The Insurance Growth Lab

Callan Harrington sits down with Lyndon Block, President & CEO of Block's Agencies, Prairie Insurance, Mello Insurance, and Rosthern Agencies, to explore his unconventional path to building 7 insurance brokerages across Saskatchewan. Lyndon shares how a chance encounter with marketing expert Chris Paradiso at a conference sparked a relentless pursuit of digital marketing mastery that changed everything. After being called out for doing "nothing" with his marketing efforts, Lyndon's persistence led to a life-changing mentorship in Connecticut, where he learned the fundamentals of digital growth.The conversation reveals Lyndon's dual strategy of building both a self-funded digital insurance platform and acquiring struggling small-town agencies. He explains why distressed assets in rural communities represent hidden opportunities and how his boots-on-the-ground approach builds the trust necessary to turn around declining agencies.This episode offers practical insights for anyone looking to grow through acquisition or build authentic community connections in their business.Key topics covered:[00:00] Intro[02:09] Wake up call from insurance marketing guru[03:32] Flying to Connecticut for free training[05:55] Persistence as a competitive advantage[08:00] Self funding a digital insurance agency[09:27] Gary Vaynerchuk's cannibalization strategy[11:19] Building API bridges for online insurance[12:02] Old school door knocking for lead generation[14:17] Two minute tenant insurance buying process[16:37] Small town community strategy explained[18:58] Why buy struggling insurance agencies[21:33] Small town loyalty creates sticky clients[25:02] Turning around distressed agencies[28:40] Being present at hockey games and pancake breakfasts[31:17] Using comedy to generate insurance business[34:44] Digital versus community agencies coexisting[36:56] Never say no to opportunitiesConnect with Lyndon Block on LinkedIn: https://www.linkedin.com/in/lyndonblock/Subscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

Curtis Barton didn't take the traditional path to building a large platform agency. He convinced six agency owners to merge their businesses, raise private equity capital together, and build something that had never been done in the industry. ALKEME is now ranked 21st on the Insurance Journal top 100, with over $2 billion in premiums written, $122 million in EBITDA, and 83 acquisitions completed.Callan Harrington sits down with Curtis to break down how ALKEME was built from the ground up, why they moved every agency onto a single integrated system before anyone was talking about it, and how they use AI today to turn account managers from reactive paper pushers into proactive mini-salespeople. This episode is a blueprint for any agency owner thinking about what it actually takes to scale past a lifestyle business and build something that lasts.Key topics covered:[00:00] Intro[01:18] Skiing teaches business adaptation skills[04:24] Why leaders must explain change[06:48] Building agency from zero revenue[09:02] Lifestyle business versus generational wealth[11:00] Constant reinvestment beats traditional playbooks[12:36] Eight agencies merge into platform[17:19] Roadblocks to starting agency platforms[22:23] Pick niche then hyper niche[25:18] Organic growth fuels acquisition capacity[28:58] AI automates workflow from inbox[32:16] Blind scoring acquisition targets[36:22] Scale beats growth every time[40:07] Maturity means leading with intelligence[44:49] Building forever company not exitConnect with Curtis Barton on LinkedIn: https://www.linkedin.com/in/curtisbartonSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

Callan Harrington sits down with Andy Cohen, President and COO of Snapsheet, to dive into why claims operations represent the biggest opportunity left in insurance, and what it actually looks like when carriers get it right. Andy brings perspective from both the carrier side and Snapsheet's work with over 180 carriers, including 16 of the top 20 P&C carriers. Andy covers why loss adjustment expenses have barely moved even as premiums have surged, what modern claims operations actually look like when they're working, and what brokers and agents should be asking their carrier partners to hold them accountable on performance.This episode provides actionable insights for anyone looking to understand how claims technology can drive better outcomes and competitive advantage in today's insurance market.Key topics covered:[00:00] Intro[01:15] Change Management Takes 3 Years at Carriers[03:02] AI Moving Fast in Insurance[06:16] Snapsheet's 180 Carrier Network[08:10] Claims Tech Overnight Success 14 Years Later[10:59] Brokers Haven't Paid Attention to Claims[15:28] Agents Can Vote With Their Feet[18:03] Questions Agents Should Ask Carriers[21:07] Best Practices from Top Carriers[24:08] Key Questions About Loss Adjustment Expense[26:28] Modern Claims Process Breakdown[30:40] Where Agents Insert Themselves[32:49] The Next 10 Years of Claims[36:03] Modernization vs True Transformation[38:31] Claims as Competitive AdvantageConnect with Andy Cohen on LinkedIn: https://www.linkedin.com/in/andrewjustincohenSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

Host Callan Harrington sits down with Paul VanderMarck, Chief Technology and Innovation Officer at SageSure, to explore what the best insurance producers actually do differently, and why a softening market is about to make that question impossible to ignore.Paul shares how top producers navigate the shift from a supply-constrained hard market to one where competition on price is back, and carriers are getting aggressive. He walks through a real example of how an admitted policy with full replacement cost coverage is a fundamentally different product than a surplus lines policy with a roof payment schedule, and why the agents who can explain that difference are also the most insulated from AI reshaping distribution.This episode is a must-listen for any producer or carrier executive trying to understand where distribution is headed and what it actually takes to win in a softening market.Key topics covered:[00:00] Intro[01:09] Mountain bike sales lesson for insurance[04:19] Why insurance isn't really a commodity[06:42] What top producers actually do differently[09:17] True advisory selling versus order taking[12:27] Technology supporting producer education[16:34] Hard market survival strategies for agents[19:39] Soft market competition and pricing tactics[22:55] AI deployment in insurance operations[25:28] AI threat to insurance distribution channels[28:37] Future of AI in customer acquisition[31:26] Leveraging AI for producer training acceleration[35:27] Insurance as life partnership visionConnect with Paul VanderMarck on LinkedIn: https://www.linkedin.com/in/pvandermarckSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

