PODCAST · business
The Sherveen Show
by Sherveen Mashayekhi
Where we discuss the intersection of startups, tech, business, and society.I'm always interested in connecting two disparate stories, tying together unobvious trends, and paying attention to different communities. I'm not here to give you a scoop on the news, but instead to share a take, mine or someone else's. Because when we understand how things work, we can move with far more intention.And by the way, I'm Sherveen, the founder and CEO of venture-backed Free Agency. I'm also an occasional angel investor and host of two other shows + podcasts. More than anything, I'm a nuance guy.Sometimes, it'll be takes on the news. Other times, deep dives on evergreen topics. Sometimes, it'll just be me talking to you, and other times, it'll be conversations with startup founders, tech CEOs, academics, subject matter experts, and influencers. Always trying to connect the dots.Twice a week. Hosted on Aca
-
25
Better Accounting = $$ = Growth (Daniel of Bags)
Secure those bags! Let's dive deep into the wild world of financial management and small-business growth! It isn't just about traditional accounting and capital, but the reasons why...- Every small business owner hates their accountant- Black, Latino, and immigrant-owned businesses outperform in profitability- The changing landscape of venture-backed versus bootstrapped businessesIt's time for Episode 025 of The Sherveen Show!Featuring Daniel Taylor, co-founder and CEO of Bags, a financial growth platform helping businesses manage their finance and fund their growth with good debt.Follow Daniel on LinkedIn: https://www.linkedin.com/in/daniel-taylor-95973662Secure those Bags! https://securebags.comFollow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmWe get into:How accounting firms for small businesses often fall short, leaving founders with a hot mess come tax season.Bags's pivot, going from purely lending to a full-fledged “financial growth platform” that manages your books, secures funding, and strategically deploys working capital.Capital access as a forcing function: the ways in which a business's books can either help or hurt in the moment in which they need more cash to grow.Overlooked communities & their underestimated ROI: how Black, Latino, and immigrant-owned businesses often outperform in profitability – yet lack consistent credit access. TLDR: Bags is proving that inclusion is good business.Why Bench collapsed, and the story it tells us about the missed opportunity to serve the long-tail (and how venture capital is now trying to fill that gap).Building tech-enabled services: why manually helping customers at first can be the fastest route to real product insights and AI-driven scale.From figuring out the perfect domain to raising capital (or just being profitable from day one!), we cover all the ways founders can ditch boring old spreadsheets and finally start making data-driven decisions.Join us for more unfiltered founder stories every week, and subscribe to catch all the ways innovators are reshaping the future – one bold idea at a time. Hosted on Acast. See acast.com/privacy for more information.
-
24
AI Agents Learn to Talk and Shopify CEO Issues AI Ultimatum to Staff
What's the big deal with Google's Agent2Agent announcement? Why are so many new founders choosing not to raise $$ and avoiding co-founders? What's the deal with RESURRECTING DIRE WOLVES!?Welcome to Episode 024 of The Sherveen Show. :)In this episode...Google’s AI Announcements:Gemini suite updates, TPU breakthroughs, their Veo 2 video model... but everyone else is covering these updates, so let's focus on their new Agent2Agent (A2A) protocol and how it's going to supercharge cross-platform AI agent workflows. Plus, why their seemingly trivial Audio Overviews feature coming to Google Docs might be the biggest AI-driven consumer behavior modifier in 2025.Anthropic’s Claude Max:Claude’s new subscription tiers – testing whether users will pony up $100 or even $200 for access beyond usage limits... are they actually building something comparable to OpenAI's ChatGPT Pro ($200/mo), and where is AI pricing going next?Shopify’s Internal Memo:Leaked! But then said aloud. Tobi Lütke tells his team it's time to get on the AI train, and they'll even be judged for it in their performance review. Are we entering a “no headcount without AI” era?Dire Wolves Revived:Colossal Biosciences resurrects a 10,000-year-old species, hinting at future conservation (or Jurassic Park) possibilities. How cute is this!?Founders Going Solo (in more ways than one):New data from Carta shows a surprising number of tracked startups have just one founder and no VC funding. Venture capital got so popular over the past decade, so... what's the deal?Supercharged Image Generation:Midjourney v7 and OpenAI’s 4o Image Generation innovation is pushing AI generated visuals to completely new heights. Marketers and business owners can now spin out polished ads in minutes – but are the hands good enough yet?Key ThemesAI Agents & Automation: A wave of next-gen interoperability is here, promising less friction across platforms – if teams adopt new standards quickly.Enterprise AI Adoption: Memos from CEOs like Shopify’s Toby Lutke show how companies are demanding AI-first mindsets at every level.Bootstrapping & Solo Founders: Growing data reveals a shift away from multi-founder, VC-led teams – AI is enabling “leaner, meaner” businesses.Edge Cases in Bioscience: Dire wolf de-extinction signals how frontier tech can resurrect species, with broader implications for conservation – and potential ethical dilemmas.Connect with SherveenFollow Sherveen on X: https://www.x.com/sherveenConnect on LinkedIn: https://www.linkedin.com/in/sherveenmEnjoyed the show? Leave a comment with your thoughts down below! :) Hosted on Acast. See acast.com/privacy for more information.
