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 psychology
• How to build with feedback loops
• What most founders get wrong about VC money
• How second-time founders think differently

Timestamps:

00:00 – Intro: From Bing to DataColor.ai

01:15 – What is DataColor.ai building?

02:00 – Role of community for startup founders

04:00 – How to extract value from founder communities

06:00 – The real way to reach out cold (and get replies)

08:50 – What excites him about AI in enterprise

10:30 – The real enterprise AI opportunity

12:15 – What a Chief Data Officer really does

13:30 – Selling to enterprise vs SMBs – explained with a car analogy

15:00 – Why product matters the least in enterprise sales

17:00 – Should startups even try selling to enterprise?

19:00 – Smart marketing and how to build trust early

21:00 – Second-time founder mindset: What he’s doing differently

24:00 – The startup trap: Solving tomorrow’s problem today

26:00 – Fundraising strategy: Not all money is equal

29:00 – Should you avoid VCs early on?

32:00 – Real stories: Founders who raised too soon

34:00 – Why he chose strategic angels only

37:00 – Is cap table dilution really a problem?

39:00 – What’s holding back growth today?

40:00 – Favorite tools, tech stack & startup habits

41:00 – His big lesson from the first startup

42:00 – 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 founder
• The mistakes startups make in GTM strategy
• Burnout, pivots, and personal reinvention
• How 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.

00:00 – Intro: Who is Pat Callaghan?

01:00 – Why he chose Austin and non-tech founders

03:30 – His journey from beer to blockchain

06:00 – What is Go-To-Market ?

08:00 – The Enterprise Trap: Why startups jump too soon

10:00 – How scrappy founders should build sales

14:30 – Why you shouldn’t send proposals too early

16:00 – How founders waste time chasing the wrong customers

18:00 – Picking the right channels: The Web3 sales story

21:00 – Cold outreach vs sniper sales: What works today

23:00 – How to hire your first sales hire (without getting burned)

25:00 – Why he quit sales and started a podcast

28:00 – The admin pain of podcasting no one talks about

30:00 – The monetization struggle: why brands hesitate

32:00 – Seasons vs weekly: how he’s structuring Lone Startups

36:00 – Format talk: from nature podcasts to 3D LED sets

40:00 – Roundtable format: a future idea for deep-dive episodes

44:00 – The mental blocks of podcast production quality

46:00 – Tools + Tech Stack for running the show

52:00 – Why video editing has become his new obsession

54:00 – Question for the next guest

56:00 – 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

Timestamps

00:00 - Intro to Why Andrew wrote The Entrepreneur’s Odyssey

01:15 - The "Goal" book inspiration & startup storytelling

01:59 - How Andrew actually wrote the book

04:11 - Using GenAI for book marketing

08:10 - Prompt engineering and AI frustration

10:56 - Andrew’s unfiltered startup journey

15:00 - The myth of glamorous exits

20:00 - Behind-the-scenes of sourcing Facebook stock

24:15 - Portfolio performance and founder expectations

26:27 - Fundraising truth bombs & understanding VC incentives

28:00 - How VCs actually evaluate founders

30:20 - What Andrew is up to now & why construction tech excites him

32:00 - Thoughts on building standout VC firms

33:30 - 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 founders

41:00 - Why cold emailing VCs doesn’t work

42:30 - How to actually do VC outreach the right way

47:00 - Final thoughts + how to reach Andrew

49:10 - Why most business books suck (and how Andrew wrote differently)

50:16 - Bonus: Get access to his startup masterclasses

54:06 - 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 months
• What most B2B startups get wrong about value props
• Why building distribution first beats product
• The real meaning of product-market fit
• How to use LinkedIn to grow a 7-figure business

Whether you're bootstrapping or venture-backed, this is the episode every founder needs to hear.

Timestamps:

00:00 – Intro & Plug: What FletchPM does

01:13 – LinkedIn as a distribution channel

02:02 – The guest’s entrepreneurial journey

03:14 – Origin story of FletchPM & the meaning behind the name

05:30 – What is a value proposition?

06:48 – Common mistakes B2B founders make

10:24 – Specificity vs Scale: The 80/20 of niche selection

12:06 – The importance of consistency in marketing

14:33 – Distribution > Product

16:47 – Building a founder brand

18:09 – Lessons from being a generalist

23:08 – How often should startups revisit positioning?

25:13 – What is product-market fit really?

27:00 – Go-to-market fit vs solution fit

30:36 – DIY positioning: When & how to run the exercise

32:16 – Why founders should think like marketers

34:06 – Leaving a 9-5 to build a consultancy

36:06 – How the co-founders met and got specific

39:14 – Building distribution through a niche market map

43:52 – Co-founder dynamics & communication styles

46:03 – Decision-making heuristics

50:35 – Competitive positioning done right

52:12 – Leaving the agency & scaling up

54:12 – The 3 paths they considered after early success

56:48 – How the positioning evolved over time

59:00 – Pricing journey: From $300 to $10K

1:01:59 – What clients really get out of working with them

1:05:20 – Founders can't outsource their thinking

1:07:40 – Building a 7-figure business through LinkedIn

1:10:14 – Tips for writing better LinkedIn content

1:12:49 – Authenticity vs persona

1:14:11 – Best time to post on LinkedIn?

1:18:05 – 3 must-have resources for B2B founders

1:19:10 – FletchPM's tech stack

1:20:21 – What keeps him up at night

1:21:07 – One question for the next guest

1:22:03 – 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 - Intro

01:23 - The European backpacking trip that changed everything

03:39 - Early career: From payments to dating

06:35 - Building a product for Indian singles

09:03 - How TrulyMadly started

12:10 - Solving the dating trust problem in India

15:12 - TrulyMadly vs Tinder: What makes us different

17:30 - Revenue vs Users: The real startup pivot

20:02 - Fundraising mistakes & hard lessons

22:25 - Branding, logo, and product-market fit

25:47 - Compatibility scoring & TrulyMadly algorithm

28:10 - Marriage success stories from TrulyMadly

30:17 - Why TrulyMadly charges users (and why it works)

33:50 - Dealing with fake reviews and app store ratings

36:04 - The importance of frugal innovation

39:00 - 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

@FundsAndFounders

Snehil shares:

• Accidental path to consulting
• Lessons from early startup hustle
• Building in college with zero backup
• Launching India's first e-commerce mobile app
• Conviction-led product building in the matrimony space

Timestamps: 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!

• description
• In 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 Anthony
• Connect 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 insights

If 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 Introduction

01:05 - What is Quickreel? Solving the short-form content problem

02:30 - Early entrepreneurial spark: Selling stickers in 2nd grade

05:00 - Choosing tech over family business

08:15 - The idea behind Quickly: From agency work to product building

11:45 - First MVP struggles and user feedback

14:30 - Acquiring the first 500 users without ads

17:20 - Fundraising journey: From self-funding to investor backing

21:00 - Pricing strategies: Moving from free to paid users

25:45 - Competing with Opus Clip & other clip generators

29:40 - Balancing profitability vs. user growth

33:00 - The future of AI in video editing

36:15 - Expansion plans: APIs, agencies, and scaling globally

40:00 - Rapid Fire Round: Tech stack, marketing tools & resources

42:30 - Biggest startup challenges & what's next for Quickly

44:20 - Advice for First-Time Founders

46:00 - Question for the Next Guest