:A new comprehensive healthcare model. The opportunities for local news to modernize. How to optimize delegating to meet your 10x goals. How to forecast revenue of video content through brand deals. The impact of outsourcing core business functions for large vs small businessesFollow Sullivan on TikTokFollow Callan on LinkedInSubscribe to the Newsletter 

Katie 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 episode, you’ll learn: How to capitalize on referrals to outpace competitors. The most impactful incentives for brand ambassadors. How to build a connected network through hosting think tanks. How to identify and target the right investors as a woman in AI. Where AI is headed to help users learn and grow from tacit knowledge within their enterprise. Follow Katie on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter

Jane 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 Buy The Change You Want to See, a book that explores how you can have a greater social impact through your everyday purchases.In this episode, you’ll learn: How to land clients through customer discovery work. How to address the hesitancy around the cost of change. The importance of buy-in when facilitating change management. How to educate and convince investors on the current state of the market. The benefits of developing a thought leadership reputation for accelerating growth. Follow Jane on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Brock 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 Home Care. In this episode, you’ll learn: The importance of using your PTO. A solution to industry-wide staffing shortages. How to identify when a passion can become a business. How to maintain long-term momentum in a hyper-growth stage. How to finesse your business model to be a “need to have” instead of a “nice to have.” Follow Brock on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter

Darrin 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, a book about eliminating fear-based decision-making and transforming corporate cultures into brave places for people to do their best work and stay engaged. In this episode, you’ll learn: When to leave your corporate job. How to build a balanced leadership team. How to handle rejection from potential funders. How to evolve your role as Founder/CEO as the company grows. The importance of focusing on the end-user experience of your product.  Follow Darrin  on LinkedInFollow Callan on LinkedInSubscribe to the Newsletter 

Tim 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 Accelerator, Differential, and Coterie Insurance. He’s also an active angel investor in 56 deals. In this episode, you’ll learn:How to nurture a great cultureHow to vet a co-founder you don’t knowWhen it makes sense to raise venture capitalThe importance of culture in retaining top talent.The role of early mentorship and unconventional career paths.Follow Tim on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter

Ryan 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 Awards.In this episode, you’ll learn:How to sell your visionA different way of looking at pivotsThe importance of winning strategic awardsThe role of design thinking in solving complex business problems.The challenges and solutions in transitioning from hardware to software in healthcare.Follow Ryan on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Sasha 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 Assist, Sasha was the Interim CEO of Tangiers Group and, before that, the COO of Tangiers International. In this episode, you’ll learn:How to create a 24/7 companyHow to successfully pivot GTM modelsHow to balance accountability and autonomyThe power of immersing yourself in an industryThe importance of being adaptable and responsive in crisis situationsFollow Sasha on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

In 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 Apple's approach to rewarding individual contributors without forcing them into leadership roles. The conversation also covers the benefits of stand-up and improv for personal and professional development, as well as the challenges of navigating social interactions.  In this episode, Callan and Sullivan Discuss:The impact of AI and technology on personal health and productivity.How to reward individual contributors that don't want to go into management. The creative process behind Sullivan's content and how he keeps it engaging.The importance of personal and professional balance in achieving long-term success.Insights into the challenges and rewards of pursuing a career in comedy and content creation.Follow Sullivan Finlay on TikTok and InstagramFollow Callan on LinkedInSubscribe to the Newsletter 

Luke 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 post-acquisition. In this episode, you’ll learn:How to Operate with 4 Co-FoundersHow to Recruit Great Early EmployeesHow to Find Your First Enterprise ClientsThe Mindset Needed to Win Enterprise DealsHow to Balance Working on the Core Business vs. What Comes NextFollow Luke on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Derek 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 have collectively served over 48,000 families, couples, teenagers, and children seeking to improve their lives with professional guidance.In this episode, you’ll learn:How to maintain quality while scaling Strategies for scaling a business organicallyThe importance of healthy boundaries in businessThe benefits of having a visionary and an operator as partnersHow to balance marriage and business partnership successfullyFollow Derek on LinkedInFollow Jessica on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

In 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 content strategy and founder experiences. They discuss strategic goal planning, the significance of human connections, managing stress, and adapting to new opportunities, offering valuable perspectives on achieving personal and professional growth. In this episode, you’ll learn:Strategies for maintaining consistency and creativity.How to leverage social media to build a personal brand.Insights into managing stress and maintaining a work-life balance.The transition from a corporate career to full-time content creation.The importance of human connection in personal and professional growth.Follow Sullivan Finlay on TikTok and InstagramFollow Callan on LinkedInSubscribe to the Newsletter 