-
23
First Accounting Firm on Mars? (Cyrus of Haven)
Get ready for a deep dive into one of the most overlooked (yet crucial) parts of startup life: back-office finances. In this founder to founder fireside chat, Sherveen speaks with Cyrus Shirazi, CEO & Co-founder of Haven, a tech-enabled bookkeeping, tax prep, and tax credit platform for startups and entrepreneurs.Most CPA firms feel stuck in the past. Attempts to automate miss the human element in the moments that matter.Cyrus is taking a different approach: he and his team are building a tech-enabled solution to "put your finances on autopilot" while still prioritizing extreme orientation around customer experience – from rapid Slack responses to AI-driven automations that simplify a founder’s life.We unpack why software alone can’t solve the complexity of startup financials, the power of human-centered support for spiky moments like fundraising and budget planning, and how to do more with less (even if you’ve raised millions). If you’re curious about navigating tax credits, building a talent-dense team of “maniac” hires, or balancing profitability vs. growth, this conversation is a must-see.This is Episode 023 of The Sherveen Show!Follow Cyrus on X: https://x.com/Cyrus845Follow Cyrus on LinkedIn: https://www.linkedin.com/in/cy-m-sFollow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmIn this episode...Tax & Accounting Redefined: Why old-school CPAs fail on experience, and how Haven flips the script for digitally native startupsFounders vs. Finances: Critical “spiky moments” (fundraising, new hires, expansions) where a hands-on partner changes everythingBootstrapping Mindset: Why starting lean fosters creativity, control, and better long-term results – even if you ultimately raise VCAI as an Assistant, Not a Substitute: The hidden ways automation can free up CPAs to give more personal, high-touch supportTalent Density & ‘Hiring Divas’: Building a culture that prizes intellectual curiosity, rapid iteration, and problem ownershipJoin us for more unfiltered founder stories every week, and subscribe to catch all the ways innovators are reshaping the future – one bold idea at a time. Hosted on Acast. See acast.com/privacy for more information.
-
22
Building a Beverage Brand (Lily of Figlia)
Get ready for a candid chat about building a premium non-alcoholic beverage brand – without selling your soul to “growth at all costs.” In this startup founder fireside, Sherveen sits down with Lily Geiger, founder & CEO of Figlia, a mission-driven aperitivo company providing sophisticated alternatives to alcohol.From her personal journey and motivation to start the company, to cold-calling restaurants and personally handling distribution, Lily shares her journey toward creating Figlia’s flagship flavor and brand. And for those wondering after listening to this conversation: Figlia is now available in Whole Foods!Hear how she navigated formulation in the middle of COVID, managed packaging logistics from LA to NJ, and found a no-nonsense approach to balancing brand integrity, profitability, and real human connection. If you’re curious about direct outreach in CPG, the sober-curious trend, or what it takes to stand out in a crowded beverage market, this episode is for you!This is Episode 022 of The Sherveen Show!In This EpisodeMission-Driven: Lily’s personal story and pathway to starting the company, and how it shaped Figlia’s “no-alcohol analog” approachFormulating the Future of Drink: Balancing cost, shelf life, and taste for a new wave of mindful drinkersNavigating Supply Chain: Going from a scattered LA–NJ pipeline to a more efficient setup in Utah, and the trials and tribulations in betweenDTC vs. Wholesale: Why a direct outreach strategy (500+ accounts!) beat “waiting on a distributor," and the more recent changeSober-Curious Movement: Making a stylish, sophisticated product that resonates with both non-drinkers and casual drinkers alikeBootstrapping to Angels: Lily’s mindset around self-funding, strategic investors, and protecting brand integrityFollow Lily on LinkedIn: https://www.linkedin.com/in/lily-geiger-1735b011b/Follow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmJoin us for more unfiltered founder stories every week, and subscribe to catch all the ways innovators are reshaping the future – one bold idea at a time. Hosted on Acast. See acast.com/privacy for more information.
-
21
Solving Transit Deserts (Su of Dollaride)
Why do some communities get left behind by public transit - and how can startups fix it? Get ready for a deep dive into public-private partnerships, govtech, and how a mobility startup is tackling “transit deserts” across underserved communities.In this episode, Sherveen sits down with Su Sanni, co-founder and CEO of Dollaride, a mobility company building digital and physical infrastructure for community transit. It's a financial services, SaaS, and IoT platform for small private transit companies in NYC with the ultimate goal to bring clean transportation to underserved communities. They offer solutions like facilitated financing, tools for payments/rides/tracking, and data and insights to help these small biz owners scale in their communities.They've raised $12M from Elemental Impact, Everywhere Ventures, Prehype, and Backstage Capital, and are the recipient of a $10M New York Clean Transportation Prize facilitating their Clean Transit Access Program (CTAP) project in NYC. This is Episode 021 of The Sherveen Show!From Su’s family roots in New York’s dollar van ecosystem to securing major insurance + EV financing deals for small fleet owners, this conversation highlights how creative problem-solving - plus a healthy dose of patience - can reshape local transportation.If you’re curious about B2G sales, turning a complex social challenge into a scalable startup, or how policy and innovation collide, you’re in the right place!From the economics of transit to the power of government collaboration, this conversation is a masterclass in turning a local need into a scalable impact.In This Episode- Transit Gaps & Underserved Communities: How local entrepreneurs fill the void and why official agencies often lag behind- Dollar Vans & Jitneys: The global phenomenon of “informal transit” and how it can be a stepping stone for regulated services- B2G Sales & RFPs: Securing large contracts, dealing with red tape, and the importance of patience in government deals- Public-Private Partnerships: The role of insurance, EV adoption, and government-backed programs that help scale private-sector solutions- Venture vs. Other Funding: How Sue pivoted from traditional VC to impact investors, grants, and creative debt vehiclesFollow Su on LinkedIn: https://www.linkedin.com/in/sulaimansanniFollow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmJoin us twice weekly on The Sherveen Show for unfiltered conversations at the intersection of tech, startups, and society! If you’re into solving big social problems through innovation (or if you just love a good founder story), hit subscribe and let’s go. Hosted on Acast. See acast.com/privacy for more information.
-
20
The Truth About Grok 3, Humane’s Ai Pin Failure, and Venture Capital’s Political Betrayal
Episode 020 of The Sherveen Show takes on the latest in tech, startups, AI, and society –nothing is off-limits.This week, we’re digging into Elon Musk’s newly released Grok 3 model from xAI, dissecting the fate of Humane’s Ai Pin, and exposing how crypto power plays and political maneuvers shape our world. Get ready for unfiltered takes and some strong opinions!Stay ConnectedFollow Sherveen on X: https://www.x.com/sherveenConnect on LinkedIn: https://www.linkedin.com/in/sherveenmSome of the things we discuss:- Grok and LLM benchmarks, and how to think about claims that Elon has gotten here faster than OpenAI, Google, and other players- Humane being bought by HP, why its Ai Pin failed to deliver on the hype, and how it should've just been an "imagination agitating product"- The SEC dropping its case against Coinbase, and how we should think about technologists claiming "wins" that they bought- Amazon paying a billion dollars to get the rights to create new movies and TV shows in the James Bond franchise, and what this means for content- And... some politics to wrap things out! Hosted on Acast. See acast.com/privacy for more information.
-
19
Reinventing Omnichannel CX (Kait Stephens of Brij)
Get ready for a deep dive into the future of retail, e-commerce, and how brands can finally bridge that elusive gap between offline and online. In this conversation, Sherveen sits down with Kait Stephens, co-founder & CEO of Brij, a fast-growing platform that helps brands collect critical customer data and craft immersive experiences across every sales channel – whether that’s Amazon, big-box retail, or direct-to-consumer.This is Episode 019 of The Sherveen Show!From leveraging QR codes and sweepstakes, to powering product registrations and real-world brand activations, Kait explains how her team is disrupting legacy “point solutions” by building a single platform that unlocks omnichannel data and deeper customer relationships. You’ll hear how Brij landed major creator-led brands like Feastables (MrBeast’s snack empire) and Skullcandy, and why venture-backed consumer products – especially those selling through retail – now consider offline data a must-have. Whether you’re curious about influencer marketing, building a SaaS platform, or just how to break out of the direct-to-consumer bubble, this episode is for you.Follow Kait on LinkedIn: https://www.linkedin.com/in/kait-margraf-stephensFollow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmWe cover:Evolving Consumer Behavior: How the pandemic popularized QR codes, changing offline-to-online engagement foreverModern Omnichannel Strategy: Why D2C-only brands struggle to scale and how offline data solves the margin problemEnterprise Sales & Retail Partnerships: Convincing major retailers and brand buyers to share (and utilize) data in new waysSaaS Product Development: Moving from point solutions to a unifying “platform” approach that adapts to different industriesInfluencer-Backed Brands: The do’s and don’ts of building for creators with massive reachPrivate Equity to Startup: Kate’s personal journey, finding product-market fit, and becoming an “optimistic operator”Whether you’re a founder scaling a SaaS product, a CPG brand expanding into big-box retail, or just curious about bridging the online-offline divide, this episode is packed with insights on the next wave of commerce innovation. Subscribe for weekly conversations on tech, startups, business, and society – only on The Sherveen Show.Keywords: omnichannel commerce, CPG brand strategy, private equity to startup, influencer-led brands, QR codes, product registration, rebates & sweepstakes, e-commerce, brand data, offline-to-online, direct-to-consumer (D2C), retail distribution, marketing automation, SaaS platform, venture-backed startup, The Sherveen Show Hosted on Acast. See acast.com/privacy for more information.
-
18
Automating Adulthood with AI: RealWorld’s Genevieve Bellaire
Get ready for a fresh take on adulthood: the messy, ever-evolving set of tasks and life admin most of us wish someone else would just handle. In this episode, Sherveen sits down with Genevieve Bellaire, founder & CEO of RealWorld, an AI-powered platform that helps you organize everything from your health insurance and taxes to your TSA PreCheck and friends’ birthdays—all in one place. Think of it as your digital co-pilot for “adulting,” whether you’re figuring out health benefits at a new job or finally tackling that 401k rollover you’ve been putting off.From defining what “adulthood” even is in 2024, to harnessing generative AI for a membership-based consumer app, Genevieve shares why solving this multi-category problem requires a holistic approach that goes way beyond finance alone. They also get into hard-learned lessons on fundraising a “non-existent category,” building (and pivoting) a product in real time, and how the new wave of AI tools is suddenly making the impossible—“automating” big chunks of your life—feel entirely within reach.If you’ve ever scrambled to find a missing insurance card, juggle 10 different health apps, or wished you had a personal assistant for everything from your taxes to your dentist appointments, this conversation is for you.This is Episode 018 of The Sherveen Show!We cover:Emerging Adulthood: Why real adult responsibilities start at different ages for different people, and the growing “quarter-life crisis” trend.Creating a Category: Genevieve’s fundraising journey for an app that handles all of adulthood—from work and finance to health and “fun stuff.”AI & Automation: How generative AI, autonomous agents, and OCR have drastically accelerated RealWorld’s roadmap, making truly automated life management possible.Onboarding Challenges: Why even “15 minutes to upload your docs” can feel like a barrier—and how RealWorld is leveraging user behavior (and AI) to solve it.Consumer Behavior: Delaying marriage and homeownership, switching jobs every 18 months, and how these trends create even more complexity for 20- and 30-somethings.Membership & Monetization: Building a direct-to-consumer subscription product that aims to eventually be your single trusted vault for every important life document and reminder.Follow SherveenX (Twitter): https://www.x.com/sherveenLinkedIn: https://www.linkedin.com/in/sherveenmFollow GenevieveLinkedIn: https://www.linkedin.com/in/genevieve-bellaire-24736237In this episode…We explore the new frontier of AI-powered “life management” apps and what it really takes to unify everything—finances, healthcare, government paperwork, everyday errands—into one streamlined, user-friendly platform. You’ll hear hard-won founder insights on building trust with consumers, establishing brand credibility, and why success depends on owning the user’s context in a way ChatGPT alone can’t do. If you’re juggling endless to-do lists and dreaming of an automated, organized future, you don’t want to miss this conversation.Join us for in-depth talks with founders, investors, and innovators shaping how we live and work at the intersection of tech, startups, and society. Subscribe for more weekly insights on building companies that transform everyday life.Keywordsadulthood, adulting, RealWorld, Genevieve Bellaire, membership product, AI-powered platform, personal finance, health insurance, frequent flyer programs, automation, generative AI, OCR, user onboarding, product-market fit, venture capital, consumer SaaS, brand trust, user experience, The Sherveen Show Hosted on Acast. See acast.com/privacy for more information.
