What drives a founder to go back into the grind after a life-changing exit?

In this episode, we sit down with Ganesh, a serial founder who bootstrapped his AI startup to millions in revenue, cracked the toughest enterprise clients like TCS and KPMG, and rebounded from losing 85% of revenue during COVID.

We cover:

- Why he didn’t raise VC early on

- Building an assessment company without asking a single question

- Selling into TCS, Indian Army & QSRs like Universal Studios

- Losing millions in revenue overnight and still surviving

- Exiting to a strategic buyer

- Why he's back in stealth mode building a sales AI company

Timestamps:

00:00 – Intro & how Ganesh and the host met

00:21 – Why build another startup after a successful exit?

01:06 – Spotting the opportunity with generative AI

02:12 – Cisco days & the shift to entrepreneurship

03:00 – Building culture at scale — the early inspiration

04:29 – From network optimization to people analytics

07:13 – Mistake: Building before validating

10:03 – First break via Plug and Play, no customers yet

11:08 – Breakthrough with DBS & positioning as a “cultural DNA” company

12:13 – Landing TCS, Byju’s, KPMG for large-scale assessments

13:25 – Pricing challenges in enterprise SaaS

18:15 – First funding — how Mitsubishi Ventures found them

20:32 – Crazy story of a 12-person Sunday 7AM investor meetingt

26:00 – QSR boom: Universal Studios, restaurant chains, & rapid growth

29:07 – COVID wiped out 85% of revenue overnight

33:00 – Why founder salaries matters even in bootstrapped companies

34:36 – Pivoting back to B2B — TCS saves the business

38:48 – Rebuilding revenue, landing Byju’s, scaling again

43:00 – Learn at Forbes, cultural learning styles, and the acquirer

46:32 – Post-exit reflections on taxes, dilution & what he’d do differently

51:10 – Starting again: the new stealth startup in AI Sales

57:00 – Early adopters welcome: Join Ganesh’s next journey

In this episode of Funds and Founders, we sit down with Michael, co-founder of Q Branch and Populace, who shares how he's helping international startups enter the U.S. and launching a fintech platform to fight financial inequality. From federal contracts and government culture to empowering underserved Americans through passive investing and discount networks, Michael breaks down the hard truths of money, persistence, and building in Austin.

What You’ll Learn:

- Why Most Startups Fail to Enter the U.S. Market

- The Broken Banking System and a Grassroots Fix

- Real Talk on Financial Literacy

- Startup Persistence & the 18-Month Grind

- What U.S. Founders Can Learn From International Builders

Timestamps:

00:00 - Intro & How They Met

00:30 - What Is Q Branch?

01:30 - Helping International Startups in the U.S.

02:10 - Government Contracts & Go-to-Market

03:20 - Populist: A Fintech for the 99%

05:00 - Breaking Down Financial Literacy

06:00 - How Populist Reverses the Bank Model

07:40 - Making Passive Investing Accessible

09:10 - Michael’s Entrepreneurship Origin Story

11:00 - Lessons From Federal Contracting

13:00 - How Q Branch Got Its First Deal

15:00 - Founder Persistence & Mentality

17:00 - Talking About Ideas Early

19:00 - U.S. vs International Founders

21:00 - Austin’s Startup Community

25:00 - Picking the Right Ecosystem

29:00 - Building Populace: From Idea to Launch

32:00 - Real Cost of Building a Fintech Startup

34:00 - Launch Strategy & What’s Next

35:00 - Final Advice for Founders

From building apps at Best Buy to getting into Techstars, this episode is a masterclass in startup grit. Our guest, a Toronto-based founder and ex-Apple/IBM engineer, walks us through building 35+ projects, what failed, what made money, how he learned sales from scratch, and why he’s now obsessed with solving go-to-market problems for B2B startups.

We go deep into:

- How to know when to kill an idea

- Lessons from making $0 to 5-figure MRR

- The truth about VC pressure vs bootstrapping

- Building SaaS + service hybrid models

- Staying sane while building solo

Timestamps:

00:00 - Intro: From On Deck to 35 Ideas

01:00 - Why most technical founders fail at sales

04:00 - Best Buy hack: Gaming ad revenue with Android apps

06:30 - First “real” win: Canada Top 10 apps

08:00 - Building “Spotify for News” (and shutting it down)

10:30 - When to kill your startup

13:00 - Side hustle to 1k MRR → quitting full-time job

16:00 - Why learning sales changed everything

18:00 - Selling blueberry honey to learn sales

21:00 - Cold email agency that failed — what went wrong

24:00 - SaaS vs. service models: What scales?

28:00 - “My platform did 10 things. Users wanted 1.”

31:00 - Mission-driven idea testing

35:00 - The 5K/month rule & building in public

38:00 - Should you raise VC or bootstrap?

41:00 - Burnout, support systems & staying sane

45:00 - AI tools stack: Cursor, Claude, Replit & more

50:00 - What actually keeps him going after 35+ tries

Cody Anderson is back for Part 2! In this episode, we dive deep into what actually works when it comes to go-to-market (GTM) strategies — especially for early-stage startups. Cody shares lessons from scaling Carta to $9B, building Tommy Homes, and advising multiple startups on GTM, brand building, and AI-led growth.

We cover:

- B2B vs B2C GTM approaches

- Why most startup advice is noise

- Personal brand vs company brand

- Building AI agents for sales, marketing & ops

- The future of one-person billion-dollar companies

🔗 Guest: [Cody Anderson](https://www.linkedin.com/in/codyanderson)

Timestamps:

00:00 – Cody's journey: From Carta to Tommy

01:48 – Why Cody’s GTM perspective is unique

03:38 – GTM strategies: B2B vs B2C

05:45 – The myth of "funnels" and what works now

08:16 – Tools, outbound, and unit economics

09:55 – Personal brand vs company brand

12:02 – How narrow should your ICP targeting be?

15:09 – B2C GTM: Channels, content & challenges

17:54 – Finding what works for you as a founder

20:16 – Shift to content is greater than followers (thanks TikTok)

23:13 – Niching down and the rise of shareable content

24:07 – Tommy Homes: Challenges in educating the market

26:34 – Building trust in a complex real estate model

28:49 – Services-as-Software: AI as the co-founder

31:05 – The one-person Slack-powered startup

34:00 – Why personal stories is effective than generic advice

38:18 – What’s next for Tommy

42:10 – Final advice: Ignore the noise, trust your path

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