Ryan is joined by the Co-Founder and COO of Obie insurance, Aaron Letzeiser, who shares how identifying one costly mistake led him to pivot and embrace AI for growth. Listen as Aaron talks about the critical decisions that make-or-break start-ups; from avoiding common founder missteps to leveraging partners for customer acquisition. Aaron also brings a tactical playbook for scaling with limited resources and shares actionable growth tactics.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS
Aaron pivoted from a free platform to a paid insurance offering based on 200+ customer discovery interviews
Partner with non-competing software platforms to embed services and decrease churn
Stay laser-focused on a single niche before expanding into adjacent markets
Use AI to drive core insurance underwriting and operations via visual recognition models
Market conditions like rising interest rates can significantly impact lending partners
Revisit sales processes and tighten SOPs during rapid scaling to ensure quality

BEST MOMENTS

"We really should have continued to listen to our customers and utilize that as the guiding principle of what we ended up building."

"Do one thing and do it well. That was advice we should have taken sooner."

"AI is endless. We use visual models to identify fire hydrants and drive insurance underwriting."

"As the team grows, how do we ensure the quality does not also drop off?"

Ryan Staley

Founder and CEO

Whale Boss

ryan@whalesellingsystem.com

www.ryanstaley.io

Ryan is joined by the Co-Founder and COO of Obie insurance, Aaron Letzeiser, who shares how identifying one costly mistake led him to pivot and embrace AI for growth. Listen as Aaron talks about the critical decisions that make-or-break start-ups; from avoiding common founder missteps to leveraging partners for customer acquisition. Aaron also brings a tactical playbook for scaling with limited resources and shares actionable growth tactics.
Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  
Explore becoming Superhuman here: <a href="https://superhumanrevenue.beehiiv.com/">https://superhumanrevenue.beehiiv.com/</a>
KEY TAKEAWAYS
<ul>
<li>Aaron pivoted from a free platform to a paid insurance offering based on 200+ customer discovery interviews</li>
<li>Partner with non-competing software platforms to embed services and decrease churn</li>
<li>Stay laser-focused on a single niche before expanding into adjacent markets</li>
<li>Use AI to drive core insurance underwriting and operations via visual recognition models</li>
<li>Market conditions like rising interest rates can significantly impact lending partners</li>
<li>Revisit sales processes and tighten SOPs during rapid scaling to ensure quality</li>
</ul>
BEST MOMENTS
"We really should have continued to listen to our customers and utilize that as the guiding principle of what we ended up building."
"Do one thing and do it well. That was advice we should have taken sooner."
"AI is endless. We use visual models to identify fire hydrants and drive insurance underwriting."
"As the team grows, how do we ensure the quality does not also drop off?"
Ryan Staley
Founder and CEO
Whale Boss
ryan@whalesellingsystem.com
<a href="https://www.ryanstaley.io/">www.ryanstaley.io</a>

How do you grow like a VC-backed SAAS company without taking on investors? What are the secrets that SAAS CEOs have that the rest of us don't? Do you want to create a lifestyle business, a performance business, or an empire?  How do you scale to an exit without losing your freedom?


Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best SAAS Founders, CEOs, and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.

This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Gina Bianchini (Founder of Mighty Networks and prior Co-Founder with Marc Andreessen) and Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin). This is where Scaling and Sales are made simple in 25 minutes or less.

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Sales, Business growth strategy, Founder, VP of Sales, CRO, Chief Revenue Officer, Technology, Leadership, CEO, Management, Hyper-Growth.

How do you grow like a VC-backed SAAS company without taking on investors? What are the secrets that SAAS CEOs have that the rest of us don't? Do you want to create a lifestyle business, a performance business, or an empire?  How do you scale to an exit without losing your freedom?
 Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best SAAS Founders, CEOs, and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Gina Bianchini (Founder of Mighty Networks and prior Co-Founder with Marc Andreessen) and Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin). This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Sales, Business growth strategy, Founder, VP of Sales, CRO, Chief Revenue Officer, Technology, Leadership, CEO, Management, Hyper-Growth.

The Scale Up Show

How do you grow like a VC backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire?  How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO’s and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak),  Andrew Gazdecki (Founder of Microacquire), Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin) and many more
This is where Scaling and Sales are made simple in 25 minutes or less.

How do you grow like a VC backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? &nbsp;How do you scale to an exit without losing your freedom? Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO&rsquo;s and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset. This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World&rsquo;s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak),&nbsp; Andrew Gazdecki (Founder of Microacquire), Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin) and many more This is where Scaling and Sales are made simple in 25 minutes or less.