-
17
Ozempic Won't Fix Healthcare: A Startup Founder's Mission to Solve Obesity
Get ready for a raw, urgent conversation about fixing America’s broken healthcare system — starting with obesity care. In this episode, Sherveen sits down with Elina Onitskansky, founder & CEO of Ilant Health, a value-based care startup tackling the $1.7 trillion obesity crisis by combining AI-driven analytics, human-centered care teams, and a mission to slash systemic costs while saving lives.From battling stigma and bias in medicine to calling out “pill mill” startups hijacking GLP-1 drugs for quick profits, Ilana pulls no punches. She shares why most digital health models fail patients, how TikTok “diagnoses” are worsening healthcare inequity, and why Ilant's high-touch, human-first approach is proving that obesity treatment can extend lives and save employers, insurers, and taxpayers billions.From her personal journey through weight loss (incl. bariatric surgery and shame) to building a healthcare company that's challenging deep-rooted stigmas, Elina shares raw insights about what's broken in American healthcare — and how to fix it. (+, inside the GLP-1 gold rush and why 80% of users quit, and why "calories in, calories out" is dead).This is Episode 017 of The Sherveen Show!Follow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmFollow Elina: https://www.linkedin.com/in/elinaonitskanskyWe cover:- The GLP-1 Backlash: Why “miracle drug” startups are repeating the opioid crisis playbook — and how Ilant Health is flipping the script.- Bias in Healthcare: Why 70% of doctors still call patients with obesity “lazy” (and how Ilant's peer navigators are breaking the stigma).- Value-Based Care vs. “Pill Mills”: Why employers and insurers are dumping cash into AI nudges (spoiler: they don’t work) and betting on Ilant's outcomes-driven model.- TikTok’s Diagnosis Problem: How social media fuels misdiagnosis — and why “lived experience” is Ilant's secret weapon.- Obesity ≠ Willpower: The data proving diets fail and why laparoscopic surgery + personalized care teams drive 10X better outcomes.- VCs’ Healthcare Blindspot: Why Silicon Valley still funds “adversarial” startups gaming prior authorizations — and the metrics that won over Ilant's investors.It’s about: value-based care, obesity stigma, health equity, GLP-1 drugs like Ozempic, Medicaid/Medicare innovation, healthcare SaaS, AI in clinical analytics, employer health plans, digital health startups, and the future of chronic disease management.What's key:obesity care, healthtech, health equity, GLP-1 drugs, healthcare startups, chronic disease management, Medicaid innovation, employer health plans, AI in healthcare, telehealth, digital health, prior authorization, healthcare costs, social determinants of health, clinical analytics, peer support, healthtech SaaS, healthcare bias, venture capital in healthcare Hosted on Acast. See acast.com/privacy for more information.
-
16
OpenAI's agent, grifters on X, Substack strikes back
Today, we've got... OpenAI's browser agent, controversies surrounding Stargate, bad tweets by people who know better, and attention being all you need, both in AI and outside of it!It's time for Episode 016 of The Sherveen Show! If it's your first time, we wrestle with the intersection of startups, tech, business, and society. Let's connect the dots together.We cover:- OpenAI’s Operator: Why this early research release is one you should pay attention to, including a live preview.- Tech Meets Politics: Stargate, Trump, Sam Altman, and Elon Musk’s competing incentives - it's a mess to sort.- Instagram’s “Forced” Following Fiasco: Everyone put on their tinfoil hat for 24 hours there...- Substack’s $20M Creator Fund: A bold move to bring more creators into Substack’s ecosystem. We also connect the dots to Netflix’s gaming pivot and Instagram’s Reels bonuses.- Sherveen's grievances: Complaints about the WFH crowd, the All-In Pod and Chamath Palihapitiya, and a recommendation for a podcast to watch this weekend.If you’re fascinated by how AI innovation, political power plays, and creator monetization shape our world, this episode is a must-listen.All links and references:(coming later today)Follow me, maybe?X: https://www.x.com/sherveenLinkedIn: https://www.linkedin.com/in/sherveenmIn a job search? Check out our latest channel for next-level advice in 2025's competitive talent marketplace: https://youtu.be/dlbfZJmY8t8Subscribe, like, comment, and share it with a startup nerd friend! Hosted on Acast. See acast.com/privacy for more information.
-
15
Life After TikTok, OpenAI Funds the News, and AI Job Seekers v. AI Recruiters
In Episode 15 of The Sherveen Show, we dive deep into the intersection of tech, startups, business, and society with a jam-packed lineup of thought-provoking topics:Why is Mark Cuban's vision for a decentralized TikTok competitor potentially flawed? In this episode, we dive deep into why protocols like AT (powering BlueSky) might actually reduce innovation in social media, contrary to popular belief. Plus, we unpack why Reels and YouTube Shorts haven't truly captured TikTok's magic – it's not just about the algorithm.But that's just the beginning. We're exploring some massive moves in AI: OpenAI is literally funding local newsrooms through Axios (yes, really), and Google's teaming up with AP in what might be the biggest push for real-time AI yet. Plus, LinkedIn just dropped game-changing AI tools for both job seekers and recruiters, adding another fascinating layer to the ongoing AI arms race in hiring.- Mark Cuban’s Big Idea: Could a decentralized TikTok rival really compete with the social media giants? We explore the promise and pitfalls of building on the AT protocol—and why it might not be as revolutionary as it seems.- TikTok vs. Reels & Shorts: Why Instagram Reels and YouTube Shorts aren’t the natural successors to TikTok, despite their algorithmic efforts. We unpack the unique user dynamics driving TikTok’s staying power.- AI Arms Race: OpenAI, Google, and the ongoing battle for high-quality data. From local news investments to real-time media partnerships, discover how AI companies are shaping the future of information—and what it means for you.- Job Search in the AI Era: LinkedIn’s new tools for job seekers and recruiters promise smarter matches, but are we just fueling an endless AI-driven cycle? We discuss the challenges and opportunities ahead.- Game-Changing AI Research: New advancements in large language models, from Google's Titan memory modules to Sakana AI's self-adaptive transformers, could redefine how AI evolves.- Plus, a throwback to Hunter Walk’s prescient essay on the rise of tech as a power player and its struggles to adapt to newfound scrutiny.If you're fascinated by the future of social media, AI innovation, and the ways technology shapes our world, this episode is for you.Decentralized social media, Mark Cuban TikTok competitor, AT protocol, TikTok decentralization, OpenAI-Axios partnership, Google and The Associated Press, Gemini AI products, AI-powered news, AI training data, local journalism and AI, AI in media, social media innovation, TikTok vs Reels and Shorts, future of AI, large language models, tech innovation 2025, OpenAI newsrooms, Google Gemini, job search AI, recruiter AI, collective action. Hosted on Acast. See acast.com/privacy for more information.
