Funds and Founders: Untold Journeys Behind Their Breakthroughs

How do you actually sell to enterprises? Why do most startups fail at it? In this episode, we talk to the founder of DataColor.ai — a serial entrepreneur who built and sold his last company and is now building in the enterprise AI space. We dive deep into how enterprise sales really work, how to tap into communities for feedback, and the mindset shift between your first and second startup.💡 Learn about:Enterprise sales psychologyHow to build with feedback loopsWhat most founders get wrong about VC moneyHow second-time founders think differentlyTimestamps:00:00 – Intro: From Bing to DataColor.ai01:15 – What is DataColor.ai building?02:00 – Role of community for startup founders04:00 – How to extract value from founder communities06:00 – The real way to reach out cold (and get replies)08:50 – What excites him about AI in enterprise10:30 – The real enterprise AI opportunity12:15 – What a Chief Data Officer really does13:30 – Selling to enterprise vs SMBs – explained with a car analogy15:00 – Why product matters the least in enterprise sales17:00 – Should startups even try selling to enterprise?19:00 – Smart marketing and how to build trust early21:00 – Second-time founder mindset: What he’s doing differently24:00 – The startup trap: Solving tomorrow’s problem today26:00 – Fundraising strategy: Not all money is equal29:00 – Should you avoid VCs early on?32:00 – Real stories: Founders who raised too soon34:00 – Why he chose strategic angels only37:00 – Is cap table dilution really a problem?39:00 – What’s holding back growth today?40:00 – Favorite tools, tech stack & startup habits41:00 – His big lesson from the first startup42:00 – The question every founder should answer

What happens when a startup sales pro burns out and decides to start a podcast? In this episode of Funds and Founders, we sit down with Pat Killoren — host of Lone Startups who shares his wild journey from scaling beer brands and influencer platforms to building community-led content in Austin.🎙 We go deep into:Building sales teams as a founderThe mistakes startups make in GTM strategyBurnout, pivots, and personal reinventionHow to monetize podcasts through real partnerships (not just ads)Whether you're a builder, creator, or investor, this episode will leave you with tangible lessons on growth, niche branding, and sustainable success.TIMESTAMPS:00:00 – Intro: Who is Pat Callaghan?01:00 – Why he chose Austin and non-tech founders03:30 – His journey from beer to blockchain06:00 – What is Go-To-Market ?08:00 – The Enterprise Trap: Why startups jump too soon10:00 – How scrappy founders should build sales14:30 – Why you shouldn’t send proposals too early16:00 – How founders waste time chasing the wrong customers18:00 – Picking the right channels: The Web3 sales story21:00 – Cold outreach vs sniper sales: What works today23:00 – How to hire your first sales hire (without getting burned)25:00 – Why he quit sales and started a podcast28:00 – The admin pain of podcasting no one talks about30:00 – The monetization struggle: why brands hesitate32:00 – Seasons vs weekly: how he’s structuring Lone Startups36:00 – Format talk: from nature podcasts to 3D LED sets40:00 – Roundtable format: a future idea for deep-dive episodes44:00 – The mental blocks of podcast production quality46:00 – Tools + Tech Stack for running the show52:00 – Why video editing has become his new obsession54:00 – Question for the next guest56:00 – Where to follow Pat & closing thoughts

In this episode of Funds and Founders, we sit down with Andrew Ackerman, a seasoned founder, venture studio operator, and author of The Entrepreneur’s Odyssey. Andrew shares real, gritty stories from his journey building startups, transitioning into VC, launching a venture studio, and why he decided to write a novel-style business book that actually teaches while entertaining. He breaks down the harsh truths of buyouts, mistakes first-time founders make, the fundraising game, and the one question every VC is silently asking—why now?If you're a first-time founder, a startup dreamer, or someone trying to raise your first round—this episode might just save you years of pain.Watch the full episode on  @FundsAndFounders  Timestamps00:00 - Intro to Why Andrew wrote The Entrepreneur’s Odyssey01:15 - The "Goal" book inspiration & startup storytelling01:59 - How Andrew actually wrote the book04:11 - Using GenAI for book marketing 08:10 - Prompt engineering and AI frustration10:56 - Andrew’s unfiltered startup journey15:00 - The myth of glamorous exits20:00 - Behind-the-scenes of sourcing Facebook stock24:15 - Portfolio performance and founder expectations26:27 - Fundraising truth bombs & understanding VC incentives28:00 - How VCs actually evaluate founders30:20 - What Andrew is up to now & why construction tech excites him32:00 - Thoughts on building standout VC firms33:30 - The #1 question VCs ask: Why now?35:05 - Should you build a better version of a mediocre product?38:00 - Who the book is really for (first-time founders & their moms!)39:13 - Fundraising advice for first-time founders41:00 - Why cold emailing VCs doesn’t work42:30 - How to actually do VC outreach the right way47:00 - Final thoughts + how to reach Andrew49:10 - Why most business books suck (and how Andrew wrote differently)50:16 - Bonus: Get access to his startup masterclasses54:06 - Closing words from Andrew#vcfunding #podcast #startup #business #entrepreneur #invest #funding

