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

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