-
14
DEI Is Good, Actually (Wissam of Tough Leaf)
Get ready for a spicy conversation about disrupting outdated construction practices, navigating diversity compliance requirements in government contracts, and building an innovative B2B marketplace. In this candid interview, Sherveen speaks with Wissam Akra, founder & CEO of Tough Leaf, about how his platform is transforming the way general contractors find and hire small, diverse, and minority-owned businesses for major public and private infrastructure projects.From tackling compliance headaches and navigating shifting political + DEI landscapes, to the nitty-gritty of building a SaaS marketplace that scrapes data from countless government databases, Wissam shares how Tough Leaf is removing barriers for subcontractors nationwide. The two also get into the thorny topic of union bosses resisting automation, the reality of tech adoption in construction, and why a capitalistic solution can still advance social good. If you’re curious about construction tech, compliance automation, or how startups can disrupt traditional industries, this discussion is for you.This is Episode 014 of The Sherveen Show!UNRELATED/RELATEDIn a job search in tech? You've seen Sherveen talking about the latest in business and society on The Sherveen Show, on stage giving startup founders feedback on The Feedback Loop, and having deep dive tech and foundership conversations on Three Course Founders...But he's also the founder/CEO of Free Agency and, since 2019, has helped hundreds of candidates in tech win over $400M in offers – he knows job search, and now you can learn it from him, too. For those in an active search (or who will be in the next 6 months), Breakthrough Job Search is a cohort-based course for tech industry professionals looking for an edge in this historically challenging job market. Enroll: https://www.freeagency.com/breakthroughFollow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmFollow Wissam: https://www.linkedin.com/in/mwakraWe cover:Union Bosses & Automation Backlash: Why some labor groups resist new technology and how it affects the U.S. economy.Construction Tech & SaaS Solutions: The 25-year-old methods that Tough Leaf is replacing with a data-driven, AI-matching approach.Navigating DEI & Compliance: How government mandates for small, women-owned, and minority-owned businesses create both challenges and opportunities.Public vs. Private Projects: The difference in compliance requirements and incentives for Amazon, Meta, and other large private players.Marketplace Pivots: Why the original “pure marketplace” model didn’t work—and how Tough Leaf found product-market fit with a more managed approach.Politics & Tech: How pendulum swings in public opinion, from Reagan to Trump, affect regulation, procurement, and DEI programs.Founder Insights: Balancing risk, trust-building, and pricing models (SaaS vs. outcomes-based) while trying to scale nationwide.It's about: construction tech, diversity in the tech and startup workforce, minority-owned businesses, tech adoption in a legacy industry, venture capital, artificial intelligence, and so much more. Hosted on Acast. See acast.com/privacy for more information.
-
13
YC-backed and Tackling Dementia (Nikhil of Craniometrix)
How do you combine machine learning, tech enabled services, and a scalable SaaS platform to improve outcomes in Alzheimer's and dementia care? In this episode, Sherveen Mashayekhi sits down with Nikhil Patel, the founder of Craniometrics, a cutting-edge healthtech startup backed by Y Combinator, Quiet Capital, Defy.vc, and others.From his early days at Y Combinator (YC) to building an AI-driven platform aligned with the Biden administration’s Medicare policies, Nikhil shares a journey of innovation, resilience, and a deeply personal connection to this mission.This conversation dives deep into what it really takes to build in healthcare:- The founding story of Craniometrics and Nikhil’s personal connection to dementia care- The decision to join YC, pivot early, and overcome the toughest startup challenges- How AI and machine learning predict care needs, empowering providers and caregivers- Navigating Medicare compliance, regulatory hurdles, and healthcare IT innovation- Lessons in fundraising, building with purpose, and scaling as a young founderAnd that's the conversation we have here on Episode 013 of The Sherveen Show!In this episode...We also explore the inside story of raising $6 million in funding, unpack why winning 51% of the time can be the key to startup success, and examine how the GUIDE program is changing dementia care in the United States. You’ll hear practical advice for aspiring entrepreneurs—especially those interested in healthtech and Y Combinator—as well as insights into what happens when big funding offers collide with the need to pivot toward a different product or market.We cover strategies for securing venture capital, aligning with Medicare’s GUIDE program, integrating machine learning, patient data, and provider workflows, and scaling go-to-market strategies for B2B healthcare products. Along the way, we look at how Craniometrics balances patient needs, caregiver support, and physician efficiency, building a brand that resonates with patients, families, and the broader healthcare community.Follow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmFollow Nikhil: https://www.linkedin.com/in/nikhil-s-patelThis conversation is packed with insights for startup founders, healthtech enthusiasts, and anyone navigating the intersection of technology, healthcare, and policy innovation. Whether you’re interested in building a mission-driven business, learning how to tackle regulatory challenges, or scaling a startup, this episode is for you.Join us for in-depth conversations with founders, investors, and innovators shaping the future of technology. Subscribe for weekly insights into building successful startups at their earliest of stages. The Sherveen Show is all about connecting the dots between tech, startups, business, and society.- Starting a healthcare startup and participating in Y Combinator (YC)- Pivoting from direct-to-consumer diagnostics to provider-focused dementia care- Integrating machine learning, patient data, and provider workflows- Strategies for securing venture capital and seed funding in healthcare- Balancing patient needs, caregiver support, and physician efficiency- Building a brand that resonates with patients, families, and the healthcare community Hosted on Acast. See acast.com/privacy for more information.
