S2E4: Chris Buttenham (CEO, Reins)

Chris Buttenham shares his journey through near failure, the lessons learned from tough times, and how resilience and long-term vision drive entrepreneurial success.   Chris Buttenham is a tech entrepreneur and executive who is the co-founder and CEO of Reins, an alternative equity and financial data platform launched in 2024 to help independent small business owners (particularly in the skilled trades) implement modern incentive, retention, and succession plans.   More About Chris Buttenham   Reins (2024–Present): Buttenham co-founded Reins to bring corporate-style employee ownership tools to small businesses and contracting industries (such as HVAC, plumbing, and electrical services). Growing up working in his father's contracting business inspired him to build the platform, which offers specialized "ESOP Lite" frameworks and alternative phantom stock plans to reward long-term employees and navigate succession without giving up company control.   Obie & Lessonly Acquisition (2015–2021): He previously founded Obie (originally OneBase), an NLP-powered workplace Q&A and knowledge-management SaaS company. He was accepted into the 500 Startups accelerator program during this venture. Obie was acquired by Lessonly in 2021, which itself was subsequently acquired by Seismic. Following the acquisitions, he served as a Group Product Manager at Seismic until 2023.   —   Follow FFTC on Instagram @fromfoundertoceo   Connect with Tim Metzner on LinkedIn   Learn more about Chris Buttenham and his company at  https://www.myreins.com/  

Steven Plappert shares his intense experience navigating a last-minute fundraising crisis, the importance of investor relationships, and mental resilience strategies for founders.   Steven Plappert's recent experience serves as a powerful reminder of perseverance in the startup world.   More About Steven Plappert   Steven Plappert is an American entrepreneur, fintech executive, and endurance hiker best known as the co-founder and CEO of Forecastr, a software platform that helps early-stage and venture-backed startups manage their financial models and forecasting.   Forecastr: Co-founded the company in 2018 alongside Logan Burchett to move founders away from complex spreadsheets and into an intuitive financial planning and analysis tool.   Techstars: A two-time Techstars alumnus, participating in Techstars Anywhere in 2020. In August 2026, he was awarded the prestigious Techstars "GiveFirst Award" for his ongoing mentorship and transparency with other startup founders.   —   Follow FFTC on Instagram @fromfoundertoceo   Connect with Tim Metzner on LinkedIn   Learn more about Brent Beshore and his company at  https://forecastr.com/  

Brent Beshore shares how his entrepreneurial journey began with dropping out of law school, leading him down a path of relentless pursuit but also deep personal turmoil. Brent Beshore is an American entrepreneur, investor, and the founder and CEO of Permanent Equity (formerly adventur.es), a private equity firm based in Columbia, Missouri. More About Brent Beshore Permanent Equity: Founded in 2007, Brent Beshore's firm focuses on acquiring and holding cash-generating, small-to-medium-sized traditional businesses (such as in construction, manufacturing, and services) with the intention of keeping and stewarding them for decades rather than flipping them for a quick profit. Author: Brent Beshore wrote The Messy Marketplace: Selling Your Business in a World of Imperfect Buyers, a book focused on helping business owners navigate company transitions. — Follow FFTC on Instagram @fromfoundertoceo Connect with Tim Metzner on LinkedIn Learn more about Brent Beshore and his company at  https://www.permanentequity.com/brent-beshore

