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cover art for EP021: 1 Minute to Pitch, ft. Mike MacCombie of Generous Ventures

The Feedback Loop

EP021: 1 Minute to Pitch, ft. Mike MacCombie of Generous Ventures

Season 1, Ep. 22

3 startup founders have a minute each to pitch their business and their vision of the future. Then, they receive unfiltered feedback on both their concept and their storytelling.


Because the thing that can hold even the best founders back from reaching their ambition? Their pitch. Whether a startup founder is raising money, recruiting a team, or selling their product, it's the pitch at the start of any given conversation that starts them on a journey to success.


As always, hosted by Sherveen Mashayekhi, Founder & CEO of Free Agency. Follow him on X at @Sherveen.


Today's guest investor was Mike MacCombie, General Partner at Generous Ventures. Mike has spent the past 8 years in venture capital – as an investor, operating + platform partner, community builder, and superconnector, supporting founders at the earliest stage. Find him on X at @MikeMacCombie.


To attend The Feedback Loop in-person or apply to pitch as a founder, head to afterfeedback.com.


Thank you to all of the brave founders who participated in this episode. The Feedback Loop is dedicated to creating an engine of support for startup founders attempting to change the way the earth spins. We're on your side.

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  • 73. 500 Fertility Clinics in US Serving 350M People!?

    19:58||Season 1, Ep. 73
    One startup founder has 60 seconds to pitch to two venture investors!And today, we’ve got a founder tackling a critical – yet often overlooked – health challenge: fertility care.It’s Episode 072 of The Feedback Loop, and it’s Josh pitching his vision for an all‑in‑one operating system that could reshape how fertility clinics and OB‑GYNs work together.Josh’s idea? Reduce the friction and stress of fertility treatments by offering a centralized clinic OS and patient app – empowering specialists to focus on advanced IVF procedures while everyday OB‑GYNs handle routine steps. In a country with just 500 fertility clinics serving a massive population of 350M+(almost 20% of the population experience infertility issues), Josh believes this can help more hopeful parents access care closer to home.But is this strategy too complicated to scale? While the goal of democratizing fertility is compelling, investors wonder: do you double down on software for existing clinics, or pivot toward a consumer‑facing approach for patients directly?More on our guest investor for the episode:​Ihar Mahaniok is Managing Partner at Geek Ventures, which he founded in 2021 to support immigrant entrepreneurs building at the pre-seed and seed stage. He’s made more than 200+ investments over the past decade, and has invested early in companies like Instacart, People.ai, Chainalysis, PandaDoc, and Airbyte, to name a few.Follow IharLinkedIn: https://www.linkedin.com/in/mahaniokX (Twitter): https://x.com/mahaniokFollow our host, Sherveen:LinkedIn: https://www.linkedin.com/in/sherveenmX (Twitter): https://www.x.com/sherveenWe dive into:Clinic OS vs. Patient App – Which aspect of Josh’s platform is most crucial for growth? Is it the back‑end or the consumer experience?Bridging the Fertility Desert – The majority of America lacks access to IVF. Can Josh’s platform turn local OB‑GYN offices into mini‑fertility centers?Market Size & Go‑to‑Market – Only 1,250 fertility experts serve a massive patient base. Is Josh’s plan to integrate with OB‑GYNs realistic—or too complex?10-Year Vision vs. Immediate Traction – Investors push for a clear roadmap: focus on servicing 500 clinics first, or begin weaving in telemedicine and at‑home tech now?Josh Gottesman, founder of Embie Clinic: https://www.linkedin.com/in/josh-gottesman1Drop a comment – feedback is the building block for builders everywhere!
  • 72. Yet Another AI Voice Agent?