-
12
An Affair in a Storage Unit!? (Katharine of Stuf)
Sometimes, startups are about a magic moment where the right founder is staring at the right thing – in this case, empty, unused commercial real estate – realizes there's a different way to leverage that thing, that an arbitrage exists, that if you do just a few things differently, there's opportunity for everybody.And that's definitely the story with Stuf and Katharine Lau. Stuf is a next-generation self storage startup, and Katharine is its founder. Unlike the self storage solutions of yesterday, Stuf is reimagining how we think about space. It's tech-enabled and modern, but the best part is the business model innovation: she signs deals with commercial landlords who have unused space (nowadays, this is a lot of them!), then outfits these spaces to become a "home away from home for your stuff."For landlords, it's a monetization opportunity at a time when they could really use it. For consumers, it's a more modern storage experience – and it comes at a time when people are living in less than space than ever, want to put some of their stuff away, and want to access that stuff on-demand and at their leisure as an extension of their daily or weekly life.Stuf is bringing a new-age vibe to an old-school product. And that's the conversation we have here on Episode 012 of The Sherveen Show!We also talk about the nitty-gritty of convincing landlords to try something new, the challenges of building a team, and the surprising (and sometimes scandalous) things people store behind those metal doors.Whether you’re a curious founder, a real estate buff, or someone who just wants to know what goes into reinventing a simple concept, this episode is packed with insights. Stick around for an honest chat on raising VC money in a tough market, the importance of brand experience, and why staying focused matters — even when faced with endless opportunities.UNRELATED/RELATEDIn a job search in tech? You've seen Sherveen talking about the latest in business and society on The Sherveen Show, on stage giving startup founders feedback on The Feedback Loop, and having deep dive tech and foundership conversations on Three Course Founders...But he's also the founder/CEO of Free Agency and, since 2019, has helped hundreds of candidates in tech win over $400M in offers – he knows job search, and now you can learn it from him, too. For those in an active search (or who will be in the next 6 months), Breakthrough Job Search is a cohort-based course for tech industry professionals looking for an edge in this historically challenging job market. Enroll: https://www.freeagency.com/breakthroughFollow Sherveen on X: https://www.x.com/sherveenFollow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenmFollow Katharine: https://www.linkedin.com/in/katharinelau Hosted on Acast. See acast.com/privacy for more information.
-
11
Sustainability + Renewables but Make It Startup (Matthew of Relevate Power)
How can startup founders, tech builders, and private equity & venture investors build at the intersection of capitalism and community? What does it look like to align all the incentives in the right way, to take a profit driven approach to restoring waterpower dams while still benefitting and getting buy-in from local communities? If you want to hear about: the arbitrage opportunity with decaying energy infrastructure, how technology and automation can massively impact operational costs at satellite facilities, the nuances of financing & regulation that have left huge opportunities up for grabs in regional + local energy innovation, an engagement strategy that rewards local communities for their resources (even with a private equity archetype business model), and some of the nuances in between... this one's for you. Matthew Wenger went from building one of Canada's first fiber-to-home networks to leading billion-dollar hydropower projects on the Columbia River. Now, as CEO of Relevate Power, he's tackling one of clean energy's biggest challenges: making renewable power work 24/7 using facilities that have been neglected, abandoned, or underutilized. Over two decades, he's scaled multiple ventures from zero to hundreds of millions while keeping community impact at the core. A builder at heart with over $1B in infrastructure projects under his belt, Matt brings a rare mix of hard-tech experience and startup speed to the energy transition. This is Episode 011 of The Sherveen Show.Follow Sherveen: X: https://www.x.com/sherveen LinkedIn: https://www.linkedin.com/in/sherveenm Follow Matt: https://www.linkedin.com/in/mattwenger Hosted on Acast. See acast.com/privacy for more information.
-
10
Healthtech Pivot from B2C to B2B w/ Joseph of Circle
When you start a startup, there's pretty much one thing that's guaranteed: the roadmap you start with won't be the roadmap you scale with. When you're in that problem-solution-discovery phase as a founder, you know your mission as a founder, but you have to stay nimble to your method.And that was definitely the case for co-founder/CEO Joseph Schneier and the team at Circle, a healthtech company building a platform "designed to bridge the gap between benefit providers, health companies, and the communities they serve."But they got their start as Trusty Care, building a consumer product that offered plan comparisons for Medicare recipients, unbiased by any particular health insurer as a stakeholder. However, regulatory barriers held them back - but earned market insight into the systems at play meant two new open paths for Joseph: become a brokerage, or tackle deeper systemic and infrastructural issues plaguing the entire insurer, provider, and patient workflow.We cover all of that, and more, including customer feedback that led to their brand relaunch, social perception of health insurers, venture capital's reaction to Circle's approach, the AI opportunity, and incentives in slow-moving systems.This is Episode 010 of The Sherveen Show, featuring Joseph Schneier, co-founder and CEO of Circle (the healthcare one, not the fintech one).Follow Sherveen:X: https://www.x.com/sherveenLinkedIn: https://www.linkedin.com/in/sherveenmFollow Joseph: https://www.linkedin.com/in/joschneierIf you're interested in the early stage startup journey, incentives in healthcare, startup branding, social perception of insurance, venture capital and its relationship to healthtech, and everything in between, this episode's for you. Hosted on Acast. See acast.com/privacy for more information.