In this episode of Funds and Founders, we sit down with the co-founder and CEO of FletchPMM—a company that’s helped over 350+ B2B startups fix their biggest problem: nailing positioning and messaging.We go deep into:The $1.5M journey in just 20 monthsWhat most B2B startups get wrong about value propsWhy building distribution first beats productThe real meaning of product-market fitHow to use LinkedIn to grow a 7-figure businessWhether you're bootstrapping or venture-backed, this is the episode every founder needs to hear.Timestamps:00:00 – Intro & Plug: What FletchPM does01:13 – LinkedIn as a distribution channel02:02 – The guest’s entrepreneurial journey03:14 – Origin story of FletchPM & the meaning behind the name05:30 – What is a value proposition?06:48 – Common mistakes B2B founders make10:24 – Specificity vs Scale: The 80/20 of niche selection12:06 – The importance of consistency in marketing14:33 – Distribution > Product16:47 – Building a founder brand18:09 – Lessons from being a generalist23:08 – How often should startups revisit positioning?25:13 – What is product-market fit really?27:00 – Go-to-market fit vs solution fit30:36 – DIY positioning: When & how to run the exercise32:16 – Why founders should think like marketers34:06 – Leaving a 9-5 to build a consultancy36:06 – How the co-founders met and got specific39:14 – Building distribution through a niche market map43:52 – Co-founder dynamics & communication styles46:03 – Decision-making heuristics50:35 – Competitive positioning done right52:12 – Leaving the agency & scaling up54:12 – The 3 paths they considered after early success56:48 – How the positioning evolved over time59:00 – Pricing journey: From $300 to $10K1:01:59 – What clients really get out of working with them1:05:20 – Founders can't outsource their thinking1:07:40 – Building a 7-figure business through LinkedIn1:10:14 – Tips for writing better LinkedIn content1:12:49 – Authenticity vs persona1:14:11 – Best time to post on LinkedIn?1:18:05 – 3 must-have resources for B2B founders1:19:10 – FletchPM's tech stack1:20:21 – What keeps him up at night1:21:07 – One question for the next guest1:22:03 – Final plugs & where to reach out

In this episode, we sit down with the founder of TrulyMadly, India's most trusted dating app, to explore the startup journey, fundraising pitfalls, growth hacks, and how TrulyMadly is solving the trust problem in Indian online dating.We dive deep into:- Competing with global giants like Tinder and Bumble.- How compatibility scores and trust-based algorithms changed the game.- The dark side of fake profiles and how TrulyMadly tackled it.- Fundraising regrets and the decision to stay profitable.- Building a brand people actually trust in a highly sensitive market.Whether you’re a founder, product builder, or just curious about the business of love.This episode is packed with insights. Watch the full episode on  @FundsAndFounders  Timestamps:00:00 - Intro01:23 - The European backpacking trip that changed everything03:39 - Early career: From payments to dating06:35 - Building a product for Indian singles09:03 - How TrulyMadly started12:10 - Solving the dating trust problem in India15:12 - TrulyMadly vs Tinder: What makes us different17:30 - Revenue vs Users: The real startup pivot20:02 - Fundraising mistakes & hard lessons22:25 - Branding, logo, and product-market fit25:47 - Compatibility scoring & TrulyMadly algorithm28:10 - Marriage success stories from TrulyMadly30:17 - Why TrulyMadly charges users (and why it works)33:50 - Dealing with fake reviews and app store ratings36:04 - The importance of frugal innovation39:00 - Final thoughts, rapid fire & what’s next

In this episode, we dive deep into a candid conversation with a founder who shares how he stumbled into consulting, earned a year's salary in a single month, and built impactful startups straight out of college. From building websites for the price of a cigarette to launching mobile products before the smartphone wave, this is a raw and relatable story for every aspiring entrepreneur and product builder. 🚀 Watch the full episode@FundsAndFoundersSnehil shares:Accidental path to consultingLessons from early startup hustleBuilding in college with zero backupLaunching India's first e-commerce mobile appConviction-led product building in the matrimony spaceTimestamps: 00:00:01 – Introduction to the Guest 00:20:10 – Earning a year’s salary in one month 00:21:10 – How I accidentally became a consultant 00:23:52 – Building websites during college 00:28:41 – Balancing college with side hustles 00:33:23 – Inspiration from "Pirates of Silicon Valley" 00:40:04 – Realizing the power of getting businesses online 00:44:49 – Building India's first mobile e-commerce site 00:50:00 – Why service businesses can hold you back 00:55:06 – Building trust in online matrimony platforms#ecommerce #consultant #business #entrepreneur #podcast #entrepreneurship #startup #webdevelopment #siliconvalley #productdevelopment

How I Hacked College Admissions to get Into Top schools!descriptionIn this episode of Fundsandfounders, we sit down with Anthony Berryhill, the founder of Elite College Hacker, to discuss the insider secrets of elite college admissions. Anthony shares his personal journey from growing up in New Orleans' Lower Ninth Ward to getting into Stanford and Yale, and how he now helps students from diverse backgrounds navigate the college admissions process.🔹 How do top schools really choose applicants?🔹 What are the biggest mistakes students make in their applications?🔹 How is AI and tech changing the admissions industry?🔹 How can students stand out beyond grades and test scores?If you’re a student, parent, or entrepreneur looking to understand the evolving landscape of college admissions, this episode is packed with insights, strategies, and practical advice.**** Timestamps:📌 00:00 - Intro to the episode📌 00:14 - Meet Anthony Berryhill & his company Elite College Hacker📌 01:10 - How Anthony’s journey started: From at-risk youth to Ivy League success📌 02:55 - The school-to-prison pipeline & how he escaped it📌 06:06 - The power of debate & how it changed his life📌 09:11 - What top schools REALLY look for in applicants📌 14:39 - The biggest mistakes students make in applications📌 20:44 - How he built Elite College Hacker from a side hustle to a business📌 25:24 - Is college still worth it? How the industry is changing📌 32:36 - How students can stand out in Ivy League admissions📌 39:50 - The red flags when hiring a college admissions consultant📌 48:56 - Where the real opportunities are in the college admissions industry📌 58:04 - The best resources for college admissions success📌 1:06:37 - Final thoughts & how to reach out to AnthonyConnect with Anthony: 📧 Email: Anthony@elitecollegehacker.com🌐 Website: www.elitecollegehacker.com📱 LinkedIn: Anthony Berryhill🔔 **Subscribe @fundsandfounders for more insights on entrepreneurship, funding, and business success!#CollegeAdmissions #EliteSchools #Stanford #Yale #IvyLeague #Entrepreneurship #AdmissionsConsulting #Fundsandfounders**

In this episode of Funds & Founders, we sit down with Ansh, co-founder of Quickreel, the AI-driven platform that helps content creators, brands, and marketers transform long-form videos into viral short-form clips.We dive deep into his entrepreneurial journey — from selling stickers in second grade to building a SaaS product with over 100K users. He shares his growth mindset, the ups and downs of building a startup, fundraising stories, and how Quickly stands out in the crowded content creation space.Ansh shares:💡 The inception of Quickreel and solving real creator problems💰 The grind of early-stage fundraising and finding the right investors🎯 Scaling from 0 to 100K+ users with minimal marketing⚡ The challenges of building in the creator economy📊 Pricing strategies, customer acquisition, and competition insightsIf you're a founder, content creator, or just love stories of building from scratch — this one's for you! Watch the full episode⏰ Timestamps:00:00 - Intro & Guest Introduction01:05 - What is Quickreel? Solving the short-form content problem02:30 - Early entrepreneurial spark: Selling stickers in 2nd grade05:00 - Choosing tech over family business08:15 - The idea behind Quickly: From agency work to product building11:45 - First MVP struggles and user feedback14:30 - Acquiring the first 500 users without ads17:20 - Fundraising journey: From self-funding to investor backing21:00 - Pricing strategies: Moving from free to paid users25:45 - Competing with Opus Clip & other clip generators29:40 - Balancing profitability vs. user growth33:00 - The future of AI in video editing36:15 - Expansion plans: APIs, agencies, and scaling globally40:00 - Rapid Fire Round: Tech stack, marketing tools & resources42:30 - Biggest startup challenges & what's next for Quickly44:20 - Advice for First-Time Founders46:00 - Question for the Next Guest

**From delivering newspapers in 4th grade to raising millions for real estate and co-founding a thriving co-working space—James Wahba’s journey is nothing short of inspiring.**🚀In this episode of Funds & Founders, James shares:✅ How his childhood paper route taught him business fundamentals 📈✅ Raising $13M at 25 for real estate development 🏗️✅ Building one of NYC’s most iconic co-working spaces 🚀✅ Lessons from working alongside startups like Uber, Instacart, Stripe, Airbnb✅ Why co-founder conflicts are one of the biggest startup killers 😨If you’re an aspiring entrepreneur, real estate investor, or startup founder, you don’t want to miss this one!Timestamps:00:00 - Welcome to Funds & Founders!00:20 - James Waba’s entrepreneurial journey begins01:14 - Growing up in Connecticut and learning business from a paper route02:18 - The business lessons from his first job 📜03:14 - Learning about customer retention and revenue at a young age05:10 - From paper route to film school & shooting concerts 🎥06:35 - Starting one of the first online streaming sites (before YouTube!)07:54 - Partnering with Microsoft & early struggles of internet startups 💻09:12 - Raising funds & the early days of NYC tech12:22 - Competing in the pre-YouTube era—how streaming was built back then16:04 - Shutting down the startup and pivoting to real estate development17:08 - Converting industrial property to high-value waterfront real estate19:52 - Raising $13M for a real estate project at 2522:11 - The 2008 market crash hits—what happened next?25:46 - Lessons learned: How to survive market crashes28:49 - Bootstrapping vs. raising VC: What should startups do?31:07 - The reality of investor expectations & startup funding32:55 - Pivoting from real estate to co-working spaces 🏢35:49 - How James built one of NYC’s top co-working spaces39:32 - Uber, Instacart, and Airbnb worked here—what was it like?41:14 - Why taking equity over cash would have been the best move44:08 - The rise and fall of the co-working space model46:50 - How to build a real, engaged community (not just a Slack group)49:21 - Challenges of managing a co-working space & scaling it51:34 - What James is building in Austin & his new boutique hotel project54:45 - Rapid fire Q&A: Advice for founders, resources, and more58:07 - Best books for entrepreneurs 📚1:00:39 - What’s missing in the Austin startup ecosystem?1:01:34 - Final thoughts & where to connect with James

In this episode of Funds and Founders, we sit down with Rajesh Sawhney—a seasoned investor, advisor, and the founder & CEO of GSF—who’s backed over 135 companies. Rajesh shares deep insights on what first-time founders need to know, the art of achieving product–market fit, and the unique dynamics of the Indian startup ecosystem. Whether you’re just starting out or already deep in your entrepreneurial journey, Rajesh’s practical advice on early validation, team building, and strategic execution is invaluable.Learn how Rajesh:Evaluates startup potential by spotting early traction and customer validationDetermines the right stage to raise funds and scale a businessSupports founders through hands-on mentorship and strategic guidanceNavigates the differences between local and global startup ecosystemsAdapts his investment approach in a rapidly evolving tech landscapeTimestamps: 0:00 – Introduction: Meet Rajesh Vijay and his journey as an investor and founder9:10 – From Idea to Product: How early validation sets the stage for success19:50 – Tips for First-Time Founders: Balancing passion with pragmatic execution27:45 – Understanding Product–Market Fit: Recognizing early indicators and challenges41:24 – Funding Stages: The importance of small validations before big bets51:20 – Evaluating Founders: Key traits like decision-making, team building, and adaptability63:10 – The Role of Angel Investors: Mentorship and strategic support for startups76:50 – The Indian Startup Ecosystem: Regional insights and the nuances of market dynamics87:30 – Regulatory Impact: Adapting to policy changes for sustainable growth95:45 – Final Thoughts: Embracing a long-term vision in an ever-changing landscape