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/

What does it take to scale a community-led business without burning out or selling out?

In this episode, Mike Rizzo, founder of MarketingOps.com, shares how he transformed a personal need for connection into a thriving community of thousands of marketing operations professionals. Mike opens up about the scrappy early days, the pressure of funding a million-dollar conference, and the moment he realized they needed to shift from sponsorships to a sustainable membership model.

He talks about the tactical side of building community infrastructure, the lessons he learned from using Slack, and why he believes your go-to-market stack should be treated like a product.

Timestamps:

(00:00) Intro

(02:17) Mike’s start in marketing ops

(03:23) Founding MarketingOps.com

(05:06) Why Mike committed to a $1M event

(08:12) Cash flow stress and high-stakes decisions

(11:06) Defining community success

(14:38) Growth via automation and feedback loops

(17:24) The challenges of using Slack for community

(19:36) Building the chairperson program

(22:00) Going all in after layoffs

(25:02) Shifting to a membership model

(30:10) What makes MOps-Apalooza different

(32:11) Why GTM needs product thinking

(35:02) The vision for certified GTM professionals

Connect with our guest:

• Mike Rizzo on LinkedIn: https://www.linkedin.com/in/mikedrizzo/
• Learn more about MarketingOps.com: https://marketingops.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/

How do you navigate ambitious growth goals when the numbers don't add up?

In this episode, Rachel Trindade, CMO at FlavorCloud, shares her journey from marketing to revenue operations, shedding light on the challenges of scaling a B2B SaaS company and aligning teams to achieve big, bold goals. Rachel discusses the complexities of setting targets, the importance of balancing demand generation with brand-building, and the reality of working with tight resources while striving for high-growth objectives.

She also explores the critical role of collaborative planning across teams, how marketing and sales need to align for success, and the lessons learned from coming close to hitting a massive target despite the odds. 

Timestamps:

(00:00) Intro

(01:09) Rachel’s CMO journey

(03:04) Setting ambitious revenue targets

(07:36) Aligning sales & marketing

(10:15) Branding’s role in demand gen

(12:45) Overcoming resource constraints

(15:30) Bottoms-up planning & collaboration

(18:00) Adjusting after missed targets

(22:10) Lessons from FlavorCloud's growth

(25:30) Effective frequency in marketing

(28:45) Metrics that drive success

Connect with our guest:

• Rachel Trindade on LinkedIn: https://www.linkedin.com/in/racheltrindade/
• Learn more about FlavorCloud: https://flavorcloud.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/

How do you course-correct when 300% growth slips out of reach?

In this episode, Sean Crafts, partner at BLDG Labs and HLX, shares his journey from law school to building SaaS companies and chasing some of the most ambitious revenue goals in the industry. He walks us through the challenges of hitting a 300% growth target, why doubling sales headcount isn’t enough, and the power of aligning data across teams to create realistic and predictable plans.

Sean also breaks down the story behind a $19 million funding round, the hard lessons learned when forecasts fall short, and how his team turned a missed target into a stronger, more aligned company.

Timestamps:

(00:00) Intro

(01:34) Sean’s startup journey from AI to GTM

(06:08) The big, crazy number challenge

(18:47) Product release delays and sales impact

(19:06) Aligning teams with core metrics

(19:51) Building a collaborative ELT

(21:25) What Helix teaches companies today

(22:28) Data-driven consulting approach

(25:08) Challenges and successes in client engagements

(30:27) The importance of realistic goals

(36:45) What orgs get wrong about forecasting

Connect with our guest:

• Sean Crafts on LinkedIn: https://www.linkedin.com/in/seancrafts/
• Learn more about HLX: www.teamhlx.com
• Learn more about BLDG Labs: http://bldglabs.com/

Connect with Daren:

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

How’d You Get That Number?! is the show that asks B2B SaaS leaders one simple question: where did that goal actually come from?

Hosted by Daren Ladua and brought to you by Outset, each episode unpacks how career-defining KPIs, revenue targets, and growth goals were set in the first place and what happened next.

If you're building go-to-market teams or chasing big numbers, this is the real story behind the metrics.