-
9
She's Building Gen Z's Favorite Money App (Katrin of Frich)
This startup founder understands Gen Z better than most and is tapping deep into their psychology to help them build better financial futures. It isn't just another fintech app that helps you budget or track your spending. Gen Z hates budgeting.Instead, Katrin Kaurov is building off of her own experience – she had to grow up fast, becoming financially independent early in her life as a model. And she had questions, but few places to turn to for answers. It's that moment that seems deeply centered at the root of her startup and consumer app, Frich, which is now one of the fastest growing Gen Z communities.We talk about: the dynamics of building for Gen Z, the relationship younger generations have to traditional financial institutions, the power of peer dynamics, the founder traits and resilience that might be underrated in the model community, Katrin's experience going through several startup accelerators, venture funding, and more.This is Episode 009 of The Sherveen Show, featuring Katrin Kaurov, Co-founder & CEO at Frich.Follow Sherveen on X: https://www.x.com/sherveenFollow Katrin: https://www.linkedin.com/in/katrin-kaurov-160972194If you're interested in startups, fintech, social finance, venture capital, underdog founder stories, female founders, early stage startup challenges, the rollercoaster of VC financing, and everything in between, this episode's for you. Hosted on Acast. See acast.com/privacy for more information.
-
8
Sustainable, DTC Period Care w/ Katie of Viv
She's a first time founder on a mission to better the lives of women and people with periods. The challenges, though, are endless: venture capitalists that don't empathize with the problem, embedded consumer habits and routines, massive legacy players taking shelf space, and so much more.But Katie Diasti might be the perfect person to take that all on. She's the Founder and CEO of Viv, an earth-friendly direct-to-consumer period brand, delivering period care to your door.And to build this business, she's had to do things like mess with her own biology for product testing and demonstrate how a menstrual cup works on a Zoom call with 20 male investors.In this conversation, we cover it all: the vision for Viv, how it got started, what it was like pitching feminine products to the male-dominated venture capital crowd, how she thinks about investors for her business, the challenges of this entrenched consumer space, how she's using TikTok to win, and so much more.This is Episode 008 of The Sherveen Show.Follow Sherveen on X: https://www.x.com/sherveenFollow Ankur: https://www.linkedin.com/in/katie-diasti Hosted on Acast. See acast.com/privacy for more information.
-
7
Sold Startup #1 for $250M, Now #2 w/ Ankur (Teachable, Carry)
Tune in to my conversation with Ankur Nagpal – he was the founder of Teachable, a creator-driven coaching and teaching platform which he sold for a reported $250M. Now, he's on to his second startup journey with Carry.Carry has raised a $10M Series A, led by Accomplice VC. Carry is an all-in-one tool designed to help business owners, financial advisors, tax professionals, and individuals manage their tax-saving accounts, investments, and financial plans in one place – centered around a novel solo 401k product.And today, we chat about Ankur's founder journey, including the hard moments in selling his first company, the earlier days of NYC tech, the lessons he's taking into building his second company, the stuff that's still hard as a veteran founder, and the nuances of building his product in the modern fintech landscape.This is Episode 007 of The Sherveen Show.Follow Sherveen on X: https://www.x.com/sherveenFollow Ankur: https://x.com/ankurnagpal Hosted on Acast. See acast.com/privacy for more information.
-
6
Character.ai Sued, OpenAI Worried re:AGI
Timestamps:00:00 - Hello!00:09 - Character.ai implicated in teen death05:19 - Chatbots that can flirt are addicting06:39 - OpenAI researcher says we're not ready06:26 - Anthropic lets AI control your computer!Relevant links:https://www.nytimes.com/2024/10/23/technology/characterai-lawsuit-teen-suicide.htmlhttps://www.washingtonpost.com/technology/2023/03/30/replika-ai-chatbot-update/https://blog.character.ai/community-safety-updates/https://techcrunch.com/2024/10/23/longtime-policy-researcher-miles-brundage-leaves-openai/https://milesbrundage.substack.com/p/why-im-leaving-openai-and-what-imhttps://www.anthropic.com/news/3-5-models-and-computer-usehttps://x.com/AnthropicAI/status/1848742761278611504 Hosted on Acast. See acast.com/privacy for more information.
-
5
Bootstrapped, Boozeless Beverage Business w/ Elizabeth Gascoigne
Tune in to my conversation with Elizabeth Gascoigne, Founder and CEO of Absence of Proof. It's a non-alcoholic event curation company, online bottle boutique, and beverage distributor, pushing the world's capability to have and enjoy boozeless experiences.Gen Z drinks an estimated 20% less per capita than their millennial counterparts (1). Since the 1970s, and especially from 2010 to 2020, we've seen massive declines in underage alcohol use (2) (3).There are more non-alcoholic bars, events, and pop-ups than ever. Companies like Kin Euphorics and Liquid Death are popularizing an "out loud" version of abstaining. And Absence of Proof is helping elevate non-alcoholic nightlife as an alternative to drinks-based norms.And today, we chat about Elizabeth's founder journey, the mechanics behind her many-business-model, bootstrapped business, her view on other non-alcoholic beverage companies, the demographics at play, how she views venture capital having not yet taken it on, and we even cover Andrew Huberman as it relates to a mission-driven founder staying aligned to their movement and zeitgeist. A fun conversation with a super compelling entrepreneur.This is Episode 005 of The Sherveen Show.Follow Sherveen on X: https://www.x.com/sherveenFollow Elizabeth: https://www.linkedin.com/in/elizabeth-gascoigne1: https://globalnews.ca/news/9411516/alcohol-consumption-decline-gen-z/2: https://pmc.ncbi.nlm.nih.gov/articles/PMC7612362/3: https://news.gallup.com/poll/509690/young-adults-drinking-less-prior-decades.aspx Hosted on Acast. See acast.com/privacy for more information.
