Last month, we launched The VibeScaling Podcast.

The feedback so far has been positive, and man, it’s been fun filming this in person.

We plan to ship weekly (getting the kinks out with a new agency 🙂, sorry for my delay on ep 2), and you can expect the smartest GTM minds from the hottest companies to talk all things sales, AI, and startups.

Think of it as a baby born from two of my favorite podcasts - the content of 20VC (specifically their 20Sales series) meets the casual vibe of My First Million.

If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.

Some of our guests for Season One:

And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM on LI or reply to this email. We’ll keep openings rolling and be super open to suggestions of similar guests.

We film in-person in SF & NYC at top-notch podcast studios and have hired a post-production agency, so the quality will be high.

And now, onto the episode 🎙️

Shoutout to Kondo for sponsoring this episode of The VibeScaling Podcast.

Think of Kondo like “Superhuman for LinkedIn.”

It’s saved me countless hours with LI messaging, and you’d have to rip it from my cold, dead hands if you told me I couldn’t use it anymore.

Give them a try, and use this link to get 2 free months. No risk at all.

If you send a lot of LinkedIn messages, as I do, you won’t regret it.

I’ve known about Raph for a few years now, and I resonate with his “screw professional services, let me get into tech” path, which is similar to one I took.

But I finally had the good fortune of meeting him in person during a dinner with Tomas, Dan, Rafa, & Cailen in SF this summer - and man, what a character the guy was.

I knew after that dinner we had to have him on - he’s one of the most cerebral sellers I’ve ever met & the way he thinks about sales and life is so unique.

Raph Parker⁠ is the Chief Revenue Officer at ⁠Mandolin⁠, an AI company transforming healthcare operations.

Before Mandolin, Raph was the first go-to-market hire at Segment, helping scale the company from seed to its $3.2B acquisition by Twilio.

He then served as Chief Growth Officer at New Front Insurance, taking another company from seed to unicorn (with an IPO likely on the horizon).

He started his career as a corporate lawyer, then biked around the world for 2 years before stumbling into tech sales.

He joined us to talk about the psychology of early-stage selling, how to create social proof when nobody knows you, what to look for in a CEO, and why you should compete at the shallow end of the gene pool.

00:00 From Big Law to BDR: Raph's Unconventional Path into Sales

09:00 How to Evaluate CEOs: The Three Types of Founders

18:00 Prospect Theory: Why Early-Stage Selling is About Risk, Not Features

24:00 Creating Social Proof When You Only Have Two Customers

29:00 The Sales Call Hack: Flipping Informational Asymmetry

33:00 The "Bet My Career On It" Intro That Changes Everything

36:00 Why Nobody Believes Case Studies (And What Prospects Actually Want)

42:00 Hiring Early Sales Reps: The First Class to Greyhound Test

50:00 Distribution vs. Product: Why Great Ideas Fail

58:00 Compete at the Shallow End of the Gene Pool

Join a CEO who can evolve. The best early-stage CEOs aren't just wall-runners - they can transition to recruiting and retaining world-class exec talent as the company scales.

There are three types of founders - find the third bucket. Sociopaths can't build lasting teams, spectrum founders often struggle with the people transition. The third type? People who just never bought into the "get a safe job" programming - often kids of entrepreneurs or from cultures where starting companies is normal.

"Strong ideas, lightly held" is the trait to look for. Early-stage leaders need conviction to move fast, but flexibility to pivot when they're wrong. Stubbornness kills startups.

Know what you're optimizing for: cash, equity, or career development. These pull in different directions. Be honest with yourself about which one matters most right now - it changes what opportunities make sense.

People just want to get promoted. That's the real motivation behind every buyer. Your product isn't competing against the status quo - it's competing against their fear of looking bad to their boss.

Use informational asymmetry to hack social proof. When you only have two customers, say "our customers" (plural is a milestone). Drop names of companies you're talking to - not lying, just playing the game smarter.

Flip the script at the start of every call. Open with "if this isn't a fit, let's cut this early and I'll give you back your time." It earns you the right to ask real discovery questions and breaks the adversarial sales dynamic.

"I bet my career on this company" changes everything. When you explain why you personally joined, prospects see you differently - not as a quota-chasing rep, but as someone with skin in the game.

Nobody believes your case study. When a prospect asks for one, what they really want is to de-risk the decision. Connect them with a like-kind person instead - that's what actually removes the fear.

Compete at the shallow end of the gene pool. The smartest people all fight for the same prestigious roles. Meanwhile, less sexy industries (insurance, healthcare, PE-backed companies) have way less competition and often better economics.

Thanks for reading!

If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.

For those who are new, my name is Chris Balestras, partner @ VibeScaling - a GTM advisory, recruiting, media, and investing firm.

Where to find VibeScaling:

We work with most of the hottest AI-native startups in different capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LI.

🫡 cheers,

Chris