Lessons From the Front Lines of Building an AI Startup

Kameale Terry set out to fix EV chargers everyone insisted weren't broken. Today, she’s CEO and Co-founder of the startup ChargerHelp, the undisputed category leader in reliability-as-a-service for EV chargers. She joins Kate to share what it takes to scale, her path to a successful Series A, how AI has been instrumental in the company's growth, and her infectious enthusiasm for building!=== CHAPTERS ===01:40 — The EV Charger Reliability Issue That Sparked the Idea02:42 — Why She Took the Leap03:50 — Evolving the Solution to a Complex Problem05:55 — Creating a Whole New Market Category08:24 — Trusting Your Gut Despite Naysayers09:30 — Feel Your Customer’s Pain & Build for It10:10 — Lean Into Your Story to Convey Your Value10:59 — How She Improved Her Pitching Skills13:00 — What to Look for in a Co-Founder14:49 — Their Fundraising Journey16:00 — Positioning ChargerHelp as the Market Leader17:35 — Scaling ClimateTech Through Policy Swings21:45 — Using AI to Stay Ahead of the Competition25:00 — Advice for Founders: Build, Build, Build26:30 — It's Okay That It's Hard27:20 — Where to Find ChargerHelpStay connected with our host, Kate Adams, https://www.linkedin.com/in/kateadams22/🔗Learn more ChargerHelp at: https://www.chargerhelp.com/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

Medha Agarwal, General Partner at defy.vc, joins Kate to share how founders can stand out to investors in an AI-saturated market, what she looks for before writing a check, why founder-market fit matters, and how AI is reshaping everything from startup defensibility to pricing models. She also offers a look at how devy.vc supports founders well beyond capital.Full show notes, transcript, and companion article: https://burklandassociates.com/podcasts/how-to-stand-out-to-investors-in-an-ai-saturated-market==== Chapters ====01:26 — Medha's Path From Entrepreneur to Venture02:48 — What Makes defy.vc Different Than Other VC Firms03:52 — Their Investment Focus06:49 — More Than a Check: How They Partner with Founders10:44 — Building Trust and Providing Honest Feedback13:07 — What Medha Looks For Before Writing a Check15:12 — Does defy.vc Evaluate AI Startups Differently?16:23 — How VCs Are Using AI17:19 — Advice on How to Stand Out to Investors in an AI-Saturated Market21:09 — More Startups, More Revenue — But What Happens Next?24:14 — What Makes Medha Genuinely Excited About Startups Today26:31 — Don't Forget to Zoom Out and Think Long Term27:53 — Hiring Is a Superpower, Especially Right Now29:38 — Where to Find Medha and defy.vc----Stay connected with our host, Kate Adams, here: https://www.linkedin.com/in/kateadams22/🔗 Learn more at https://defy.vc/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

Our 150th episode is a big one. Kate sits down with Carl Fudge, Founder and CEO of Presentation Mode, who's helped startups raise over $1 billion in venture capital. Carl reveals why most pitch decks fall flat, the "why now" argument nearly every founder overlooks, and why logic alone isn’t enough to win investors over. Tune in to hear lessons from years spent helping founders get to “yes.”Full show notes, transcript, and companion article: https://burklandassociates.com/podcasts/why-investors-say-no-to-your-pitch-deck-and-how-to-fix-itChapters00:00 – Introduction to Carl Fudge & Presentation Mode01:10 – Carl's Background: Psychology, McKinsey, IDEO & Catching the Startup Bug02:58 – What Presentation Mode Actually Does05:50 –  How They Help Founders Craft Compelling Pitches07:50 – Why They Bring in a Trained Actor11:35 – The Must-Have Components of Every Pitch Deck13:44 – The "Why Now" Argument Most Founders Overlook15:30 – Logic vs. Feeling: The Psychology of Investor Decisions17:09 – The Mac vs. PC Lesson on Selling Features vs. Selling Feeling19:19 – Less Is More: How Much Detail Should Be on a Slide20:50 – Shifting the Power Dynamic With Investors22:50 – Fundraising Advice for AI-Native Startups vs. Non-AI Startups26:10 – Storytelling: More Than a Fundraising Tool----Stay connected with our host, Kate Adams, here on LinkedIn! 🔗 Learn more about Presentation Mode: https://www.presentationmode.co/

Winning over investors as a healthtech founder requires fortitude, relentless pitching, and the ability to tell a hard "no" from a "not right now."In this episode, Kate sits down with Melissa Hanna, co-founder and CEO of Mahmee, a healthcare platform transforming how families experience pregnancy and postpartum care. Melissa pitched 500 to 1,000 investors before landing backers like Mark Cuban, Serena Williams, and Steve Case, plus a Series A led by Goldman Sachs.Melissa walks us through how Mahmee built the technology and workforce infrastructure that now has 70 million lives under contract. She also opens up about the fundraising grind and shares her perspective on AI's role in healthcare.Tune in to hear:Strategies for fundraising in this challenging marketHow founders outside the AI space can still leverage AIAn insider's perspective on where AI should and shouldn't be used in healthcareWhy core values are key, even at early-stage startupsMelissa’s advice to fellow founders: accept the struggle, and commit to a problem worth solving.Don't miss this conversation with a founder proving healthcare can be both high-tech and deeply human.---- Stay connected with our host, Kate Adams, on LinkedIn🔗 Learn more about Mahmee at: https://www.mahmee.com/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts==== Chapters ====00:17 – Fundraising for a HealthTech Startup in the AI Era02:33 – What Is Mahmee? The Platform Closing Gaps in Maternal Care04:39 – The Inspiration Behind Mahmee: A Mother's Influence06:09 – Taking the Leap: Building the Founding Team07:11 – The US Maternal Health Paradox: Spending the Most, Getting the Worst08:54 – Creating a Healthcare Platform That Adapts to Each Family's Journey10:00 – Stumbling Into New Opportunities11:18 – Where Mahmee Is Today: 70 Million Lives Under Contract16:19 – Where AI Should and Shouldn't Be Used in Healthcare18:38 – The Fundraising Journey: Pitching Hundreds of Investors22:20 – Core Values Aren’t Just for Big Companies25:35 – Parting Advice for Founders: Accept the Struggle27:33 – Where to Find Mahmee

In this episode of Startup Success, we sit down with Steve Lord, COO and Chief Knowledge Officer at Burkland, for our quarterly update. Steve joins us to break down what's happening in the funding landscape, what founders should have on their radar, and where things are headed next.Steve unpacks a busy Q2 marked by geopolitical volatility, shifting interest rate expectations, and a VC market that may finally be turning a corner. He explains how the stock market impacts VC cycles, and why founders shouldn't panic over a single bad day in the markets. He also makes the case for why trillion-dollar IPOs — starting with SpaceX, and potentially OpenAI and Anthropic — could unlock more value than all VC-backed IPOs this century combined, recycling enormous liquidity back into the startup ecosystem.We discuss:Why using an AI-generated pitch deck will hurt your chances with VCsThe good news: 2026 is on track to be a record year in first financings for startupsThe state of interest rates, inflation, and why a Fed cut won't affect your startup in the short termAI startups are still dominating VC funding — here's where the opportunities are for everyone else If you're trying to make sense of where the funding market stands right now, this episode is the shortcut. Steve lays out the macro forces in plain terms, and tells you what it means for your next raise.====Chapters====[00:18] Q2 Recap: Geopolitical Volatility and Market Crosscurrents[02:15] Listener Question: Does the Stock Market Impact VC Cycles?[05:50] The IPO Market is Back — and It Will Give VCs More Liquidity[06:16] What the Power Law of VC Means for Founders Right Now[07:50] Upswing in VC Funding Activity [07:00] AI Funding Still Dominates[09:30] Could Be a Record Year for First Financings for Startups[10:16] The State of Smaller VC Firms and Where Opportunity Still Exists[12:51] What’s Up with the Economy, Inflation, and Interest Rates?[16:50] Advice for Founders Heading Into Q3[18:54] Why AI-Generated Pitch Decks Are Working Against Founders----Stay connected with our host, Kate Adams, here on LinkedIn! Learn more about Burkland at: https://burklandassociates.com/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

In this episode of Startup Success, we sit down with Jaclyn Johnson, founder of Create & Cultivate and co-founder of the angel investing platform Cherub, for a conversation about scaling a business, navigating an exit, and the future of early-stage investing. Jaclyn shares how she built Create & Cultivate into a multi-million-dollar, bootstrapped company, why she made the difficult decision to sell, and what prompted her to buy back the company a few years later. She offers an honest look at the tradeoffs of private equity and the factors that can make or break a deal.Between the exit and the buyback, her work as an angel investor and mentor to early-stage founders led her to co-found Cherub, a platform that connects founders with angel investors they'd never reach otherwise.We discuss:The realities of selling to private equity — and what founders often overlookWhat founders need in place before they start raising capitalHow the fundraising landscape for early-stage founders is changingIf you're building your first company, preparing to raise capital, or thinking about an exit, this episode offers hard-earned lessons from a founder who has been on both sides of the table.----Stay connected with our host, Kate Adams, here on LinkedIn! 🔗 Learn more about Create and Cultivate at https://www.createcultivate.com/Learn more about Cherub at https://www.investwithcherub.com/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

Ahmed Rashad started his career on an oil rig, taught himself to code, and went on to build and sell a company. After stops at Oracle, MIT, McKinsey, Amazon, and Scale AI, he founded Perle to solve a problem he kept running into: the AI data gap.Perle builds specialized training data for AI models in fields like medicine and linguistics — the niche areas where general AI struggles.Despite the anxiety around AI, Ahmed believes the upside far outweighs today’s disruption. Faster development doesn't shrink markets; it expands what's possible. In his view, AI isn't replacing human potential. It's amplifying it.Tune in to hear:Why the right VC partner matters more than the biggest checkThe 4 things founders should never delegateHow to keep investors engaged and informedWhat Arabic’s 22+ dialects reveal about the depth of the AI data gapWith experience at some of the world’s leading companies and now as the founder of an exciting AI startup, Ahmed has valuable insights on today’s startup ecosystem.Don’t miss this episode for practical, hard-earned advice from a founder who has been in the thick of it since day one.====Chapters====00:18 – Meet Ahmed Rashad, Founder & CEO of Perle01:15 – From Oil Rig to Software: Ahmed's Unlikely Origin Story02:34 – What Perle Does and the Problem It's Solving03:35 – Why This Problem Was Personal04:35 – Use Cases: Healthcare, STEM, and Linguistics05:02 – The Arabic Language Challenge: 22 Dialects and Counting07:22 – How the Rapidly Changing AI Landscape Is Impacting Perle09:16 – Fundraising Advice: The Four Things Founders Should Never Delegate10:40 – Why the Right VC Beats the Highest Valuation11:30 – What to Look for in an Investor Relationship12:09 – How to Communicate Effectively with Your Investors13:40 – The Reality of the Founder Journey: It's Never a Straight Line16:36 –Why Ahmed is So Optimistic About AI18:27 – What Concerns Ahmed About AI19:47 – The AI Slop Problem20:53 – Final Advice for Founders: Take Care of Yourself22:42– Where to Find Ahmed and Learn More About Perle----Stay connected with our host, Kate Adams, here on LinkedIn! Learn more about Perle: https://www.perle.ai/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

Jonathan Aberman has seen the startup world from nearly every angle: VC lawyer, investor, business school dean, and innovation policy advisor. Now he's a founder himself, building Hupside, an AI company focused on measuring "original intelligence."That 360-degree perspective of the startup ecosystem makes his take on the current AI moment especially valuable. The market is noisy. Capital is concentrating. Investors are excited, skeptical, and cautious at the same time. AI tools are making it easier than ever to build, but harder than ever to stand out.We discuss:What the AI bubble means for founders raising capital todayWhy many founders confuse fundraising with validation"Signal collapse" and why creativity is the next major startup advantageWhy Jonathan built Hupside to measure human originality in an AI worldIf you're building with AI, raising capital, or trying to stand out in a crowded market, this episode is worth your full attention.---Stay connected with our host, Kate Adams, here on LinkedIn! Learn more about Hupside: https://www.hupside.comThis episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

What does it actually take to be investment-ready in today's market? In this episode, Kate sits down with Jim Ferry, Partner at Volition Capital, a growth equity firm known for backing high-growth, founder-owned, capital-efficient businesses.Jim reveals what he looks for in a founding team, the most common mistakes he sees in pitch decks, and how the bar for raising capital has changed in the age of AI. He also explains how his firm is building AI fluency internally — and why the "defensible moat" question is now front and center in their investment decisions.We also cover:What Volition learned about successful founders after analyzing 100+ founder attributes across its portfolioHow to build a durable company when engineering is no longer a barrier to entryThe right way to present your TAM to build credibility with investorsHow investors are using AI to source and evaluate dealsNo matter where you are in your fundraising journey, Jim's perspective offers a valuable window into how top investors are thinking right now.----Stay connected with our host, Kate Adams, here on LinkedIn! Learn more about Volition Capital: https://www.volitioncapital.com/This episode is produced by:Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas MediaAngela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts

In this episode of Startup Success, host Kate sits down with Tony Jamous, Co-Founder and Executive Chairman of Oyster, and Hadi Moussa, the company’s newly appointed CEO, for a refreshingly honest conversation on scaling a global company— and knowing when it’s time to bring in new leadership.Tony shares the personal journey behind one of the hardest decisions any founder can make: stepping aside as CEO, and why putting the mission ahead of ego sets great founders apart. And Hadi explains how he’s approached the transition to ensure a successful handoff.We discuss:The moment Tony knew it was time to hand over the CEO roleHow to manage leadership transitions with intention and transparencyCommunicating the change in a way that builds trust and signals strengthWhy global hiring is a competitive advantage in the age of AIWhether you're navigating growth, thinking about leadership evolution, or rethinking how to build a distributed team, this episode offers a thoughtful look at what it really takes to scale—with the right people, in the right roles, at the right time.----Stay connected with our host, Kate Adams, here on LinkedIn! Learn more about Oyster at https://www.oysterhr.comThis episode is produced by Brenda Hernández Jaimes of Ellas MediaPost-Production by Angela R. Chong of Amplify Podcasts