-
4
Healthtech & Autoimmune Disease w/ Mette of Mymee
Tune in to my conversation with Mette Dyhrberg, Founder and CEO of Mymee. Mymee is a digital care platform designed to help individuals manage autoimmune diseases like arthritis, ankylosing spondylitis, lupus, and long COVID. They combine a mobile app, data analytics, and certified health coaches for their clinically-validated solution. They've raised a little over $15M from New York ventures, Half Court Ventures, and others.And today, we chat about Mette's founder journey, the challenges of and opportunities in dealing with autoimmune disease, how she views being insurer- and practitioner-friendly, her unique business model in healthtech, the debate between RCTs and personalized medicine, raising venture funding, and so much more.Timestamps:00:00 Introduction!00:45 Understanding Mymee's Mission02:47 Challenges in Autoimmune Healthcare04:23 The Mymee Method Explained05:51 Patient Experience and Journey10:22 The Role of Triggers in Autoimmune Diseases18:02 Innovative Business Model and Market Strategy22:22 Passion and Challenges in Healthtech25:06 The Rise of Behavioral Change Companies25:27 The Impact of COVID on Digital Health26:37 Personalized Medicine vs. Western Medicine28:46 Challenges in Medical Trials and Innovations33:21 Creative Solutions in Business and Medicine35:44 Startup Strategies and Team Building37:29 Patient Advocacy and Autoimmune Conditions45:29 The Future of Quantified Self and WellnessThis is Episode 004 of The Sherveen Show.Follow Sherveen on X: https://www.x.com/sherveenFollow Mette: https://x.com/metamette Hosted on Acast. See acast.com/privacy for more information.
-
3
VCs offering refunds; employees give up on equity
Timestamps:00:00 - Hello!00:27 - Tech imposes consequences01:58 - Upwork gets hit by AI03:56 - Layoffs in the video games industry08:16 - Employees giving up on startup equity11:37 - AI for job search is... bad?13:15 - Venture capital firms offering refunds15:52 - Women in tech sounding an alarm17:34 - You should listen to this podcast19:11 - Bye!Relevant links:https://x.com/varadhjain/status/1843080099916313056/photo/1https://x.com/emollick/status/1841929292021956712https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4527336https://x.com/ballmatthew/status/1843351557712293944https://www.matthewball.co/all/gaming2024https://www.linkedin.com/feed/update/urn:li:activity:7249138994670645250/https://x.com/rohanpaul_ai/status/1842712127556956230https://www.nytimes.com/2024/10/02/technology/crv-vc-fund-returning-money.htmlhttps://www.theinformation.com/articles/why-women-in-tech-are-sounding-an-alarmhttps://techcrunch.com/2024/10/07/vc-firm-nfx-laid-off-4-employees-and-plans-to-hire-more-investors/https://www.theverge.com/24260181/rabbit-r1-large-action-model-lam-playground-generative-ai-jesse-lyu-interview-users Hosted on Acast. See acast.com/privacy for more information.
-
2
Opportunities & Challenges in AI with Ravin T. of Credal (YC, Spark, Drive) | Ep. 002
Tune in to my conversation with Ravin Thambapillai, the co-founder and CEO of Credal.ai. They've raised about $5M (from YC, Spark Capital, Drive Capital) to build an AI application platform targeted at the enterprise. He's an Oxford graduate and Xoogler, and he and his co-founder (Jack Fischer) cut their teeth in the world of enterprise data security & AI at Palantir before starting Credal.And today, we chat about Ravin's founder journey, going through YC, his discovery of the Credal thesis, how he thinks about the frontier AI models and their integration into his product, building AI for the enterprise, and so much more. It's a wide-ranging conversation with someone making AI more practical for everyone else.00:00 Introductions00:39 What is Credal?05:26 From Palantir & COVID to Enterprise AI13:38 Navigating AI, Open Source, and Models17:24 Is OpenAI going to eat Perplexity?23:19 The Future of AI and Enterprise Integration24:17 The limits of foundational models27:46 Does Ravin recommend Y Combinator?31:13 Fundraising, venture capital, and the AI ecosystem33:09 Advice for AI startup founders36:00 Crowd Q&A49:40 Thanks, and bye!This is Episode 002 of The Sherveen Show.Follow Sherveen on X: https://www.x.com/sherveenFollow Ravin: https://x.com/ravin_tham Hosted on Acast. See acast.com/privacy for more information.
-
1
Automation backlash & content in the age of AI | Ep. 001
Episode 001 of The Sherveen Show! What the heck is The Sherveen Show? It's a new podcast where we'll be discussing the intersection of tech, startups, business, and society.I'm always interested in connecting two disparate stories, tying together unobvious trends, and paying attention to different communities. I'm not here to give you a scoop on the news, but instead to share a take, mine or someone else's. Because when we understand how things work, we can move with far more intention.And by the way, I'm Sherveen, the founder and CEO of venture-backed Free Agency. I'm also an occasional angel investor and host of two other shows + podcasts. More than anything, I'm a nuance guy.Sometimes, it'll be takes on the news. Other times, deep dives on evergreen topics. Sometimes, it'll just be me talking to you, and other times, it'll be conversations with startup founders, tech CEOs, academics, subject matter experts, and influencers. Always trying to connect the dots.Twice a week.And today, we're hitting two topics:- The dockworker strike and its relationship to other unions fighting automation- 3 types of content that are increasing in value in the age of AI, despite the oddsOkay, that's all for now. More soon. Subscribe. See ya. Hosted on Acast. See acast.com/privacy for more information.
We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.
No matches for "" in this podcast's transcripts.
No topics indexed yet for this podcast.
Loading reviews...
ABOUT THIS SHOW
Where we discuss the intersection of startups, tech, business, and society.I'm always interested in connecting two disparate stories, tying together unobvious trends, and paying attention to different communities. I'm not here to give you a scoop on the news, but instead to share a take, mine or someone else's. Because when we understand how things work, we can move with far more intention.And by the way, I'm Sherveen, the founder and CEO of venture-backed Free Agency. I'm also an occasional angel investor and host of two other shows + podcasts. More than anything, I'm a nuance guy.Sometimes, it'll be takes on the news. Other times, deep dives on evergreen topics. Sometimes, it'll just be me talking to you, and other times, it'll be conversations with startup founders, tech CEOs, academics, subject matter experts, and influencers. Always trying to connect the dots.Twice a week. Hosted on Aca
HOSTED BY
Sherveen Mashayekhi
CATEGORIES
Loading similar podcasts...