n this episode of #StartupsUnedited, Jorge Soto sits down with Paul Yacoubian, Founder of Copy.ai (recently acquired by Fullcast) and angel investor, to break down how they rode the GPT-3 / OpenAI LLM wave early and turned a side project into a fast-growing AI startup.Paul shares exactly how Copy.ai:Spotted GPT-2/GPT-3 as the next big platform shiftLaunched Copy.ai as their fourth MVPGrew to $60K MRR in under 5 monthsUsed Twitter as their primary GTM + distribution channelBuilt a product-led growth (PLG) motion powered by self-serve and StripeKnew when it was finally time to quit VC and go full-time on the startupIf you’re a CEO or founder building in AI, PLG, or SaaS, this conversation is packed with tactical insights on:How to validate traction before leaving your jobWhy most side projects don’t fail on product, they fail on distribution & monetizationHow to dominate one growth channel instead of spreading thinWhat makes a strong founding team in the high-stress world of startupsWhy quality of life and ecosystem (Miami Tech vs Silicon Valley) now matter more than ever📌 Topics We Cover:00:00 – Intro & how Copy.ai got started01:30 – Why GPT-2 and GPT-3 were the wakeup call03:00 – Launching Copy.ai as a side project04:00 – Getting 2,000 signups in 48 hours from Twitter06:00 – Turning free users into paid MRR with PLG09:00 – How Paul thinks about traction, metrics & quitting your job13:00 – Founder mistakes, team dynamics & ego18:00 – Remote cofounding, trust, and staying sane21:00 – Why Miami Tech and lifestyle are now a real advantage🔗 Follow PaulTwitter: @PaulYacoubian🔥 If you’re building in AI, PLG, or B2B SaaS, subscribe for more unedited, tactical founder conversations.👇 Drop a comment:What’s the one channel you’re going to dominate for your startup this year — Twitter/X, LinkedIn, YouTube, something else?#CopyAI #PaulYacoubian #AIStartups #GPT3 #OpenAI #ProductLedGrowth #PLG #SaaS #StartupFounder #MiamiTech #StartupsUnedited

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In this episode of #StartupsUnedited, Jorge Soto sits down with Arjun Pillai — Cofounder & CEO at Docket, former CDO at ZoomInfo (Nasdaq: ZI), 2x startup exits, and investor — to break down the real journey of becoming a CEO, building in B2B SaaS, and knowing when it’s time to move on from a startup.

If you’re a founder, CEO, or early-stage operator, this conversation is packed with tactical insights you can actually use.

🔥 In this episode, we cover:

• From engineer to CEO: How Arjun went from configuring SAP reports in India to building and exiting his first company

• Make vs. Sell framework: Why in an early-stage startup everyone either makes the product or sells the product — and what that means for your first 10 hires

• Growing into the CEO role: Why the CEO title is “loaded,” and how it actually took 1.5–2 years for him to become a real CEO

• How to pick mentors and advisors:

  • Why big-name advisors on your cap table often don’t help

  • How to choose 2–3 operator mentors who are just 5–10 years ahead of you

  • When you outgrow a mentor and need to upgrade your bench

• When to quit your startup:

  • Time-boxing experiments (2–6 months)

  • Defining success in advance (customers, ARPU, revenue)

  • Avoiding the “zombie startup” that drifts with tiny traction and broken unit economics

• Finding product-market fit in B2B SaaS:

  • How Arjun thinks about the zero → seed stage

  • Running as many hypotheses and experiments as possible

• The future of conversational marketing:

  • Why real-time buying and selling is taking over

  • How chat and conversational marketing are transforming high-ACV, long-sales-cycle B2B

  • Why his team purposely focused on mid-market & enterprise instead of chasing everyone

💬 Who this is for:
B2B SaaS founders, CEOs, GTM leaders, and anyone navigating the brutal zero-to-seed journey, product-market fit, and the emotional rollercoaster of building companies.

⏱ Chapters (suggested):
0:00 – Intro & who is Arjun Pillai
2:00 – First startup, failures, and eventual exit
6:00 – Becoming a CEO vs. just having the title
10:00 – Make vs. Sell: the only two jobs in a startup
13:00 – How to pick (and outgrow) mentors and advisors
18:00 – When to quit: frameworks for calling it
24:00 – Product-market fit and early-stage experiments
30:00 – The rise of conversational marketing & B2B chat
38:00 – Building for mid-market & enterprise from day one

🔔 Subscribe for more raw conversations with founders, operators, and GTM leaders on Startups Unedited.

👉 Connect with Arjun on LinkedIn and check out his writing on building, scaling, and leading as a founder-CEO.

In this 2015 episode, Tomás De Matteis of #Sotoventures interviews Carlos Espinal, who is a partner at London, UK based startup accelerator and seed fund Seedcamp.

Mental health has been taboo for as long as I can remember especially in the United States. 10's of millions of Americans suffer from this common yet really mysterious condition. Some deal with it so bad that they are completely overwhelmed and can't function. Others find often unhealthy ways of coping such as substance abuse of other non-obvious addictions.   

In this 2016 episode with serial entrepreneur and Founder/CEO at The Alley in NYC, Jason Saltzman. Jason discusses dealing with anxiety as an entrepreneur within startups.

In 2016 Jorge interviewed Silicon Valley veteran Robert Scoble @Scobleizer at his home in the Bay Area of California. In this episode, he asks him what were the characteristics of a successful founder?

Jason Vargas is currently Co-Founder at RevShoppe. He's also one of the top SaaS sales influencers in Silicon Valley today. Back in 2016 Jason and Jorge sat down in an intimate setting to discuss what it's like to be an early sales person in Silicon Valley today.  Follow Jason on Linkedin at: https://www.linkedin.com/in/jasonvargas/

"Your job as a #founder is to teach people to care" Matt Hubert, CEO at Bitmatica​. Matt is a native Bay Area resident and self proclaimed nerd. He's one of Silicon Valley's best product minds and has been hacking since he was in diapers.   

Jorge sat down with Matt and to talk shop!  

Follow Matt on Linkedin: https://www.linkedin.com/in/aclimatt/

Kevin Spain is one of the top enterprise startup investors in Silicon Valley. His firm Emergence Capital is known for some of the early investments in Salesforce.com, Box, Veeva, Crunchbase, SalesLoft, Zoom.us, and more. Kevin sits down with Jorge in person at his Silicon Valley, HQ to discuss how view point on this whole startup game and what it's like to have been a founder now venture capitalist.  

Follow Kevin on Linkedin: https://www.linkedin.com/in/kevinspain/

In 2016, I sat down in Silicon Valley with Mikita Mikado, long before most people knew the name PandaDoc.

At the time, Mikita was already living the founder reality most people only talk about:• Immigrating to the U.S. from Belarus with a backpack and $400• Teaching himself entrepreneurship through execution, not theory• Turning a scrappy services business into a real software company• Learning firsthand why ideas don’t matter - execution does

This conversation is raw, honest, and surprisingly more relevant today than ever.

We talk about:

What entrepreneurship actually feels like (stress, responsibility, growth)

Why early startup teams need doers, not specialists

How to validate ideas without fear of them being “stolen”

Why every CEO is always selling - vision, talent, product, belief

Founder mental health, stress management, and high-performance habits

The real differences between Silicon Valley startup culture and the rest of the world

Why riding the right wave matters more than riding every wave

Mikita also shares a powerful analogy between surfing and startups - one of the best explanations of risk, timing, and conviction I’ve heard from a founder.

If you’re:👉 An early-stage founder👉 An immigrant building in tech👉 A solo builder or first-time CEO👉 Or someone questioning whether entrepreneurship is “worth it”This episode is for you.📌 This is a throwback - but the lessons are timeless.Subscribe for more unfiltered founder conversationsWatch more episodes of #StartupsUneditedDrop a comment if this resonated - especially if you’re building right now

In this #StartupsUnedited episode Jorge interviews his buddy Jack Smith about his journey in Silicon Valley, getting into Angelpad, launching Vungle, and more!