Host Callan Harrington sits down with Kyle Nakatsuji, CEO and Founder of Clearcover and Dearborn Labs, to explore how AI is reshaping insurance from the ground up. Kyle shares his unconventional path from persistent business school dropout to insurance entrepreneur who raised over $500 million and built technology capable of processing claims in 7 minutes.The conversation dives into Kyle's decision to launch Dearborn Labs, essentially bringing a decade of hard-won AI deployment lessons to carriers and agencies who can't afford to wait. Kyle explains why the recent leap in reasoning capabilities from frontier models like Claude Opus 4.6 represents a genuine inflection point, not just incremental progress. He outlines a future where agents interact with AI orchestrators rather than navigating fifteen carrier portals, with context rather than software becoming the true competitive currency in insurance.Kyle's insights on the K-shaped economy emerging from AI adoption offer a clear roadmap for insurance professionals ready to embrace the technology revolution transforming their industry.Key topics covered:[00:00] Intro[03:42] Business school persistence pays off[06:13] Competing against billion dollar ad spends[07:07] Seven minute claim payout achievement[08:15] Why launch Dearborn Labs now[10:27] AI breakthrough moment arrives[12:23] Agent experience transformation begins[15:11] API for AI agents explained[20:11] Who builds the connection layer[24:18] K shaped AI adoption reality[28:34] Start simple with AI tools[31:06] Technology curve never flattens[32:18] Discovery process for carriers[35:58] Building hammers versus finding nails[37:17] Advice to younger selfConnect with Kyle Nakatsuji on LinkedIn: https://www.linkedin.com/in/kylenakatsujiSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

Matt Naimoli went from college baseball player to building one of the fastest-growing insurance agencies in America using an unconventional $10,000 bobblehead campaign. What started as a networking attempt became a systematic referral machine generating 500 warm leads monthly with a 75% closing ratio.In this episode, Callan Harrington sits with Matt to break down the exact process behind the campaign that helped his agency capture 7% of all new home sales in Massachusetts. He reveals how they identified centers of influence, created systematic follow-up processes, and built relationships with 100+ referral partners who consistently sent high-quality leads.Matt also shares insights from his current role helping agency owners maximize their business value for acquisition. He explains what buyers actually pay premiums for, why growth matters more than book composition, and how to position your agency in today's market.Whether you're starting an agency or looking to scale, this episode provides a blueprint for building sustainable referral systems that compound over time.Key topics covered:[00:00] Intro[01:17] Baseball to Insurance Career Journey[04:24] Sales Stereotypes vs Reality[06:11] From Liberty Mutual to Agency Success[07:05] The Office Inspired Bobhead Campaign[10:11] Identifying Centers of Influence Strategy[12:08] Building Systematic Networking Processes[16:26] Written Process for Relationship Building[19:47] Modern Bobhead Campaign Revival[23:23] What Drives Agency Valuation Today[27:42] Scale Growth and Leadership Matter Most[32:29] Advice for Next Generation Agency Owners[34:41] How Carriers Can Support Growth[38:39] Long Term Reputation Over ShortcutsConnect with Matt Naimoli on LinkedIn: https://www.linkedin.com/in/mattnaimoliSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