Carissa Reiniger discusses navigating debt, sacrifices, and the power of the small business community.   In a candid discussion with From Founder To CEO host Tim Metzner, Reiniger opens up about her harrowing experience and the lessons learned along the way.   Carissa Reiniger is a Canadian-born entrepreneur, author, and speaker best known as the Founder and CEO of Silver Lining, a company she started in 2005 with a mission to help small businesses become sustainable and profitable.   Carissa began her venture, Silver Lining, at just 22 years old, driven by a desire to support small business owners. Despite her success in creating a platform that has helped over 17,000 businesses, she faced a critical moment in 2008 when financial disaster loomed.   Originally from Edmonton, Alberta, she studied psychology at the University of Alberta before opting out of the academic path to build businesses. She is an active member of the global leadership community YPO and an instructor on Udemy. Her insights are frequently featured in outlets like The New York Times, Forbes, and Inc. Magazine.   LEARN MORE ABOUT CARISSA REINIGER'S IMPACT   The SLAP™ Methodology: With a background in psychology, Reiniger created the Silver Lining Action Plan (SLAP™). This tech-enabled, data-driven growth program uses behavior change science to help small business owners set and hit financial goals. Through this system, her company has worked with over 14,000 small businesses spanning more than 70 countries   Economic Justice Advocacy: Reiniger advocates heavily for financial inclusion, structure, and corporate support for local economies. Her initiatives with Impact5X have led to collaborations with major entities, including Google, Intuit, and The White House.   Follow FFTC on Instagram @fromfoundertoceo Catch up on past episodes at www.fromfoundertoceo.com Learn more about Carissa Reiniger and her company at www.silversmallbusiness.com

Todd Uterstaedt hands the reigns to Tim Metzner, new host of From Founder To CEO.   Tim Metzner, CEO of Fireroad, discusses getting involved in the start-up community during his co-op internship at the University of Cincinnati, finding Faith, and ultimately what led to him founding multiple startups.   Learn more about Fireroad and Fireroad Ventures at fireroad.io   FFTC Website: fromfoundertoceo.com

Alex experienced a spiritual awakening that led him and his co-founders to build the the most downloaded and used Catholic app in the world. As the business was transforming, so was Alex. Alex learned how important it is to "surrender" as you transition From Founder To CEO.

Joe is as real as it gets. He is a Founder and CEO who tells it like it is and pushes himself to get better and be better...every day. What I truly appreciate about Joe is his embrace of the idea that, "The obstacle is the way." As Founders, we know this, practice this, and embrace this...everyday. So, I was super excited to have Joe on the podcast to share his experiences as Founder of Spartan Races and his biggest obstacles shifting From Founder To CEO. Spartan came from Joe's mind as a former equities and derivatives trader on Wall Street. He turned his passion for extreme sports into a lifestyle for his family — and then into a business.

Enlisted Marine. Marine Officer. Husband. Father. Pharmaceutical Salesman. Firefighter. Founder & CEO. City Councilman. COVID-19 survivor. International Bestselling Author. These are just some of the roles that Zachary has excelled in during his short life. He certainly has had a big and growing impact on the firefighting profession, building safety, and now with his new book, "Warrior Entrepreneur," a big impact on thousands of Founders around the world. In this very candid interview, Zachary details why and how he relinquished day to day operations to a CEO, why his business is better for it, and advice to Founders, like you, who are considering such a decision.

When you meet Chideha for the first time, you immediately know. You know he is a special person. You know he cares about every person he comes into contact with. You know that he strives for excellence in everything his does. You know he actually is learning from YOU and incorporating YOUR life's lessons into HIS life. And, these are also the many reasons why I like his book. In this interview, Chideha talks about: ---> How his grandfather's assault from KKK members impacted him as a man and entrepreneur ---> The valuable lesson he learned about the power of referrals ---> What he did to recover from a painful "non-compete" lawsuit that nearly destroyed him and his business It's an incredible interview because Chideha is so transparent and willing to share HIS life's lessons.

Blinds.com is an incredible business story and Jay is an incredible Founder CEO. In his new book, he talks about the 4 Es...the foundational principles on which his success was built. After he and his team successfully built Blinds.com, he sold the company to Home Depot and continued leading for quite some time after. In this interview, Jay talks about: ---> What generosity looks like to him as a Founder & CEO. ---> A significant story about a time he felt short of his own expectations of a focus on humanity. It's an incredible interview because Jay is so candid and transparent about his own journey From Founder To CEO.