    14:24||Season 1, Ep. 72
    1 startup founder has 60 seconds to pitch to 2 venture investors!And today, we've got a startup founder who has been in real estate for most of his career tackling an age-old problem in for brokers in his industry: wasted leads.It's Episode 071 of The Feedback Loop, and it's Gregory Maro pitching QalifAI!Gregory is building an AI agent trained on years of high-performing sales calls, capable of texting, calling, following up, and updating CRM notes just like a top-notch ISA (inbound sales agent).But is it enough to stand out when LLM-powered solutions are flooding the market? Venture capitalists hear a new AI startup pitch every 7.9 seconds (it's a fact, don't look it up though). Can Gregory tell a story about a data advantage that can hold up versus the rest of the market?But what does it take to make an AI company truly venture‑scale?As our panelists note, many founders are pitching GPT‑powered solutions – and investors are tired of “just another chatbot.” Gregory’s challenge is to prove a lasting competitive edge: is it the domain expertise and data, the deeper workflow integrations, or a broader vision that extends well beyond real estate?More on our guest investor for the episode:​Ihar Mahaniok is Managing Partner at Geek Ventures, which he founded in 2021 to support immigrant entrepreneurs building at the pre-seed and seed stage. He’s made more than 200+ investments over the past decade, and has invested early in companies like Instacart, People.ai, Chainalysis, PandaDoc, and Airbyte, to name a few.Follow IharLinkedIn: https://www.linkedin.com/in/mahaniokX (Twitter): https://x.com/mahaniokFollow our host, Sherveen:LinkedIn: https://www.linkedin.com/in/sherveenmX (Twitter): https://www.x.com/sherveenWe dive into...Training Data & Proprietary Advantage: Gregory emphasizes his mountain of real estate sales calls and messages. But will GPT’s rapid evolution make specialized datasets obsolete? Investors weigh how to build a moat in a sector evolving at breakneck speed.AI Wrappers vs. Full Workflows: Embedding an AI agent into the full sales lifecycle might create more stickiness than a point‑solution. Is Gregory’s bigger opportunity a platform that integrates deeply with CRMs, analytics, and post‑sale follow‑up?Venture Capital Realities: When is raising VC essential, and when might it be an overreach? Our panel tackles how founders should differentiate a potential “cash flow” business from a truly venture‑scale opportunity – especially in a market buzzing with AI hype.Real Estate’s Scaling Potential: Gregory sees a roadmap through rentals, commercial real estate, and ancillary services like mortgage and insurance. Is that enough to entice investors searching for billion‑dollar outcomes, or should he focus on conquering one niche first?Gregory Maro, co-founder of QalifAI: https://www.linkedin.com/in/gregory-maroDrop a comment – feedback is the building block for builders everywhere!
  • 71. He Has 60 Seconds to Pitch – Are These 2 Investors Into It?

    19:10||Season 1, Ep. 71
    Otto wants to build an AI platform to shake up the legacy industry of legal research. Can he get busy attorneys and legal services companies – reliant on familiar tools and workflows –- to switch over to his product?On Episode 070 of The Feedback Loop, that's what we get into!Otto von Zastrow is building midpage. Instead of spending weeks sifting through Westlaw or LexisNexis, he wants lawyers to search, read, and organize thousands of cases in a connected workflow – featuring LLM-fueled tags, question--asking, parallel prompting, and more.Can his 'Notion or Figma-style' approach offer a big enough leap over incumbents to make this interesting to our investor panel?We get into:Legal Research, Reinvented – Why building a better search bar isn’t enough to win over law firms and how a collaborative, AI‑driven approach may tip the scales.Owning the Workflow – From daily case‑tagging to drafting briefs, Otto envisions a single tool that captures the entire journey – is that a clear pitch that venture capitalists can understand?The Case for Data Supremacy – Scraping 500+ websites and linking case law with AI is no trivial feat, but is it the true moat that disrupts the duopoly?Startup Pitch Essentials – Investors push Otto to share a compelling vision beyond “search.” How can midpage become the Figma of legal research and drafting?Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.Follow SherveenLinkedIn: https://www.linkedin.com/in/sherveenmX (Twitter): https://www.x.com/sherveenMore on our guest investor for the episode:​Ihar Mahaniok is Managing Partner at Geek Ventures, which he founded in 2021 to support immigrant entrepreneurs building at the pre-seed and seed stage. He’s made more than 200+ investments over the past decade, and has invested early in companies like Instacart, People.ai, Chainalysis, PandaDoc, and Airbyte, to name a few.Follow IharLinkedIn: https://www.linkedin.com/in/mahaniokX (Twitter): https://x.com/mahaniokOtto von Zastrow, founder of midpage: https://www.linkedin.com/in/otto-von-zastrow-631b74113Drop a comment – feedback is the building block for builders everywhere!
  • 70. Multiplayer Journaling & an AI CFO for Restaurants, ft. Ihar of Geek Ventures

    29:54||Season 1, Ep. 70
    In Episode 069 of The Feedback Loop, we meet two bold founders pitching live: one harnessing real‑time wearable data to optimize your daily schedule, the other building a finance platform to help restaurant owners avoid costly losses.First Pitch: Lifestack – AI‑Powered ProductivityFounder Nao Yukawa wants to revolutionize daily calendars by syncing them with your Oura Ring, Apple Watch, Whoop, and more. Imagine factoring in your heart rate, sleep quality, and circadian rhythm so you tackle deep work at your peak and schedule “recovery breaks” before burnout strikes. But with so many calendar startups in Silicon Valley’s “tarpit,” can Lifestack stand out – or will it sink like so many scheduling tools before it?Second Pitch: Munch Insights – Restaurant Finance RebootFounder Daohao (“Dao”) Li faced the harsh reality of running a million‑dollar restaurant that still lost $40k. Now, he’s on a mission to give busy operators an intuitive dashboard for tracking cash flow, inventory, and revenue ops. Will restaurant owners – already drowning in apps – embrace one more platform? And is Dao’s bigger vision compelling enough for VCs and tech investors to see a path to venture‑scale success?We Explore:Health‑Informed Productivity: Can real‑time biometrics truly upgrade your schedule, or are we in an era of diminishing returns on wearables data?Scheduling’s “Tarpit” Problem: Why do so many calendar startups struggle to stand out, and how can Nao convince investors there’s real opportunity here?Restaurant Margins & Missed Metrics: Learn how Dao’s experience of “hidden losses” opened his eyes to the chaos many operators face – and the uphill battle of convincing them to adopt new tools.Paths to Scale: From enterprise partnerships to potential financing add‑ons, the investors weigh how each founder can pitch a bigger vision that’s still grounded in real‑world needs.Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.Follow SherveenLinkedIn: https://www.linkedin.com/in/sherveenmX (Twitter): https://www.x.com/sherveenMore on our guest investor for the episode:​Ihar Mahaniok is Managing Partner at Geek Ventures, which he founded in 2021 to support immigrant entrepreneurs building at the pre-seed and seed stage. He’s made more than 200+ investments over the past decade, and has invested early in companies like Instacart, People.ai, Chainalysis, PandaDoc, and Airbyte, to name a few.Follow IharLinkedIn: https://www.linkedin.com/in/mahaniokX (Twitter): https://x.com/mahaniokDaohao Li, founder of Munch Insights: https://www.linkedin.com/in/daohao-li-969bbb181
  • 69. 2 Startups on Time: AI for Timesheets, Wearables-based Scheduling

    37:14||Season 1, Ep. 69
    In Episode 068 of The Feedback Loop, we encounter two ambitious founders rethinking productivity – one aiming to free lawyers and consultants from the drudgery of manual timesheets, the other harnessing real‑time health data to optimize daily schedules.First, we meet Joseph Frantz from TimeSentry, whose AI-driven platform automatically logs your billable hours by syncing with Gmail, Outlook, Slack, and more. For the millions who dread rebuilding their workday from memory, TimeSentry offers a frictionless alternative – but can it handle compliance, integrate with entrenched tools, and compete with the time-tracking giants?Next, we hear from Nao Yukawa, co-founder of Lifestack. His AI‑powered calendar app syncs with wearables like Oura Ring and Apple Watch, dynamically adjusting your schedule around sleep metrics, stress levels, and circadian rhythms. But is the “quantified self” movement finally ready for prime time – or are busy professionals too cautious to let AI shuffle their workdays?We explore:• The Hidden Cost of Time Tracking: How AI might rescue lawyers and freelancers from the inefficiencies of six‑minute increments.• Data as the Next Productivity Frontier: Whether heart rate and sleep metrics truly improve performance – and how accurate wearables really are.• Adoption and Monetization Hurdles: From privacy and compliance in legal contexts to user skepticism about letting AI dictate their day.• Bridging New Markets: Could TimeSentry’s convergence of “time buying” and “time selling” spark the next big enterprise solution? And is Lifestack onto a universal scheduling tool?• And will venture investors see the nuances in these startup's operating models, demographic nuances, and integration dependencies – and how does Sherveen suggest they evolve their story for the early stage environment?Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.Follow Sherveen:LinkedIn | X (Twitter)A big thank‑you to Joseph and Nao for stepping into the spotlight. Subscribe for more behind‑the‑scenes founder pitches and unfiltered investor feedback – sometimes the biggest opportunities are hiding in the daily grind.Disclaimer: This content is for educational purposes only and does not constitute investment advice. Always do your own research before making any investment decision.Connect with the Founders:• Joseph Frantz, TimeSentry• Nao Yukawa, Lifestack
  • 68. 2 Startups: Social Network for Old People & Scheduling Platform for Parents

    32:26||Season 1, Ep. 68
    In Episode 067 of The Feedback Loop, we meet two determined startup founders pitching live – one tackling the loneliness epidemic among seniors, the other streamlining the chaos of youth sports scheduling for busy families.First, we hear from Fernando Dellepiane, co-founder of Vermut, who’s building a community-based app designed to keep seniors socially active (community as medicine). Loneliness can be as devastating to health as smoking a pack of cigarettes a day, and Fernando believes his solution can curb dementia risk while unlocking valuable data for insurers, banks, and public agencies. With over 100,000 users in Spain and several million dollars raised, he now sets his sights on the U.S. – but can Vermut’s European success translate across the Atlantic?Next, we meet Zoya Lehrer, co-founder and CEO of Orgo, whose scheduling platform aims to tame the “accordion of time” for active families, starting with youth sports. The pain is obvious for parents juggling endless carpools and game schedules, but even Zoya acknowledges the challenges of changing user behavior, integrating with current calendaring tools, and building a startup in a space known for messy logistics. Will her approach to “logistics as a service” and partnerships open the door to bigger enterprise opportunities?We explore:• Social Isolation’s Real Health Impact: How Vermut hopes to prevent dementia by driving authentic, in-person social engagement – and the hurdles to winning over older Americans. • The Ultimate Family Juggle: Orgo’s plan to coordinate countless tasks, from who's driving to when to leave and what to bring – all synced to the digital world parents already use. • Monetization and Scaling: Both founders share how they plan to generate revenue while meeting real-world adoption hurdles – from shy seniors to time-strapped moms and dads. • Hard Questions, Real Feedback: Tackling investor skepticism and cultural differences – can seniors in the Bronx embrace an app built in Barcelona, and will suburban families pay for scheduling peace of mind? • The Reality of Behavior Change: Both founders face the hard truth that great ideas aren't enough. Winning adoption among older adults and overwhelmed parents demands frictionless design, emotional resonance, and relentless user trust.Whether you're raising venture capital, are an investor yourself, or are an operator within a company in the tech industry, the cutting edge is the best place to learn. We highlight the stories of founders building startups on the edge.Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.Follow Sherveen:LinkedIn | X (Twitter)A big thank you to Fernando Dellepiane and Zoya Lehrer for stepping into the spotlight. The Feedback Loop is here to sharpen your pitch, refine your go-to-market strategy, and deliver real-world investor insights. Subscribe for more candid, actionable feedback for startups.Disclaimer: This content is for educational purposes only and does not constitute investment advice. Always do your own research before investing.Connect with the Founders: • Fernando Dellepiane (Vermut) • Zoya Lehrer (Orgo)
  • 67. Split Your Home v Your Land, & Another AI Marketing Startup?

    35:02||Season 1, Ep. 67
    In Episode 066 of The Feedback Loop, we meet two ambitious startup founders pitching live – one shaking up real estate affordability, the other tackling the crowded AI marketing landscape.First, Stuart Allan from Cedar introduces an innovative solution: splitting home ownership into house and land, aiming to cut prices in half. But can this leasehold concept, popular abroad, really work in the U.S., and is it robust enough to survive economic turbulence?Then we dive into the crowded world of AI-driven marketing startups with Brooke Yoakam, founder of AvidAI. Her vision? Replace traditional agencies with AI agents to boost lean teams’ growth. But with so many similar pitches, how does Brooke prove her company is unique – and can she realistically deliver on fully automated marketing?We explore:Real Estate’s Big Unbundle: How Cedar's separation of land and home could make housing radically cheaper – and why investors may still be skeptical.AI Marketing Saturation: AvidAI wants to eliminate the need for costly agencies and extensive marketing hires. But is a hybrid model (AI plus humans) the secret to success, or just a temporary workaround?Navigating Pitch Challenges: Both founders face tough investor feedback – learn how they tackle legal, operational, and competitive skepticism head-on.Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.Follow Sherveen:LinkedIn | X (Twitter)Thank you to Stuart Allan and Brooke Yoakam for stepping into the spotlight. The Feedback Loop is here to sharpen your pitch, refine your go-to-market strategy, and deliver real-world investor insights. Subscribe for more candid, actionable feedback for startups.Disclaimer: This content is educational only and does not constitute investment advice. Always conduct your own research before investing.Connect with the Founders:Stuart Allan (Cedar)Brooke Yoakam (AvidAI)Drop a comment – feedback is the building block for builders everywhere!
  • 66. 2 founders building for themselves first

    33:31||Season 1, Ep. 66
    What happens when you build a startup targeted at... yourself? On today's episode of The Feedback Loop, two founders built their business to fix issues in their own industry.First, a longtime NYC nanny reimagines the family-caregiver dynamic – building a platform that prioritizes both sides for better, more personal childcare matches. Then, a sports-tech entrepreneur unveils a mobile-first booking and socials & replay system for sports clubs, drawing on his team's experience building a ping pong platform (yes, really) and building apps like Equinox and Nike+ Running.Each founder has just a minute to pitch, followed by candid feedback from our resident investors. If you’re wrestling with marketplace strategy or bridging digital and physical experiences, you’ll see how to translate insider insights into a pitch that hooks investors, solves real pain, and drives adoption.Time for Episode 065 of The Feedback Loop!The investor feedback comes from our host, Sherveen Mashayekhi, founder and CEO of venture-backed Free Agency. He's also an angel investor and an LP in multiple venture funds. Each week, he's joined by a rotating seat featuring a guest venture investor, and this week, that's...Guest Investor: Lauren Reeves​Lauren Reeves is an Investor at MGV, an early stage SaaS fund based in SF and NYC. She also leads the team's east coast startup ecosystem initiatives. She brings a unique technical background to the judges' table — having previously been a software engineer building in AI, ML, and at notable companies like BlackRock, Postmates, and Alto Pharmacy.Follow Lauren on LinkedIn: https://www.linkedin.com/in/lauren-a-reevesFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmFollow Sherveen on X (Twitter): https://www.x.com/sherveenWhat we learn on this episode...Childcare Hiring: Traditional job boards and agencies haven’t caught up to modern families—or the caregivers who do the real work. Hear how a founder spent 12 years as a nanny in NYC, building a new, more personal approach to matching.Sports Venue Modernization: Bookings, replays, in-venue experiences: replacing labor costs with software can transform margins and user delight. But how do you convince legacy clubs and fitness centers to “modernize”?Real Pitch Advice for Marketplaces: Whether targeting busy parents, club owners, or any unsexy vertical, see how clarity about who pays, why they pay, and how you’re different can make or break a venture.Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.In a Job Search?Explore our newest channel for 2025’s ultra-competitive talent landscape:https://youtu.be/dlbfZJmY8t8Thank you to these intrepid founders for stepping into the spotlight. The Feedback Loop is here to help refine your pitch, sharpen your go-to-market, and share battle-tested investor perspectives. Make sure to subscribe for more real-time, no-nonsense feedback on how to pitch your startup.Disclaimer: This content is for educational purposes only and does not constitute investment advice. Always do your own research before making any investment decision.Amina Sako, founder of Karama: https://www.linkedin.com/in/amina-sako-a12782141Ben Borton, co-founder of PodPlay Technologies: https://www.linkedin.com/in/bortonDrop a comment – feedback is the lifeblood of builders everywhere!
  • 65. AI-Enabled Meditation & B2B Data Management

    27:26||Season 1, Ep. 65
    How do startup investors really evaluate founders and their pitches? What's truly required to raise a seed round or a Series A?On this episode of The Feedback Loop, we hear from 2 startup founders building the future and from 2 venture investors offering them feedback on their concept and storytelling – live, candid, and unfiltered!One founder is building a secure data platform for businesses to store, share, and collect repetitive information, and another is building an AI-powered meditation companion.It’s time for Episode 064 of The Feedback Loop!Each founder has 1 minute to pitch. Then, they get feedback from two check-writing venture capitalists – feedback to push them forward in their early stage storytelling journey. Because even the best of founders can be held back from their ability to pitch their business, to tell a story that is compelling but not complete.That feedback comes from our host, Sherveen Mashayekhi, founder and CEO of venture-backed Free Agency. He's also an angel investor and an LP in multiple venture funds. Each week, he's joined by a rotating seat featuring a guest venture investor, and this week, that's...Guest Investor: Lauren Reeves​Lauren Reeves is an Investor at MGV, an early stage SaaS fund based in SF and NYC. She also leads the team's east coast startup ecosystem initiatives. She brings a unique technical background to the judges' table — having previously been a software engineer building in AI, ML, and at notable companies like BlackRock, Postmates, and Alto Pharmacy.Follow Lauren on LinkedIn: https://www.linkedin.com/in/lauren-a-reevesFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmFollow Sherveen on X (Twitter): https://www.x.com/sherveenWhat You’ll Learn in This EpisodeMaking “Unsexy” B2B Tech CompellingA data-sharing solution for financial institutions can feel dry. You must reveal how it saves time, reduces errors, or eliminates friction for thousands of businesses.Differentiating in a Crowded Meditation MarketApps like Calm & Headspace have huge brand power. Show precisely why your approach (calendar sync, AI buddy, social groups) solves the “drop-off” problem in a new, sticky way.Highlighting Real User JourneysIn regulated or consumer-wellness spaces, point to specific workflows to bring the product to life – from compliance crises at banks to how and why users commit to a meditation routine.Why This Team?If you’re an ex-banker connecting Zelle & Venmo, or an ex-engineer building mindful apps, clarify how your domain expertise cements credibility, and how your daily vantage point revealed the solution.Addressing Investor SkepticismFounders must disarm the “Is it too trivial?” or “Aren’t there 100 others?” questions. Show market tailwinds, user data, or urgent pain that turns your product from a nice-to-have into a must-have.Want to Pitch Your Startup Live?Apply now at afterfeedback.com and join our growing community of founders and investors.Thank you to these intrepid founders for stepping into the spotlight. The Feedback Loop is here to help refine your pitch, sharpen your go-to-market, and share battle-tested investor perspectives. Make sure to subscribe for more real-time, no-nonsense feedback on how to pitch your startup.Kathryn Outlaw is the co-founder of Spheros: https://www.linkedin.com/in/kathrynoutlawJeremy Yencer is the co-founder of Mindful Buddy: https://www.linkedin.com/in/jeremyyencerDisclaimer: This content is for educational purposes only and does not constitute investment advice. Always do your own research before making any investment decision.