Host Callan Harrington sits down with Jim Waterwash, Partner at INSocial Risk Advisors, to get into the details behind their 90%+ retention rate across 5 agency acquisitions, as well as the hard lessons that got them there.Jim traces the arc from running a fully digital agency selling 100% over the phone, to building a traditional operation with 20+ employees, $20M+ in premium, and a repeatable acquisition playbook. The insight that changed everything: the challenge of retaining a client you've never met is the same whether they came through an online lead or a book of business you just purchased.The conversation gets specific on how they identify cross-sell opportunities (they have actual coverage thresholds), how their pod-based service model works in practice, and why trying to build standard operating procedures collaboratively with acquired teams instead of arriving with them already built is big mistake.This episode offers actionable insights for agency owners considering acquisition strategies or looking to improve retention rates across diverse client bases.Key topics covered:[00:00] Intro[01:05] First Policy Double Charge Disaster[03:54] From Digital Leads to Traditional Agency[05:24] Why Digital Strategy Stopped Working[06:40] Acquisition Retention Similarity Insight[08:50] Great Insurance Minds Foundation[10:10] Book Integration Process Walkthrough[11:14] Change Management and Cultural Buyins[12:11] Cross Selling Acquired Books[14:03] Pod Based Service Model[16:51] Early Acquisition Road Bumps[19:42] Standard Operating Procedures Missing[22:17] Proving Systems Before Implementing[24:44] Craft Brewery Cash Deal[27:09] Cultural Alignment During Courtship[29:59] Carrier Support for Acquisitions[31:37] Keep Going AdviceConnect with Jim Waterwash on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/jwaterwash/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Jeff Snyder, President of Matic, to break down how an “unqualified” first employee built one of the most successful embedded insurance platforms in the mortgage servicing space. Jeff shares the unconventional strategy behind generating 750,000 leads annually by focusing on loan servicing rather than origination, targeting 65 million outstanding mortgages instead of the typical 4 to 6 million new home loans.Jeff walks through the three distinct phases of scaling Matic from an 800 square foot office to over 400 employees and 50 million in funding. He reveals his 3 by 3 relationship grid for partnership management, lessons learned from losing a major partner due to relationship turnover, and why providing value before asking for conversion creates lasting partnerships. The conversation covers everything from making 350 cold calls daily in the early days to building deep integrations with mortgage servicers that prove measurable impact on their core recapture rates.An essential listen for anyone building partnership-driven growth strategies or navigating the challenges of scaling from startup to enterprise.Key topics covered:[00:00] Intro[03:01] Taking Unqualified Opportunities That Change Careers[05:08] Becoming First Employee Twice[07:17] Generating 750,000 Leads Per Year[08:30] Why Loan Servicing Beats Origination[11:32] Triggering Customer Interest Through Data[14:05] Building Revenue Share Partnerships[18:02] Adding Value Without Selling[21:18] Proving Impact on Customer Retention[23:03] Losing a Major Partner[25:05] Building 3x3 Relationship Grids[30:23] Evolving Through 3 Company Stages[32:31] Scrappy Startup Phase Stories[36:37] Scaling Challenges and Bad Hires[38:27] Building Elite Leadership Teams[39:11] What to Stop Doing at Each StageConnect with Jeff Snyder on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/jeffrey-snyder-9189b317/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Eric Roberts, owner of My Insurance Group, to break down the systematic approach behind building a $20 million agency that generates 270 new inbound leads monthly without any cold calling. Eric brings a unique perspective to insurance sales, having spent 15 years on the claims side doing water and fire restoration before transitioning to agency ownership. The conversation dives into Eric's cross-sell engine, which has more than doubled his policies per household. His team operates under a "respectfully aggressive" motto, focusing on thorough discovery during every client interaction to uncover additional insurance needs. Eric explains his unique team structure that separates new business, renewal, and service teams, with each playing a specific role in the cross-sell process. He also shares the tactical systems his agency uses, from their renewal questionnaire process to their CRM tagging system that tracks every opportunity.Eric's systematic approach shows how independent agencies can compete with the efficiency of captive carriers while maintaining their flexibility advantage.Key topics covered:[00:00] Intro[01:16] Career Journey from Claims to Sales[03:03] Understanding Insurance from Claims Perspective[04:33] 270 Monthly Leads Without Cold Calling[05:21] Respectfully Aggressive Agency Philosophy[06:37] Discovery Process for New Prospects[08:28] Standardized Scripts vs Producer Freedom[10:38] Detailed Renewal Journey System[14:50] Unique Team Structure Strategy[17:47] Why Separate Renewal and Sales Teams[20:07] Service Team Cross-Sell Process[22:17] Building Systematic Cross-Sell Culture[27:11] First Step for Starting Cross-Sell[30:16] Path to 50 Million PremiumConnect with Eric Roberts on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/eric-roberts-1b819b5b/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Eddie Knezevich, President & CEO of NLF Partners, to break down the continuing education lead generation system that transformed his wealth management practice. Eddie shares how he built a machine that generates 2000 qualified leads monthly without relying on friends and family networks or traditional cold calling.Eddie walks through his journey from hosting 3-person events in Newark, Ohio to running virtual webinars with 2500 attendees across multiple states. He explains the tactical details of his process-driven approach, from surveying audiences to create relevant content to converting attendees into scheduled consultations. The conversation covers the compliance challenges of expanding across state lines, the infrastructure required to scale continuing education programs, and how Eddie uses this system to feed his team of 12 advisors who manage billions in assets.Eddie emphasizes focusing on what you know and building systems that work without you, sharing lessons learned from 10 years of refining this lead generation approach.Key topics covered:[00:00] Intro[03:42] From Upper Middle Class to Food Stamps[06:09] Building Momentum After Rock Bottom Years[08:29] Factory Model Approach to Financial Services[10:53] First Continuing Education Event Disaster[12:01] Surveying Clients to Create Better Content[16:15] Building Transactional Relationships First[18:43] Marketing Process and Lead Generation Flow[21:27] Compliance Hurdles Across Multiple States[24:56] Marketing Tactics for Million Person Email List[29:57] Multiple Revenue Streams Beyond Ce Events[31:09] Focus on What You Know Best[33:24] Own What You Sell Philosophy[35:42] Starting Over Lessons Learned[37:08] Hiring People Sooner Despite Impostor Syndrome[40:47] Sacrificing Twenties to Build Lead Machine[42:31] Final ThoughtsConnect with Eddie Knezevich on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/eddieknezevich/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Host Callan Harrington sits down with Patrick McBride, founder of The McBride Agency, to explore his unconventional approach to building a successful independent insurance agency. Patrick shares how he transformed his personal passions for motorcycles and cycling into profitable niche markets, targeting high-value clients who own expensive Harley Davidson motorcycles and premium bicycles.Patrick dives into his creative marketing strategy to reach motorcycle enthusiasts and discusses the importance of understanding coverage needs specific to these communities, from accessory upgrades to personal articles floaters. The conversation covers his biggest operational challenges as the agency has grown, including knowledge transfer to new team members and the critical importance of carrier ease of use over pricing.Patrick delivers practical insights on community-based marketing, niche targeting strategies, and the systems needed to scale a scratch-built insurance agency.Key topics covered:[00:00] Intro[01:14] Never Give Clients Your Cell Phone[08:42] Targeting Harley Davidson Owners[12:46] Using Reddit for Customer Acquisition[16:10] Creating Custom Audiences Through Pixelation[18:16] Building Community Through Referrals[20:29] Operationalizing Niche Marketing Strategies[24:35] Launching the Cyclist Community Focus[30:22] Current Agency Growth Challenges[32:42] What Carriers Are Doing Right[35:59] Starting an Agency From ScratchConnect with Patrick McBride on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/patrick-j-mcbride/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Andy Harbut, Co-Founder of NewCo Risk, who built a multi-million dollar insurance brokerage in just one year after leaving the big brokerage world. Andy shares how he and his partner, Josh, carved out their own path, focusing on search fund clients and lower middle-market private equity deals. With 75% of their clients being entrepreneurs who bought their own businesses, Andy explains why this niche offers more personal satisfaction than working as a cog in a large institutional machine.Andy breaks down their growth strategy built on old-school relationship building through conference sponsorships, university events, and face-to-face networking within the search fund community. He discusses the challenges of carrier selection across 40 states, why they wholesale specialty lines to true experts, and how they compete against major brokers by offering intimate client relationships and direct accountability. The conversation covers everything from insurance diligence in M&A transactions to why Andy insists on calling himself a broker rather than an agent.This episode offers tactical insights for any insurance professional looking to understand niche market development and independent brokerage growth strategies.Key topics covered:[00:00] Intro[04:26] Why Start Your Own Brokerage[07:51] Extreme Growth in Search Fund Niche[13:14] Unique Competitive Positioning Advantage[16:01] Old School Selling Insurance Strategy[17:32] University Conference Marketing Approach[20:03] Building Messaging Around Unknown Problems[21:58] National Carrier Selection Challenges[24:06] Program Business Growth Strategy[28:20] Leveraging Underwriting Office Arbitrage[32:46] Wholesaling vs In-House Expertise[36:21] Why Broker Not Agent[39:49] Fee Only Model Exploration[42:54] Growing the TeamConnect with Andy Harbut on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/andyharbut/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Jennie Lyttle, Sales Director at Salt and one of the most skilled cold callers in insurtech. Jennie breaks down her most successful campaign ever, the “broker box” initiative at Beam Benefits that delivered over 300% ROI despite being launched without approval. She explains how she turned leftover Bluetooth toothbrushes from Beam's warehouse into a powerful lead generation tool that forced the company to hire additional sales reps to handle demand.The conversation shifts into a comprehensive look at cold calling in today's insurance market. Jennie shares her current approach for both inbound and outbound prospects, explaining why she sends resource emails before calling inbound leads but starts with calls for outbound. She details her qualification process, emphasizing the importance of determining fit before booking demos, and discusses the growing trend toward full-cycle sales roles versus separate BDR teams.This episode delivers practical insights for anyone running outbound campaigns or looking to improve their cold calling effectiveness in the insurance space.Key topics covered:[00:00] Intro[02:44] Email Campaign Mistake[04:20] Turning Marketing Errors Into Wins[08:23] The Beam Benefits Broker Box Campaign[11:18] 300% ROI From Unsanctioned Campaign[13:20] Cold Calling State of the Union[15:28] Inbound vs Outbound Call Strategies[19:36] First 30 Seconds of Cold Calls[21:35] Qualifying Prospects Over Meeting Setting[23:25] Full Cycle Sales vs BD Teams[26:42] Selling to Insurance Agents Successfully[29:46] Why Insurance Professionals Never Leave[32:27] Early Adopter Agency Relationships[34:17] Starting Over at The Shipyard[36:57] Consistency Beats Talent Every Time[40:27] Self-Reflection in Sales PerformanceConnect with Jennie Lyttle on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/jenlyttleSubscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Clinton Houck, VP of Insurance and Distribution at Fair, to explore how to successfully drive adoption of non-core products within P&C insurance agencies. Clinton brings serious insurance experience from every angle, having worked as an underwriter at State Farm, owned his own agency, and held leadership roles at multiple insurtech companies.Clinton reveals Fair's systematic approach to breaking through the traditional home, auto, and umbrella offering stack that most P&C agencies stick to. He shares how they achieved a 12% attachment rate by positioning auto warranty not as a separate product sale, but as a natural extension of the auto insurance conversation. The key insight is treating warranty like an endorsement rather than forcing producers to learn an entirely new sales process, making it feel complementary to existing coverage discussions rather than disruptive.This episode delivers tactical frameworks for anyone looking to distribute ancillary products through insurance agencies, from winning over principals to ensuring producer adoption through superior user experience and comprehensive training programs.Key topics covered:[00:00] Intro[02:28] First insurance industry rude awakening[06:22] Sitting in every seat drives career decisions[09:40] Breaking through P&C agency core offerings[12:07] Money talks but ease of use wins[17:25] Progressive's user experience advantage[20:00] Auto warranty fits naturally with insurance[22:21] Winning principals vs producers[26:13] Higher commissions than traditional P&C[29:25] Digital vs main street agency differences[32:43] Speed vs advisory value propositions[36:31] Where most ancillary products fail[39:38] Simplifying coverage options backfired[41:39] Claims transparency builds trust[43:17] Cold calling agencies doesn't workConnect with Clinton Houck on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/clinton-houckSubscribe for more insurance growth strategies and connect with Callan Harrington on LinkedIn for additional insights.

Callan Harrington sits down with Caleb Cramer, Chief Revenue Officer at LAUNCH, to break down the exact group demo process that helped AgencyZoom onboard thousands of agencies to their CRM product. Caleb shares his experience working across insurtech, agency networks, and service businesses, explaining why he believes the insurance industry attracts people who want to help others despite lacking the technology tools other verticals take for granted.The conversation dives into the tactical details of running effective webinars versus one-to-one sales calls. Caleb walks through his complete process from cold calling with validated problem statements to nurturing prospects through text messaging and structured webinar experiences. This episode provides actionable insights for any insurtech company looking to maximize their sales resources while building trust through group experiences rather than traditional individual demos.Key topics covered:[00:00] Intro[03:02] Why Insurance Industry Attracts Tech Talent[05:47] Differentiation Challenges Facing Producers[08:03] Dale Carnegie Problem in Sales Discovery[11:00] Group Webinars vs One to One Demos[13:13] Problem Statement Validation Through Customer Interviews[16:08] Segmentation Process for Targeting Agencies[19:50] Cold Call Structure with Problem Hypothesis[21:00] Moving Prospects to Text Communication[25:47] Rep Ownership vs Marketing Sequences[28:46] Group Demo Content Structure[30:14] Making Prospects the Hero Not Victim[34:22] Curated Product Moments Over Full Tours[36:15] Post Demo Follow Up Strategy[40:21] When Group Demos Don't Work[43:48] Scaling Lessons from Agency ZoomConnect with Caleb Cramer on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/caleb-cramerSubscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington sits down with Brad Barnett, former VP of Enterprise Marketing at Nationwide and current independent consultant, to break down one of insurance marketing's most successful campaigns. Brad managed over $300 million in annual media spend and a $50 million portfolio of sports and entertainment partnerships during his 20-year tenure at Nationwide. He was instrumental in developing the iconic NFL partnership featuring Peyton Manning and the return of the famous "Nationwide is on your side" jingle that became a cultural phenomenon.Brad shares the strategic thinking behind Nationwide's entry into NFL sponsorship, from competing against Geico and Progressive's massive advertising budgets to creating unique B2B experiences for distribution partners. He reveals how the campaign achieved the highest brand awareness scores in Nationwide's 100-year history and explains the behind-the-scenes process of talent selection, Q-score analysis, and managing reputation challenges. The conversation covers everything from negotiating category sponsorships to measuring ROI on major sports partnerships.Key topics covered:[00:00] Intro[03:04] Crowd Pleasers and Karaoke Strategy[06:37] Product Experience Drives Marketing Success[09:52] Nationwide Career Path to CMO[12:52] NFL Partnership Origins and Strategy[16:55] Official NFL Sponsorship Benefits[19:09] Peyton Manning Selection Process[21:22] Bringing Back the Jingle[25:29] Strategic Bet and Executive Buy-in[28:21] Distribution Partner Experiences[34:24] Brand Awareness vs Direct Consumer[36:31] Managing Reputation Challenges[39:40] Entrepreneurial Leap Decision[41:12] Outworking Competition Early Career[42:14] Natural Curiosity as Differentiator[43:18] Intentional Relationship BuildingConnect with Brad Barnett on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/bradbarnett05/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Host Callan Harrington breaks down why the insurance industry may be entering a new growth phase and shares a standout story from his Bold Penguin days that proves what’s possible when momentum shifts. With enterprise carrier spend up 27% and major players like Nationwide committing $1.5 billion to tech, all signs point to a market ready to get back on offense.In this episode, Callan unpacks what it really takes to capitalize on that kind of opportunity. He explains how the Bold Penguin team hit a nearly impossible sales goal during what most consider to be the “slowest” month of the year by throwing out their usual processes and going all-hands-on-deck. What started as chaos turned into one of the most successful campaigns of his career, teaching him that sometimes you need to do things that don't scale to capture major opportunities.Key topics covered:[00:00] Intro[01:20] Growth Period Signs Emerging[02:34] EverQuote Earnings Signal Carrier Spending[03:22] Nationwide's $1.5 Billion Tech Investment[04:02] Window of Aggressive Growth Opportunity[06:09] Bold Penguin's 200 Agency Challenge[07:28] Setting Stretch Goals vs Impossible Goals[08:30] Commercial Rating Platform Background[10:48] November December Sales Reality[11:24] All Hands Blitz Strategy[12:52] Team Rally Around Shared Goal[14:46] Hitting the 200 Agency Mark[16:17] Doing Things That Don't Scale[17:15] Repairing Carrier Agent Relationships[18:38] InsurTech Competition for Carrier Investment[19:55] Planning Bold 2026 StrategiesSubscribe for more tactical insurance growth strategies and connect with Callan Harrington on LinkedIn to share your thoughts on this episode: https://www.linkedin.com/in/callanharrington

Callan Harrington sits down with Nick Golubitsky, VP of Revenue Operations at GreenSlate, for a deep dive into how AI is actually being used in go-to-market today. Nick brings over 8 years of revenue operations experience across multiple insurtech companies and shares real campaigns and tools he's implementing right now. This conversation cuts through the AI hype to focus on practical applications that are driving results.Nick walks through a live enterprise lead campaign using multiple AI tools, explains why conversational intelligence has become the gateway for sales teams to embrace AI, and how these tools are making sales reps more effective rather than replacing them. The discussion covers everything from automated lead qualification to proactive customer success initiatives powered by AI-generated insights.This episode delivers tactical insights for anyone wondering how AI is actually being implemented in revenue operations and what's possible today versus what's coming in the next few months.Key topics covered:[00:00] Intro[03:16] Salesforce Admin to Rev Ops Evolution[06:41] AI and Rev Ops Partnership Era[09:43] Competitor Campaign Using Multiple AI Tools[13:09] Native Hubspot vs Category Leaders[16:10] Prospecting Agent Research Capabilities[20:37] Conversational Intelligence Gateway Drug[23:05] AI Enhanced Sales Training Methods[26:01] Data Collection Without Resource Overhead[30:24] Insurance Tech Lessons from 5 Years Ago[35:02] Proactive Value vs Generic Outreach[36:48] Future of Rev Ops Role Evolution[42:18] Confidence Advice for Starting OutConnect with Nick on LinkedIn to learn more about his revenue operations strategies: https://www.linkedin.com/in/nickgolubitsky/Subscribe for more tactical insights from insurance growth leaders, and let us know in the comments what AI tools you're experimenting with in your go-to-market operations.

Host Callan Harrington sits down with Ryan Hanley, President of Linqura and one of the insurance industry's most recognized voices, to break down the content strategy that built his personal brand over 20 years. Ryan shares how he went from nearly being fired by his father-in-law to becoming a sought-after speaker and industry leader through consistent content creation.Ryan explains his unique approach to content development, filtering ideas through leadership topics and insurance applications to create wholly original takes. He reveals his current workflow using AI tools to streamline commenting and editing, allowing him to maintain consistent output across multiple platforms. The conversation dives deep into why Ryan believes personal branding is now mandatory for anyone in leadership positions, not optional, and how content serves as a trust-building mechanism that moves prospects closer to purchase before any sales conversation begins.This episode delivers actionable insights for insurance professionals and business leaders looking to build their personal brand and leverage content marketing for career growth.Key topics covered:[00:00] Intro[03:21] Why Ryan Started Creating Content for Insurance Agents[06:07] Being a Misfit in Traditional Insurance Sales[11:03] When Content Creation Started Working[16:02] Ryan's Current Content Strategy and Process[19:39] Video First Content Creation Approach[20:08] Personal Brand vs Business Marketing Debate[26:28] Content as Trust Building Before Sales Conversations[31:25] Is Personal Branding Mandatory for Success[36:58] Building Content From Scratch Today[42:07] Starting with Commenting Before Creating Posts[47:17] AI Hack for Automated Content Commenting[49:55] What Ryan Would Do Differently Starting OverConnect with Ryan Hanley on LinkedIn: https://www.linkedin.com/in/ryanhanley/Subscribe for more tactical growth insights from insurance and business leaders.

