We help companies grow
Private investing to help entrepreneurs achieve their goals
What we believe
01. Life’s best lessons are hard to learn
Every person and company experiences adversity. We believe resiliency and persistence are keys to success in life and business. So those are the qualities we look for in people we partner with and companies we back. If you ever think someone else has a perfect life, get to know them better.
02. Growth drives value
It bears repeating that when companies grow, good things happen. Many of the businesses we work with are “sub-scale” when we first get involved, lacking all the resources they need to achieve their full potential. We bring capital, energy and fresh ideas to help our partner companies flourish.
03. Many private companies are overlooked
Lots of fantastic businesses get ignored by investors because of their size, location or industry. Most institutional investors are either looking for the next tech darling or for companies with substantial scale and profitability. And for whatever reason, they all seem focused on New York and Silicon Valley.
04. One person can’t do it all
We’ve run businesses, and we know what it’s like to feel pulled in a million different directions. Good entrepreneurs know they can’t do everything themselves, which is why they hire great people and why we roll up our sleeves with you to get things done.
05. Character hits our bottom line
In a culture where wealth is synonymous with success, the traditional values of honesty, generosity, and personal humility seem to be increasingly out of place. We expect every investment we make to be profitable, but we recognize that life and business are about more than mere dollars and cents.
We approach each investment with a long-term mindset.
Our investment focus
People
A company’s most important asset is its team. We want to back people with integrity, humility, a strong work ethic, and a passion for serving their customers and impacting their communities.
Industries
We’re looking across a broad range of sectors. In the past, we’ve worked with business services, technology, healthcare, and e-commerce companies, among others.
Deal Structure
We’ll do minority positions in early stage and growth companies or come alongside legacy-minded owners to acquire their family businesses and infuse new energy into an established profitable company.
Company Stage
We typically invest in companies that are above $5 million in annual revenue and profitable. For software-as-a-service companies, we require at least $1 million of recurring revenue.
Geography
Anywhere in the United States. Our most recent transactions were with companies headquartered in Arkansas, North Carolina, Texas, Idaho, Tennessee and Kentucky.
Upside Investments
Prior Investments
Our experience
Erik Stiller
Erik led our operational involvement in our investment in The Beaufort Bonnet Company. He helped build out the direct-to-consumer platform (website, digital marketing and strategy), which contributed to 70x growth during our involvement with the company.
Erik works closely with many of our companies, particularly in the areas of strategy, sales and marketing, and technology. He has a deep understanding of the digital marketing landscape and has helped numerous companies grow through thoughtful investment in the right channels, systems, and people.
Prior to Upside, Erik worked for The Boston Consulting Group and Google, and he spent five years as a professional baseball player in the Cleveland Indians and Houston Astros systems. He holds a BA from Princeton in Economics and Finance and an MBA from The Wharton School, where he focused on Entrepreneurial Management.
MANAGING PARTNERBIOFUN FACTS
Rick Apple
Rick is an experienced company operator and private equity investor who has focused on growth stage and lower middle market businesses across a variety of different industries.
Prior to Upside, he helped launch Altus, a leading provider of cloud-based business communication services to companies across the country. Rick served as COO of Altus for six years, building out the team, offering, and systems. In 2020 Altus was recognized on Inc. Magazine’s list of fastest growing private companies. Before that, Rick was the director of the Council & Enhanced Tennessee Fund, where he was the lead person responsible for sourcing, executing, and managing the private equity investments for the fund. Successful investments from that fund include ReDoc, Playmaker CRM, NContracts, Shareholder Insite, and FSi.
Rick began his career working in New York as a consultant with Oliver Wyman and as an investment banker with Wells Fargo Securities. His experience spans a wide variety of sectors including software and technology, business services, healthcare, banking and financial services, and ecommerce. Rick holds a Bachelor of Science in Engineering magna cum laude from Princeton University, a JD & MBA from Vanderbilt University, and is a member of the Tennessee Bar.
Kyle Mayo
A Nashville native and 2009 alumnus of the U.S. Naval Academy, Kyle served for over seven years as a Naval Special Warfare officer, deploying multiple times to southwest Asia and Asia-Pacific. He recently graduated from the Darden School of Business. Kyle has a passion for empowering managers and investors to recognize untapped potential of employees, customers, and communities.
Deal spotlight
The Beaufort Bonnet Company
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