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 Silicon Valley Bank’s Venture Capital group, where he raised over $1B from institutional investors to invest in fintech and digital health startups, including Root Insurance, Ladder Life, and Earnin. In this episode, you’ll learn:How to respond to adversity What makes a good co-founderHow to host a small group dinner The importance of geographic location How to leverage community-led growth Follow Travis on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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-Founding Enorra_, Justin Co-Founded QNTM Labs, a contract laboratory focused on providing chemical and biological analysis, as well as contract research, development, and regulatory compliance applications to pharmaceutical companies.In this episode, you’ll learn:The importance of resourcefulness in a startupHow to get up to speed on a new industry quicklyHow to effectively transition from one industry to anotherThe benefits of hiring senior talent early to accelerate business growthThe significance of pushing through criticism and rejection in entrepreneurshipFollow Justin Ihnken on LinkedInFollow Callan on LinkedInSubscribe to the Newsletter 

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 host of HubSpot Hacks, the #1 unofficial YouTube channel for HubSpot Tutorials.Ali is a data-driven marketing professional with 15+ years of experience in B2B, strategy, and content marketing. Most of all, she’s hilarious.In this episode, you’ll learn:What makes a good first hireHow to align sales and marketing teamsHow to build a YouTube channel for B2BThe benefits of a peer network as an entrepreneurHow to differentiate yourself in a competitive marketFollow Ali on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 and grew it to $700 million in capitalized billings before it became inVentiv, now valued at $6 billion dollars. In this episode, you’ll learn:The impact of extreme stress on founders How saying "yes" to opportunities can open unexpected doors.The significance of having a mission-driven approach in business.The transition from a service-based business model to a product-based one.The importance of balancing multiple ventures and managing personal life effectively. Follow Wil Schroter on LinkedInFollow Callan on LinkedInSubscribe to the Newsletter 

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. In this episode, you’ll learn:Experiences from the early days of Silicon Valley.When to take venture capital instead of bootstrap. The critical role of being mission-driven in a startup.When to bootstrap instead of taking venture capital. The importance of understanding your fit within the business stages.Follow Andy on LinkedInFollow Callan on LinkedInSubscribe to the Newsletter 

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:The importance of establishing a company's DNA and core values earlyThe value of having a complementary and trustworthy business partnerHow to increase your employee retention rate in a high attrition businessStrategies for leveraging small communities to build a successful businessHow taking chances and learning new things can help you find your calling Follow Matthew on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 Voices Under 30 list, The Marquis "Who's Who in America" list, and won the 2022 SXSW Pitch competition on behalf of MOGL.In this episode, you’ll learn:Tactics for fundraising A playbook to distribute thought leadershipHow to get traction in marketplace business How to leverage influencers to grow your businessInsights into the Name, Image, and Likeness (NIL) industryListen to Ayden's SXSW Talk & follow Ayden on LinkedInConnect Callan on LinkedInSubscribe to the Newsletter