Callan Harrington returns from ITC Vegas with a critical observation that every insurtech needs to hear. Despite increased capital flowing into the market and genuine excitement around new technology, decision makers are completely lost trying to figure out what these companies actually do. When everyone claims to be "the AI company for insurance," the messaging becomes indistinguishable noise.Callan breaks down why this positioning crisis is happening and reveals the massive opportunity it creates for companies willing to get specific. He shares real examples from the conference floor, including how consultants are now stepping in as curators to help overwhelmed buyers navigate the sea of similar-sounding AI solutions. The episode covers tactical strategies for standing out, from owning specific use cases to building strategic partnerships that can unlock much larger deals.This solo episode delivers actionable insights for any insurtech struggling to differentiate in an increasingly crowded market.Key topics covered:[00:00] Intro[01:42] People are lost in insurtech[02:33] How we got here[04:20] AI companies trying to own everything[05:45] VC perspective on AI differentiation[07:07] Insurance's massive technology spending[08:19] Having AI is now table stakes[09:05] Decision maker fatigue and confusion[10:00] Consultants filling the curation role[11:09] Missing out on consultant relationships[13:28] What insurtech companies can do[14:43] Getting more specific with use cases[16:18] Huge opportunity for better positioning[17:56] Lean into partnership-led growth[18:45] Most exciting ITC despite confusion[19:51] Big opportunity for positioning winnersConnect with Callan Harrington on LinkedIn for more insurance growth insights: https://www.linkedin.com/in/callanharringtonSubscribe for more tactical insurance marketing strategies and growth campaigns that drive real results in the industry.

Callan Harrington sits down with Margeaux Giles, CEO of IRYS Insurtech, to break down their year-long rebranding process that transformed both their external presence and internal culture. Margeaux shares why rebranding felt necessary after 3 years of rapid startup growth and how the process became much deeper than choosing new colors and logos.The conversation reveals the unexpected internal benefits of rebranding, from aligning employees on the company mission to dramatically improving content quality. Margeaux walks through their discovery process, the challenges of getting executive team consensus, and how they developed their rallying cry, "step out of line", that now drives company culture. She also discusses the practical timeline challenges, the decision to keep their company name, and their strategic launch approach that treated the rebrand as a quarter-long marketing initiative.Whether you're considering a rebrand or simply want to understand how it impacts company culture, this episode provides tactical insights from a CEO who just completed the process with measurable results.Key topics covered:[00:00] Intro[03:42] Professional services vs SaaS company differences[06:21] Hard pivot leadership style challenges[08:03] Why IRYS needed a rebrand after 3 years[11:53] Brand discovery process and internal alignment[15:14] Finding the company's rebel archetype[17:08] Making final brand decisions through consensus[19:03] Internal culture impact of brand discovery[21:40] Step out of line rally cry development[24:10] Keeping the IRYS name during rebrand[27:20] Content quality improvement after rebrand[32:16] Authentic content vs AI-generated posts[34:59] What she would do differently[37:19] Perfect timing for rebranding doesn't existConnect with Margeaux Giles on LinkedIn: https://www.linkedin.com/in/margogiles/Learn more about IRYS at https://iryscloud.com/Subscribe to The Insurance Growth Lab for more tactical growth insights

Callan Harrington sits down with Alex Harris, co-founder of Fiat Growth and Fiat Ventures, to unpack how great partnerships actually drive growth. Alex shares the story of bringing together two major players in insurance, Lemonade and Bestow, and transforming that collaboration into a revenue engine, not just a press release.He explains how journey mapping, trigger-based campaigns, and data-driven targeting helped unlock meaningful customer adoption. Along the way, Alex opens up about his viral marketing roots and what the future of partnerships looks like in an AI-driven world.Key topics covered:[00:00] Intro[03:42] Viral video breakthrough[08:20] Full circle moment with Chime[14:19] Building Fiat Growth[17:56] Partnership strategy for Lemonade and Bestow[24:43] Driving real revenue from partnerships[26:02] Customer journey mapping for success[28:29] Life cycle marketing tactics and triggers[32:51] AI tools transforming services business[35:02] Target pregnancy prediction data story[37:34] Embracing AI without losing human connection[39:37] Events becoming more important than ever[40:22] Advice to younger selfConnect with Alex Harris on LinkedIn: https://www.linkedin.com/in/alexharrisjdmba/Learn more about Fiat Growth: https://www.fiatgrowth.com/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

Callan Harrington breaks down the evolving go-to-market landscape for insurtech companies, sharing insights from his presentation at InsureTech New York's Education Day. As founder of Flashgrowth, Callan examines what's stayed the same from 2024 and what's rapidly changing in 2025 as AI transforms sales and marketing strategies.Callan covers critical benchmarks for scaling revenue from zero to 1 million, 1 to 10 million, and beyond 10 million in annual recurring revenue. He explains when to hire your first sales reps and VP of Sales, and when the timing is right to scale. The discussion includes essential metrics like customer retention rates, quota attainment benchmarks, and the importance of crossing the chasm from early adopters to early majority customers.Key topics covered:[00:00] Intro[03:24] Zero to 1 Million Sales Benchmarks[05:05] When to Hire First Sales Reps[06:54] 1 to 10 Million Growth Stage[08:01] Hiring Your First VP of Sales[11:23] Scaling Past 10 Million Revenue[12:25] Golden Rule of Quota Attainment[14:05] Ideal Customer Profile Requirements[14:59] Crossing the Chasm Strategy[18:00] AI's Impact on Go-to-Market[19:45] Cold Calling Death Myths[21:13] Partnership Led Growth Rise[22:25] Revenue Leaders Need AI Skills[24:06] Things Are Moving Faster[25:38] Expert Status Requirements[27:04] Go-to-Market Headcount Predictions[28:40] Relationships as Future CurrencySubscribe for more tactical insurance growth strategies that cut through the noise and focus on what actually works.

Host Callan Harrington sits down with Chris Kessler, Chief Product and Platform Officer at Bold Penguin, for an in-depth look at enterprise solution selling. Chris brings a unique background in strategy consulting that has directly shaped how Bold Penguin consistently lands household names as enterprise clients in the insurance space. The conversation centers on Chris's detailed solutioning process, which goes far beyond typical sales approaches. He walks through his methodology of engaging with the right stakeholders, conducting strategic whiteboard sessions, and building comprehensive roadmaps that blend core product with custom services. He covers everything from identifying P&L owners with long-term mandates to navigating brutal procurement processes in the insurance industry.Key topics covered:[00:00] Intro[01:49] Solution in Enterprise Sales[03:42] How Chris Fell Into Insurance[08:15] Strategy Consulting to Corporate Strategy[13:38] Solution Process Deep Dive[16:00] Finding the Right Decision Makers[18:48] In-Person Strategy Sessions Matter[20:00] Whiteboarding Current State Process[24:28] Charging for Discovery Work[27:17] Building the Future State Roadmap[32:48] Procurement Doesn't Get Easier[36:15] Implementing Consulting Skills at Bold Penguin[39:07] Recognizing a Real Opportunity[42:24] Career Advice for Your Younger SelfConnect with Chris Kessler on LinkedIn: https://www.linkedin.com/in/kesslerchris/Learn more about Bold Penguin: https://www.boldpenguin.com/Subscribe for more tactical growth insights from insurance industry leaders, and leave a review if this episode helped you think differently about your acquisition strategy.

Callan Harrington sits down with Ido Deutsch, VP of Growth at Agentero, to break down one of the most successful (and shocking) paid media strategies for acquiring insurance agencies. Ido shares how he built a predictable and affordable machine generating leads via Facebook. He breaks down the mindset that led him to bet on paid social, the experimentation framework behind his campaigns, and why chasing “more leads” is the wrong strategy.For insurance companies looking to diversify beyond traditional outbound methods, this episode provides a proven roadmap for paid social success in a notoriously difficult B2B market.Key topics covered:[00:00] Intro[03:32] First Tech Company Origin Story[05:40] Building Solutions From Personal Pain Points[08:22] When to Build vs Buy Decisions[10:26] Understanding Your Audience is Everything[13:44] Insurance Experience Advantage in Sales[17:07] Career Pivot From Soccer to Tech[20:12] Builder Mentality and Risk Taking[22:46] Experimentation Framework for Growth[25:26] Facebook Lead Generation Strategy Launch[29:09] $30 Cost Per Lead Results[32:34] Why Facebook Works for Insurance Agents[33:17] Analytics and Optimization Process[35:52] Revenue Leaders Should Own Marketing Funnel[43:47] Ido’s Growth Journey at Agentero[46:43] Advice to Younger SelfConnect with Ido Deutsch on LinkedIn: https://www.linkedin.com/in/ido-deutsch/Learn more about Agentero: https://agentero.com/Subscribe for more tactical growth insights from insurance industry leaders, and leave a review if this episode helped you think differently about your acquisition strategy.

Callan Harrington sits down with Amber Wuollet, Director of Product & Lifecycle Marketing at Cowbell, to explore how thoughtful marketing can change the trajectory of an insurance product. After years of lackluster performance, Amber’s team uncovered insights that helped a struggling policy hit its 12-month sales goal in just 6 months, without changing a single feature.The conversation also touches on Amber’s career journey, including lessons from a launch that collided with COVID shutdowns and the practical steps she uses to uncover what really drives growth.Key topics covered:[00:00] Intro[02:38] Epic marketing fail during Covid[10:32] Early career ambition at 14[13:37] How 10 years in underwriting shaped marketing perspective[22:48] Product launch research strategy[26:29] Complete positioning overhaul eliminates complexity[28:01] 12-month goal achieved in 6 months[32:47] 30 customer interviews reveal key insights[35:33] Right-sized launch strategy for niche product[37:53] Product unchanged but messaging transformed results[43:34] Product marketing definition and role[49:28] Lifecycle marketing beyond product launch[53:09] Advice for younger selfThis episode delivers practical insights on customer research methodology, positioning strategy, and how to execute product relaunches that drive real business results.

Callan Harrington, Founder of Flashgrowth and host of That Worked, reflects on the journey of his podcast as he records its final episode before shifting to The Insurance Growth Lab. In this solo episode, he dives into the origins of the show, what it became, and why now is the right time to focus fully on the insurance space. With stories, founder-inspired lessons, and a glimpse into what’s next, Callan shares the evolution of the podcast.In this episode, you’ll learn:How That Worked began as a networking tool, and why it quickly became something more impactfulHow repeated founder advice led Callan to niche down into insurance, sparking major growthThe lessons and momentum gained from getting tactical and going deep with guestsWhat to expect from The Insurance Growth Lab, including a video-first format and industry focusHow vulnerability and consistency shaped the long-term success of the showFollow Callan on LinkedIn

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’s basketball team and later the Assistant Athletic Director at the University of Dayton. In this episode, you’ll learn:How to create work/life alignment How sports prepare you for startupsHow to evaluate potential employeesWhat to expect in the earliest stages of a company Why you need to have a bias for action in a startup Follow Matt on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

In 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. They also break down the 10-80-10 rule of delegation, an approach to outsourcing that helps creators and entrepreneurs focus on high-impact work. Plus, they dive into the role of relationships in business growth and discuss the balance between creative control and efficiency.In this episode, you’ll learn:Strategies for effective collaboration and outsourcingWhy repurposing content can supercharge engagementHow to leverage visual planning tools for content creationThe importance of structured ideation and content pipelinesThe 10-80-10 rule of delegation and how it optimizes workflowFollow Sullivan on TikTok and InstagramFollow Callan on LinkedInSubscribe to the Newsletter 

In 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 effectiveness both on stage and in the workplace, while Callan emphasizes the growing importance of human-driven insights in an AI-saturated environment. Together, they unpack how AI-generated search results are reshaping content discovery, highlight the practical benefits of delegation to reclaim valuable time, and offer candid observations about the world of LinkedIn thought leadership. In this episode, you’ll learn:The importance of outsourcing to reclaim time and focus on growth.Why improv training can enhance leadership, negotiation, and adaptability.How content creators can balance control with delegation for better output.How AI-generated search results are reshaping content discovery and online trust.Managing frustration and workflow efficiency in a high-demand creative environment.Follow Sullivan on TikTok and InstagramFollow Callan on LinkedInSubscribe to the Newsletter 

In 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 creative industries. Sullivan shares his perspective on balancing creative integrity with AI-driven scalability, the challenges of licensing digital likenesses, and why in-person entertainment might become even more valuable in an AI-saturated world. Callan and Sullivan also discuss their upcoming live comedy show, Corporate Takeover, and the creative process behind bringing corporate satire to the stage.In this episode, you’ll learn:The impact of AI on industries like acting, comedy, and digital mediaThe challenge of balancing creative ownership with AI-generated contentHow Sullivan and Callan are developing a live comedy show inspired by corporate cultureHow OpenAI’s deep research tool is reshaping competitive analysis and content preparationWhy AI-driven brand collaborations present both opportunities and ethical dilemmas for creatorsFollow Sullivan Finlay on TikTok and InstagramFollow Callan on LinkedInSubscribe to the Newsletter 

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 insights on how niching down can unlock exponential growth opportunities.In this episode, you’ll learn:The importance of industry expertise for differentiationWhy committing to a niche can accelerate word-of-mouth referralsWhy niching down feels risky but often leads to exponential growthHow segmentation and early adopters play a role in business successHow specialization simplifies decision-making and improves networkingFollow 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, 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-building plays a crucial role in expanding creative opportunities. Sullivan shares his insights on adapting to industry shifts, while Callan discusses adding instant value in business and the importance of strategic positioning. Together, they offer actionable advice on future-proofing careers and navigating an ever-changing digital world.In this episode, you’ll learn:How AI could redefine knowledge work and career stabilityThe power of niching down in business growth and creative careersStrategies for leveraging existing relationships to expand opportunitiesThe high-stakes TikTok bidding war and what it means for brands and creatorsHow content creators can diversify income streams and future-proof their careersFollow Sullivan Finlay on TikTok and InstagramFollow Callan on LinkedInSubscribe to the Newsletter 

Sriya 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 looks like.  How to develop a ‘prompt engineering’ skill set. How using your own product impacts your product roadmap. How to educate, train, and inspire customers to adapt cutting edge technology. Follow Sriya on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Scott 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 industry and was successfully acquired by Zywave in 2021. In this episode, you’ll learn:The power of narrowing your focus. How innovating internally can differentiate your service model. How to test if a product is ready for you to start selling externally. When it makes sense to transition from bootstrapping to raising capital. How to approach partnerships and acquisitions with competitors without sharing sensitive information. Follow Scott on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Dan 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 ($100M) from fintech investors Accel and Sofi. Dan has also been named in the Smart 50 Class of 2022, 40 Under 40, Future50 Class of 2021, and the #4 CEO by Glassdoor.In this episode, you’ll learn:How to adapt from a B2B to B2C mindset. When to acquire externally versus build internally. How an entrepreneurial culture empowers high performers. How to grow market share in a down market through acquisition. How avoiding over-accommodating a seller in an acquisition leads to long-term success. Follow Dan on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Tom 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 really good at grows profits. The value of seeking out educational opportunities later in life. How to maintain a balance between operational excellence and innovation. How to build a business grounded in courage, empathy, and doing the right thing. The importance of surrounding yourself with a diverse team with complementary skills. Follow Tom 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 

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 

David 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, David was Chief Actuary at Clearcover, a personal auto insurtech startup in Chicago. David is also a Fellow in the Casualty Actuarial Society and has an extensive background in creating and managing insurance programs.In this episode, you’ll learn:How to evaluate a potential co-founder. How to structure a consult-to-hire team before raising capital. How robust data collection can help you stand out from the competition. How a strong and quick offboarding process can mitigate hiring mistakes. How to ensure you have the right team members for the current stage of your business. Follow David on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Ry 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 million dollars. In this episode, you’ll learn:How to navigate the difficulties of layoffs. The value of selling 5% of your shares during Series B. The importance of letting your team review you as a CEO. How to build strong leaders through clear expectations of roles. The importance of paying it forward within your entrepreneur community. Follow Ry on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Todd 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 systems that deliver business value and scale without excessive costs. Prior to Test Double, Todd worked as a Vice President at Pillar Technology. In this episode, you’ll learn:How to secure speaking engagements by building your personal brand. The value of organic relationship building to procuring initial client engagements. How an Employee Stock Ownership Plan (ESOP) can attract and retain top talent. An overview of the tactical steps to set up an ESOP, the upfront costs, and long term benefits. How strict profit margin goals can help you avoid layoffs and stay competitive by investing money back into the business. Follow Todd on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

Joe 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 was selected as a member of the Young American Leaders Program at Harvard Business School.In this episode, you’ll learn:The healing power of writing and journaling The power of sharing your story to move othersWhat it’s like working for a mission-driven organization Why there is nothing more important than friends and family The importance of prioritization as you take on more responsibilitiesFollow Joe on LinkedInConnectFollow Callan on LinkedInSubscribe to the Newsletter 

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