How to Pivot and Embrace AI for Growth with Aaron Letzeiser Co-Founder & COO of Obie

This is part two of Ryan’s conversation with Aytekin Tank, the founder and CEO of Jotform, a form building platform created from his desire to help automate the communication between people. Author of Automate Your Busy Work, Aytekin shares his framework for cutting time spent on menial tasks by 70% and reveals how AI is transforming Jotform's products. From the importance of prioritization to embracing system thinking, this episode shares actionable insights for entrepreneurs looking to scale their businesses efficiently in the age of AI.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  



Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS
Clarify priorities through time audits to understand how you spend your time and identify tasks to automate or delegate.
Embrace "laziness" and impatience as drivers for finding efficient solutions and automating repetitive tasks.
Make time to save time by researching automation tools and learning new technologies like AI and prompt engineering.
Adopt a system thinking approach, transitioning from an individual contributor to a manager of automations and AI.
Use tools like Dead Man's Snitch to monitor and maintain your automated systems, ensuring they continue to function properly.
Focus on important tasks that are often not urgent, following Eisenhower's wisdom on prioritization.
Leverage AI for code reviews and fraud detection to significantly improve efficiency and accuracy in tech development.
Explore AI integration in products through copilots and agents to reduce learning curves and enhance user experience.

BEST MOMENTS

"Bill Gates said, 'I would always hire a lazy person to do a hard job. Because he will find an easy way to do it.'”

"Eisenhower says that he had two kinds of problems, the urgent and the important. The important are never urgent and the urgent are seldom important."

"With copilots, you can actually give people an option... They don't have to learn it anymore, they can just tell us what they need."

"It's about figuring out your priorities. For example, for me, in the morning, that's my best time."

"We use AI for code reviews... It becomes easier because it's going to catch many types of code problems."

Ryan Staley

Founder and CEO

Whale Boss

ryan@whalesellingsystem.com

www.ryanstaley.io

This is part two of Ryan’s conversation with Aytekin Tank, the founder and CEO of Jotform, a form building platform created from his desire to help automate the communication between people. Author of <a href="https://www.amazon.co.uk/Automate-Your-Busywork-Achieve-Brain/dp/1119901731">Automate Your Busy Work</a>, Aytekin shares his framework for cutting time spent on menial tasks by 70% and reveals how AI is transforming Jotform's products. From the importance of prioritization to embracing system thinking, this episode shares actionable insights for entrepreneurs looking to scale their businesses efficiently in the age of AI.
Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.   
Explore becoming Superhuman here: <a href="https://superhumanrevenue.beehiiv.com/">https://superhumanrevenue.beehiiv.com/</a>
KEY TAKEAWAYS
<ul>
<li>Clarify priorities through time audits to understand how you spend your time and identify tasks to automate or delegate.</li>
<li>Embrace "laziness" and impatience as drivers for finding efficient solutions and automating repetitive tasks.</li>
<li>Make time to save time by researching automation tools and learning new technologies like AI and prompt engineering.</li>
<li>Adopt a system thinking approach, transitioning from an individual contributor to a manager of automations and AI.</li>
<li>Use tools like Dead Man's Snitch to monitor and maintain your automated systems, ensuring they continue to function properly.</li>
<li>Focus on important tasks that are often not urgent, following Eisenhower's wisdom on prioritization.</li>
<li>Leverage AI for code reviews and fraud detection to significantly improve efficiency and accuracy in tech development.</li>
<li>Explore AI integration in products through copilots and agents to reduce learning curves and enhance user experience.</li>
</ul>
BEST MOMENTS
"Bill Gates said, 'I would always hire a lazy person to do a hard job. Because he will find an easy way to do it.'”
"Eisenhower says that he had two kinds of problems, the urgent and the important. The important are never urgent and the urgent are seldom important."
"With copilots, you can actually give people an option... They don't have to learn it anymore, they can just tell us what they need."
"It's about figuring out your priorities. For example, for me, in the morning, that's my best time."
"We use AI for code reviews... It becomes easier because it's going to catch many types of code problems."
Ryan Staley
Founder and CEO
Whale Boss
ryan@whalesellingsystem.com
<a href="https://www.ryanstaley.io/">www.ryanstaley.io</a>

From Busy Work to AI Mastery: Aytekin Tank's Secrets to Efficient Growth Part 2

Aytekin Tank is the founder and CEO of Jotform, a form building platform created from his desire to help automate communication between people. Aytekin, a trained developer, bootstrapped Jotform from scratch. He is also the author of "Automate Your Busy Work" and is passionate about writing and sharing business advice.

He joins Ryan to discuss his experience of bootstrapping his company from the ground up and the strategies that helped accelerate the growth of the business.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  



Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS
Growth often takes time in the first few years of a bootstrapped company but Aytekin highlight the many positives of bootstrapping your company, including the independence you retain and less pressure externally.
Jotform is a free product but where there are paid add ons and options.
Aytekin wanted to create a simple to use form building platform after being unable to find what he needed himself.
The pandemic helped accelerate the transformation into digital and Jotform was on of the businesses to feel that.
A developer by trade, Aytekin had to train himself on everything including the management of people.
Creating a culture of independence and innovation, supported with a clear mission statement has helped Aytekin grow his teams and scale the company effectively.
To compete with the growing competition, including Google forms, Aytekin focuses on automation and delegation in his own work and across his teams.

BEST MOMENTS

“It’s about the [business] journey, it’s not about reaching one state, it’s about what we can do for people”

“I love seeing other people use it [Jotform] and get value from it”

“It’s a very horizontal product, everybody uses forms”

“Starting my company was all about independence, building my own product”

"We also improved out product in terms of automation"

Ryan Staley

Founder and CEO

Whale Boss

ryan@whalesellingsystem.com

www.ryanstaley.io

Aytekin Tank is the founder and CEO of Jotform, a form building platform created from his desire to help automate communication between people. Aytekin, a trained developer, bootstrapped Jotform from scratch. He is also the author of "Automate Your Busy Work" and is passionate about writing and sharing business advice.
He joins Ryan to discuss his experience of bootstrapping his company from the ground up and the strategies that helped accelerate the growth of the business.
Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.   
Explore becoming Superhuman here: <a href="https://superhumanrevenue.beehiiv.com/">https://superhumanrevenue.beehiiv.com/</a>
KEY TAKEAWAYS
<ul>
<li>Growth often takes time in the first few years of a bootstrapped company but Aytekin highlight the many positives of bootstrapping your company, including the independence you retain and less pressure externally.</li>
<li>Jotform is a free product but where there are paid add ons and options.</li>
<li>Aytekin wanted to create a simple to use form building platform after being unable to find what he needed himself.</li>
<li>The pandemic helped accelerate the transformation into digital and Jotform was on of the businesses to feel that.</li>
<li>A developer by trade, Aytekin had to train himself on everything including the management of people.</li>
<li>Creating a culture of independence and innovation, supported with a clear mission statement has helped Aytekin grow his teams and scale the company effectively.</li>
<li>To compete with the growing competition, including Google forms, Aytekin focuses on automation and delegation in his own work and across his teams.</li>
</ul>
BEST MOMENTS
“It’s about the [business] journey, it’s not about reaching one state, it’s about what we can do for people”
“I love seeing other people use it [Jotform] and get value from it”
“It’s a very horizontal product, everybody uses forms”
“Starting my company was all about independence, building my own product”
"We also improved out product in terms of automation"
Ryan Staley
Founder and CEO
Whale Boss
ryan@whalesellingsystem.com
<a href="https://www.ryanstaley.io/">www.ryanstaley.io</a>

Automating Communication: Scaling a Bootstrapped Business with Jotform Founder Aytekin Tank

Ryan Staley interviews Randy Wootton who shares his incredible journey from the U.S. Navy to working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing. Randy reveals the seven secrets of success for SaaS CEOs, offering invaluable insights on navigating the challenges of scaling a business.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  



Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS
Randy Wooten transitioned from a successful career in the U.S. Navy and working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing.
As a CEO, Randy emphasizes the importance of delivering shareholder value, establishing a winning strategy, shaping company values and standards, building an effective executive team, managing the board and investors, allocating capital strategically, and investing in your personal growth.
Randy discusses the challenges of selling to CFOs compared to CMOs, highlighting the need for a different go-to-market motion that involves bringing in influencers and references, as CFOs tend to be more introverted and rely heavily on relationships when making purchase decisions.
Maxio uses the McKinsey Horizon Model to allocate funds for current and future growth, dedicating resources to core business (Horizon 1), near-term opportunities like payments (Horizon 2), and long-term game-changing initiatives (Horizon 3).
Randy believes that AI will significantly impact go-to-market strategies, with boards expecting companies to incorporate AI efficiency assumptions into their fiscal year 2025 planning, and he advises businesses to start experimenting with AI tools now to stay ahead of the curve.
To navigate the challenges of being a CEO, Randy recommends finding a mentor who has been in a similar position, working with a coach to improve interpersonal effectiveness, joining peer groups like EO or YPO, and cultivating a personal advisory board for support and guidance.
Randy highlights the importance of being a system of record and having differentiated data that can be leveraged with AI to create intelligent engines that offer benchmarks and insights to help customers run their businesses more effectively.
By sharing his experience co-founding the VetForce platform at Salesforce, which empowers military veterans, Randy demonstrates his commitment to making a positive social impact alongside his professional achievements.

BEST MOMENTS

"I am there to deliver shareholder value. That's primarily driven by delivering the results." 

"One of the things when I became CEO, the first time was I wanted a mentor, someone who had been in the same context." 

"I think for my own career growth, I had reached this inflection point where I thought, gosh, the patterns that I've seen in this scenarios, would it apply to a different vertical in this case, selling to the CFO?"

"Unless you're absolutely crushing it and everyone's gonna make a whole bunch of money, like there is [something] everyone starts to revert to it's like Maslow’s hierarchy of need. They're all nice until it becomes, okay, how are we going to carve up the pie?" 

"I think anyone who's truly appreciative of what's happened in their life will also recognize how much luck has played and connections, and we'll be willing to give back to other folks." 

Ryan Staley

Founder and CEO

Whale Boss

ryan@whalesellingsystem.com

www.ryanstaley.io

Ryan Staley interviews Randy Wootton who shares his incredible journey from the U.S. Navy to working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing. Randy reveals the seven secrets of success for SaaS CEOs, offering invaluable insights on navigating the challenges of scaling a business.
Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.   
Explore becoming Superhuman here: <a href="https://superhumanrevenue.beehiiv.com/">https://superhumanrevenue.beehiiv.com/</a>
KEY TAKEAWAYS
<ul>
<li>Randy Wooten transitioned from a successful career in the U.S. Navy and working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing.</li>
<li>As a CEO, Randy emphasizes the importance of delivering shareholder value, establishing a winning strategy, shaping company values and standards, building an effective executive team, managing the board and investors, allocating capital strategically, and investing in your personal growth.</li>
<li>Randy discusses the challenges of selling to CFOs compared to CMOs, highlighting the need for a different go-to-market motion that involves bringing in influencers and references, as CFOs tend to be more introverted and rely heavily on relationships when making purchase decisions.</li>
<li>Maxio uses the McKinsey Horizon Model to allocate funds for current and future growth, dedicating resources to core business (Horizon 1), near-term opportunities like payments (Horizon 2), and long-term game-changing initiatives (Horizon 3).</li>
<li>Randy believes that AI will significantly impact go-to-market strategies, with boards expecting companies to incorporate AI efficiency assumptions into their fiscal year 2025 planning, and he advises businesses to start experimenting with AI tools now to stay ahead of the curve.</li>
<li>To navigate the challenges of being a CEO, Randy recommends finding a mentor who has been in a similar position, working with a coach to improve interpersonal effectiveness, joining peer groups like EO or YPO, and cultivating a personal advisory board for support and guidance.</li>
<li>Randy highlights the importance of being a system of record and having differentiated data that can be leveraged with AI to create intelligent engines that offer benchmarks and insights to help customers run their businesses more effectively.</li>
<li>By sharing his experience co-founding the VetForce platform at Salesforce, which empowers military veterans, Randy demonstrates his commitment to making a positive social impact alongside his professional achievements.</li>
</ul>
BEST MOMENTS
"I am there to deliver shareholder value. That's primarily driven by delivering the results." 
"One of the things when I became CEO, the first time was I wanted a mentor, someone who had been in the same context." 
"I think for my own career growth, I had reached this inflection point where I thought, gosh, the patterns that I've seen in this scenarios, would it apply to a different vertical in this case, selling to the CFO?"
"Unless you're absolutely crushing it and everyone's gonna make a whole bunch of money, like there is [something] everyone starts to revert to it's like Maslow’s hierarchy of need. They're all nice until it becomes, okay, how are we going to carve up the pie?" 
"I think anyone who's truly appreciative of what's happened in their life will also recognize how much luck has played and connections, and we'll be willing to give back to other folks." 
Ryan Staley
Founder and CEO
Whale Boss
ryan@whalesellingsystem.com
<a href="https://www.ryanstaley.io/">www.ryanstaley.io</a>

How to Pivot and Embrace AI for Growth with Aaron Letzeiser Co-Founder & COO of Obie

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