loader from loading.io

Turning a Side Hustle into a Full-Time Small Business, with Jonathan Kaylor

Measure Success Podcast

Release Date: 07/05/2022

Why Sales Data is Failing & How to Fix It show art Why Sales Data is Failing & How to Fix It

Measure Success Podcast

Most sales teams are working with bad data—and it’s costing them revenue. In this episode of the Measure Success Podcast, Robert Kall, CEO of Cien, explains how AI-powered sales intelligence is helping companies clean up their CRM data, improve forecasting, and drive more conversions. Key insights: ✅ How bad sales data hurts revenue growth ✅ Why most CRM data is inaccurate—and how to fix it ✅ How AI helps sales teams improve forecasting and performance If you want to eliminate bad sales data and unlock more revenue, don’t miss...

info_outline Successful Sales Strategies That Actually Work show art Successful Sales Strategies That Actually Work

Measure Success Podcast

Scaling a business takes focus, consistency, and the right people. Gui Costin, founder of Dakota, built a $40 billion sales and marketing firm by staying committed to long-term strategy and execution. In this episode, he shares how he grew his business, built an effective sales team, and created a system that works. Key insights: ✅ Why most sales teams fail and how to fix it ✅ The key to building a business that scales ✅ How private equity firms can raise more capital If you’re serious about growing your company the right way,...

info_outline How to Build a Business That Makes a Difference show art How to Build a Business That Makes a Difference

Measure Success Podcast

A sock company that changes lives? Yes. John and Mark X. Cronin, the team behind John’s Crazy Socks, prove that a business with heart can also be a business that thrives. In this episode, they share their journey from a small startup to a global brand, all while prioritizing inclusion, impact, and customer happiness. Key insights: ✅ How a simple idea became a multi-million dollar business ✅ Why purpose and giving back drive growth ✅ What businesses can learn from their customer-first approach If you want to build a company that stands for...

info_outline How to Grow Your Startup with Smart Branding show art How to Grow Your Startup with Smart Branding

Measure Success Podcast

Small businesses and startups need strong branding to stand out and grow. Jason Sherwood joins the Measure Success Podcast to explain why branding isn’t just about logos—it’s about creating trust, recognition, and customer loyalty. Key insights: ✅ Why branding matters for small businesses ✅ How to build a brand that attracts customers ✅ The biggest branding mistakes startups should avoid If you want to turn your business into a recognizable brand, this episode is packed with insights you can apply today. !  

info_outline The Truth About Starting a CPA Firm show art The Truth About Starting a CPA Firm

Measure Success Podcast

Going from a big firm to building your own CPA business takes courage, strategy, and the right mindset. Frank Milone, co-founder of FML CPAs, shares his journey from working at Ernst & Young to running a successful accounting firm. He explains the key lessons, mistakes to avoid, and how small firms can thrive today. Key insights: ✅ Why he left a major accounting firm to start his own ✅ The biggest challenges in running a CPA business ✅ How small firms can compete and grow If you’ve ever thought about starting your own business, this episode will...

info_outline How to Identify High-Drive Sales Talent show art How to Identify High-Drive Sales Talent

Measure Success Podcast

Hiring a great salesperson isn’t luck—it’s science. In this episode, Dr. Christopher Croner explains how companies can identify high-drive salespeople before they make a bad hire. He breaks down the psychology behind top-performing sales reps and how to build a team of closers. Key insights: ✅ The three essential traits of elite salespeople ✅ Why traditional hiring methods fail in sales ✅ How to predict whether a candidate will succeed If you want to stop guessing and start hiring salespeople who can close, don’t miss this...

info_outline The Four-Leaf Growth Model for Business Leaders show art The Four-Leaf Growth Model for Business Leaders

Measure Success Podcast

Growth without purpose leads to burnout and misalignment. In this episode of the Measure Success Podcast, Mark Mears explains why purpose-driven growth is the key to building successful businesses and engaged teams. He introduces the Four-Leaf Growth Model, a framework designed to help leaders create businesses that thrive and leave a lasting impact. Key insights: ✅ Why businesses need a clear purpose to grow sustainably ✅ The connection between leadership, culture, and profit ✅ How the Four-Leaf Growth Model drives long-term success If...