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 a daily leadership team huddle The lifecycle of a private equity portfolio company How to manage and integrate company acquisitions How private equity investment impacts business operations.The journey from VP to Chief Operating Officer in a private equity environment.ConnectFollow Tim Robinson on LinkedIn ConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 Revolution, an agency automation and marketing consultancy.In this episode, you’ll learn:How sports principles can transform corporate leadershipStrategies for building resilience and adaptability in teamsThe importance of setting clear expectations for team successTechniques for fostering a feedback-rich culture in any organizationThe significance of discipline and commitment in achieving personal and professional goalsFollow Rick Fox on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 lifeHow to navigate the entrepreneurial journey The role of a long-term vision and strategic pivotsWhy it’s important to think of yourself as a shareholder first Insights into creating a business ecosystem that fosters community and fulfillment.References:The Creative Act: A Way of Being by Rick RubinThe Ohio Angel CollectiveVessel Venture Capital CompanyConnect Follow Will Zell on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 InnovationsBusiness Unit, where he oversaw dozens of intelligence and national securityPrograms. In this episode, you’ll learn:How to keep your ego in balance The benefits of an executive coach How to build resilience as a founder How to know when to hire an employee How to build a culture based on feedbackFollow Matt on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 How to build brand advocates How to approach a career change When to zoom in and when to zoom outThe importance of letting creative work breathe Follow Grace on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 riskHow to evaluate a potential market How great people force you to be betterThe benefits of working towards mastery Follow Tarek on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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, where he was an early employee and grew with the company through their acquisition by the publicly traded company Angi. In this episode, you’ll learn:When to hire the first sales leaderHow to accelerate SaaS sales early onHow to think about deploying venture capital The power of tracking where you’re spending your timeWhen to transition from founder sales to professional salesFollow Alex on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 Consulting Group (BCG) and J.P. Morgan. In this episode, you’ll learn:The benefits of unscalable activities How to leverage influencer marketing The power of visiting your clients in personHow to objectively validate your product ideasThe importance of focusing on your Ideal Customer Profile Follow Greg on LinkedInDownload the FanAmp AppConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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+ members and was most recently valued at $25B.In this episode, you’ll learn:How to nurture a partnership When to add your next offering How to maximize a partnership How to test if a Co-Founder is the right fitHow to evaluate when to make major business movesFollow Alex on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 scaleBefore 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 problem into a business The pros and cons of taking Venture CapitalHow to cost-effectively grow through acquisition How taking on investment impacts your business The difference between bootstrapping and taking on investment Follow Taylor on LinkedInLearn more about Fractional JobsConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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, Mastercard, and Applied Predictive Technologies. Paul also graduated with a PhD in Nuclear Science and Engineering at MIT. In this episode, you’ll learn:What to look for in a Co-FounderThe importance of finding the right first customerThe benefits of having sales experience as a founderThe importance of full transparency in every interview The value of working for a startup before starting a company Follow Paul on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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, and thoughtful coverage for improved overall wellness. Beam has raised over $200 million in funding and is available in 44 states across the U.S. Learn more at beambenefits.com.In this episode, you’ll learn:How to maximize a 360 reviewHow to create a feedback culture The difference between a Founder and a CEOHow to use services revenue to fund your startup The challenges and opportunities of being a Midwest startup Follow Alex on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter

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 likeHow to work with friends and family The benefits of working at an early-stage company Follow Sam on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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). Joe is also an author and released his new book "Serverless as a Game Changer: How to Get the Most out of the Cloud"In this episode, you’ll learn:How to identify your strengthsHow to create a bootcamp to hire better people The benefits of being “agile” and going serverlessA strategy that allows you to hire junior developers How to maintain the culture as the company scalesFollow Joe on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 teams. He received his Ph.D. in AI with a focus on Natural Language Understanding and Dialogue Systems and is a published author in multiple major AI publications.In this episode, you’ll learn:How to evaluate an AI companyThe benefits of an advisory board Where AI is not replacing humansThe challenges of the current AI market How to raise capital without an established network Follow Omid on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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, Axial, Livestream/Vimeo, The Muse, and Behavox.In this episode, you’ll learn:How to manage hypergrowthThe importance of recognitionHow to take control of your life The benefits of leading from the front What needs to change as the business growsFollow Sam on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 the board of directors for the Ohio Veterans Collaborative, whose mission is to help Ohio Veterans find success outside of the uniform.In this episode, you’ll learn:How to deploy “sales by saturation” The benefits of a large founding teamThe importance of geographic locationHow to drive early sales in a new company How to setup your business to foster innovation Follow Jason on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 sitting on multiple school boards and actively participating in various charitable initiatives. In this episode, you’ll learn:How to put on an event How to build your culture The importance of experienceThe power of having a “battle buddy”How to build and nurture strategic partnersFollow Robin on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 technology-powered car insurance carrier, which he co-founded in 2015 and took public via an IPO in 2020. Before Root, Dan was the CTO of Braintree, where he built a payments platform that PayPal acquired in 2013 for $800M.In this episode, you’ll learn:The unique challenges engineers face What to look for in a technical co-founderWhat to look for in a non-technical co-founder  The benefits of assigning a mentor to new employees Why you need to focus on the problems you’re having now Follow Dan on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 on the Forbes Top 30 under 30 list. In this episode, you’ll learn:How to prototype your lifeHow to find your strengths The pros and cons of being a solo founderWhy you need to be obsessed with the problem How to sell new tech to large bureaucratic organizationsFollow Rachel on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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 advisor, and LP at Stage 2 Capital. In this episode, you’ll learn:The power of self-belief What bad recruiting looks likeHow to evaluate your next position How to build your ideal candidate profile Why you need to be crystal clear about what you’re looking forFollow Amy on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter