From Addiction To Acquisition

Ryan Shank
Founder and CEO of Cameo Ventures, ShareWillow, and the exited founder of PhoneWagon
1hr 41min
July 27, 2023
About the Show

“I think it's honorable when you ask for help. People who are curious are the best type of people because they're trying to learn and they're trying to figure things out.”

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From building a successful startup to overcoming profound personal struggles, discover the inspiring journey of entrepreneur Ryan Shank. His story is a testament to resilience, willpower, creativity, and the pursuit of balance in life and business.

At a passing glance, Ryan Shank is a successful entrepreneur that turned a unique idea into a successful business acquisition. It may be tempting for the layman to understate Ryan’s success, but anyone who is familiar with the entrepreneur’s journey knows that success is the tip of a fearsome iceberg. In Ryan’s case, beneath the surface lies a tumultuous journey filled with struggles, addiction, recovery, and redemption. This is the side of entrepreneurship that isn't often discussed, but it's the one that truly defines the character and resilience of a remarkable person like Ryan Shank. Let's dive deep into his story and draw inspiration from his extraordinary journey.

Episode Resources: 

LinkedIn: ⁠https://www.linkedin.com/in/ryan-shank-94508328/⁠

Cameo Ventures: ⁠https://www.cameoventures.com/⁠

Sharewillow: ⁠https://www.sharewillow.com/⁠

Key Moments

From Addiction To Acquisition

The Unseen Battle Of An Early Entrepreneur

When we look at successful people, we often see the fruits of their labor without recognizing the sacrifices they've made. Ryan Shank is no exception. He's known for his entrepreneurial success, but few know about the personal battles he fought to get to where he is today.

Ryan Shank's journey towards creating PhoneWagon was one of tenacity and ingenuity. The idea was born out of a desire to transform the way businesses track and understand their phone call data. But turning this vision into a reality was no small feat. Ryan bootstrapped his way through the early stages, pouring his heart and soul into every aspect of the startup. Long hours were spent with “headsets on,” making countless sales calls to make PhoneWagon a success. His relentless dedication and hard work ultimately paid off, and PhoneWagon emerged as a testament to his entrepreneurial prowess and relentless determination. With its unique approach to call tracking and analytics, PhoneWagon became a game-changer in the industry, all thanks to Ryan's unwavering commitment to his vision.

Throughout this inspirational period of growth, Ryan's struggle with addiction was a hidden facet of his life that he skillfully concealed from the world. He found himself succumbing to the pressures of owning and operating his own business, relying on substances like adderall to get through the day. As time wore on, the signs that he was spiraling down the wrong path became increasingly evident. He began to realize that something needed to change, but the decision to actually make that change was one of the hardest he's ever had to make.

Choosing Recovery

The day that Ryan realized he had become the “weakest link” in his company. Recognizing that he was headed down a dangerous path, Ryan made the tough choice to step away from his company to seek treatment. It's a decision that takes an immeasurable amount of courage, and it's one that Ryan had the strength to make for his own well-being.

His journey to recovery was far from easy. It involved developing new habits and standards of living that were non-negotiable. He had to learn how to balance his personal life with his business, a feat easier said than done. But Ryan was determined to not let his struggles define him.

Asking for Help: A Lesson in Humility

One of the most significant changes that Ryan made was learning to ask for help. It's a simple yet profound step that many of us often overlook. In our efforts to appear strong and capable, we forget that it's okay to admit when we're struggling and to seek assistance.

For Ryan, this was a turning point in his journey. By reaching out for help, he was able to get the support he needed to navigate the challenging path to recovery. It wasn't a sign of weakness, but rather a testament to his strength and humility.

A Triumphant Return and a Successful Sale

After a grueling journey of self-discovery and recovery, Ryan returned to his business stronger than ever. His experiences had equipped him with a newfound perspective and a deeper understanding of his priorities. With renewed vigor and determination, he set out to take his business to new heights - all while maintaining his mental and physical health. He was so dedicated to this path that he even closed the sale of his business while living in a sober house with a group of peers in recovery. Their celebration was a steak dinner before curfew - Ryans’ treat, of course. 

Ryan managed to sell his business, marking a significant milestone in his entrepreneurial journey. His success story serves as a beacon of hope for anyone facing personal struggles while trying to build a business.

Ryan Shank's story is more than just a tale of business success. It's a testament to the human spirit's resilience and the power of change. His journey serves as a reminder that it's okay to struggle, it's okay to ask for help, and most importantly, it's okay to prioritize your well-being above all else.

As Ryan's story shows, success isn't just about professional achievements - it's about overcoming personal challenges and emerging stronger on the other side.


  • (00:00) Intro
  • (2:18) Early years 
  • (4:30) First experiences in hustling and sales
  • (14:03) My first sales job at a startup
  • (17:00) The entrepreneur’s mindset
  • (20:00) Going through my first acquisition
  • (25:07) Getting sued for a blogpost
  • (27:00) Over Communicate with your team
  • (30:50) Mastering inbound marketing
  • (30:45) What is product/market fit? 
  • (35:00) Getting acquired and exiting
  • (41:00) Becoming a founding entrepreneur
  • (44:45) Going from an idea to a real company
  • (54:30) Realizing I was struggling with an addiction
  • (57:31) We didn’t have “true product/market fit”
  • (1:04:00) What I learned from addiction treatment
  • (1:08:00) Getting acquired while in addiction treatment
  • (1:13:57) When employees steal from your company
  • (1:18:54) Why do acquisitions include escrow? 
  • (1:21:00) Life after selling my company
  • (1:24:31) Being transparent about my past
  • (1:26:50) Why entrepreneurs are often neurodivergent 
  • (1:31:30) Going all in on ShareWillow 
  • (1:39:26) My non-negotiables to maintain mental health


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