What does it take to scale a startup while prioritizing character, growth, and cutting edge technology?

In this episode, Sean Vassilaros, cofounder and CEO of KANNY, shares his entrepreneurial journey. He reflects on the challenges of raising funds, building a high character team, and how integrity, accountability, and respect play a pivotal role in hiring decisions.

Sean discusses the development of KANNY, from raising $800K in a friends and family round to building an MVP in just six weeks using AI powered development tools. He emphasizes the importance of short term goals in a startup and how focusing on three key metrics: product development, sales activity, and customer acquisition drives success. He also explores the concept of "return on character" and why it’s crucial for leaders to build teams based on high character values by holding teams accountable and ensuring they make decisions with integrity and respect.

Timestamps:

(00:00) Intro

(01:49) Sean Vassilaros’s background and journey

(03:12) The birth of KANNY

(05:45) Challenges and innovations in development

(06:20) Fundraising and building the MVP

(08:37) Accelerating development with AI

(17:13) Current status and future goals for KANNY

(22:16) Balancing work and philanthropy

Connect with our guest:

• Sean Vassilaros on LinkedIn: https://www.linkedin.com/in/seanv/
• Learn more about KANNY: https://www.kanny.com/

Connect with Daren:

• Daren Lauda on LinkedIn: https://www.linkedin.com/in/darenlauda/
• Learn more about Outset: https://outsetops.com/

This episode is sponsored by:

Learn more about ekai: https://yourekai.com/

What does it take to build and scale sales teams while balancing grit, empathy, and the rise of AI?

In this episode, Joe Moriarty, chief customer officer at Codio, shares his journey from QA tester to sales leader and founder. He reflects on the challenges of bootstrapping, doubling revenue under pressure, and the lessons learned from hiring his first sellers and working with outsourced BDRs.

Joe talks about the importance of curiosity, coachability, and attitude when building teams, and why empathy remains one of the most powerful differentiators in sales. He also opens up about the promise and pitfalls of AI in prospecting and content creation, and why human connection will continue to be essential for winning deals.

Timestamps:

(00:00) Intro

(01:34) Moving from QA into sales

(04:10) Overcoming challenges at Raven360

(06:35) Hiring and assessing sales team performance

(11:00) Why empathy matters in sales

(13:27) AI’s role in modern selling

(16:23) Wins with AI outbound resources

(17:56) Iterating and refining sales messaging

(19:05) Hiring and onboarding BDR teams

(21:51) Challenges of fractional CRO work

(24:16) Running rapid experiments in sales

(27:22) Using AI for GTM strategies

Connect with our guest:

• Joe Moriarty on LinkedIn: https://www.linkedin.com/in/joemoriarty/
• Learn more about Codio: https://www.codio.com/

Connect with Daren:

• Daren Lauda on LinkedIn: https://www.linkedin.com/in/darenlauda/
• Learn more about Outset: https://outsetops.com/

This episode is sponsored by:

Learn more about HLX: https://teamhlx.com

What does it take to tackle a seemingly impossible business challenge?

In this episode, Daren Lauda, host of How’d You Get That Number, shares a wild and unexpected story from his early career. Daren reflects on a moment when he was asked to turn a $695 XML editing tool into a multimillion-dollar project—something that seemed unthinkable at the time. But, as he reveals, leaning into the challenge transformed the company and set the stage for its eventual acquisition.

Timestamps:
(00:42) Intro
(01:17) The $695 to $50,000 transformation
(02:32) The impact of leaning in
(06:11) Shifting to operating margin expansion

Connect with Daren:

• Daren Lauda on LinkedIn: https://www.linkedin.com/in/darenlauda/
• Learn more about Outset: https://outsetops.com/