info_outline Why Great Branding Matters for Your Business show art Why Great Branding Matters for Your Business

Measure Success Podcast

Your brand is more than a logo—it’s the feeling people get when they interact with your business. In this episode, Jason Sherwood shares how businesses can build a bold, recognizable brand that attracts and retains customers. Key insights: ✅ Why branding is the foundation of business growth ✅ How to design a brand that stands out ✅ The biggest mistakes businesses make with branding If your business isn’t getting the recognition it deserves, this episode will help you refine your brand strategy for better results. Interested in being a...

info_outline How to Create a Culture of Trust and Accountability show art How to Create a Culture of Trust and Accountability

Measure Success Podcast

A business is only as strong as its team. Sean Glaze has worked with leaders across industries to improve teamwork, accountability, and communication. In this episode, he shares the mindset shifts and strategies needed to turn a group into a high-performing team. Key insights: ✅ Why most teams fail to work together effectively ✅ How to create a culture of trust and accountability ✅ The key to improving communication and team alignment If your team struggles with misalignment, lack of engagement, or poor collaboration, this episode will help you fix...

info_outline You Need to Know Key CFO Strategies show art You Need to Know Key CFO Strategies

Measure Success Podcast

Growth is exciting—but without strong financial strategy, it can lead to cash flow issues and missed opportunities. Jody Grunden, co-founder of Summit CPA, explains how Virtual CFOs help businesses scale without financial blind spots. Key insights: ✅ How forecasting helps businesses avoid financial pitfalls ✅ The most common cash flow mistakes—and how to fix them ✅ Why strategic CFO planning leads to long-term success If you want to scale with confidence and financial clarity, don’t miss this episode. Need CFO services? !   Connect...

info_outline
 
More Episodes

 

Jonathan Kaylor is a Midwest native, and his family have called the Pacific NW home since 2013. For nearly two decades, Jonathan led Customer Service and Inside Sales Teams for Banking, Manufacturing, and Distribution companies. Through Passages to Success, Jonathan is excited to be a student, storyteller, and advocate for Entrepreneurs and Small Business Owners. Outside of the BOB, Jonathan can be found enjoying coffee, beer, or wine, while sitting at the piano, strumming his guitar or cooking a great meal with friends and family.

Instagram: https://www.instagram.com/bizoverbeer/


In This Episode: 

Taking the dive from the corporate world into entrepreneurship is perhaps more popular than ever, especially after the COVID-19 pandemic. But to turn a side hustle into a viable business, entrepreneurs need community, knowledge about potential pitfalls, and confidence to take the plunge.

Our guest this week is one who made that jump: Jonathan Kaylor led customer service and inside sales teams for banking, manufacturing, and distribution companies for nearly two decades. Now, through his Passages to Success business networking community, he’s a student, storyteller, and advocate for entrepreneurs and small business owners.

Tune into the full episode for more about the most common challenges small business owners face, the advice Jonathan gives to those who have reached a plateau in their business growth, why building a superior company culture is so important to actually scaling a business, and more.  

 

Here’s a Glimpse of What You’ll Learn: 

 

  • How Jonathan’s “Business Over Beer” podcast was born, and how the COVID-19 pandemic changed his business model
  • Why Jonathan’s focus has been on micro-enterprise businesses and side hustlers, especially when they’ve reached a “plateau”
  • The two biggest challenges Jonathan sees small business owners struggling with 
  • Why business growth and business culture are inextricably linked 
  • The “invisible weight” that small business owners and CEOs carry around
  • How Jonathan measures success with his community of small business owners
  • What gave Jonathan the confidence to leave the corporate world and start his podcast and business 
  • The boundaries Jonathan has set outside of work, and how those help him measure success in his personal life

Resources Mentioned in This Episode: