About Us
Main Street Legacy Partners is an operator-led investment firm dedicated to acquiring and nurturing existing businesses with annual revenues of $2 million to $50 million. We focus on enhancing the sales, marketing, and operations functions of small to medium-sized businesses. Unlike other more conventional approaches where value creation is achieved through cost reduction, our strategy emphasizes growth, employee welfare, and fostering a positive culture. We prioritize sustainable expansion, the well-being of the team, and the cultivation of exceptional workplace environments.
Team
Ben Holloway
Co-Founder & Partner
Ben a Co-Founder and Partner of Main Street Legacy Partners. He brings over a decade of relevant experience in private equity, executive leadership, restructuring, and finance to the team.
Prior to Main Street, he was an investor and operator at Areté Capital Partners, a boutique restructuring advisory and investment firm, focused on providing independent fiduciary and stewardship services to companies experiencing significant growth pains, complex organizational change, or existential crisis. He served in multiple roles in a variety of businesses, from multi-unit franchises to public media companies.
Prior to Areté, he was a Vice President at Turn/River Capital, a technology-focused private equity firm. He managed and led several transactions with an aggregate value of $1B+. He held multiple board observer roles and worked very closely with the management teams.
Prior to joining Turn/River Capital, he started his career as a member of Intuit’s Rotational Development Program, where he spent time in Corporate Finance, Product Management, and Corporate Strategy & Development. During his time at Intuit, he led financial planning and budgeting processes, internal cost improvement initiatives, revenue optimization strategies, and M&A transactions.
Perhaps most importantly, he grew up in and around family businesses. The first was with Holloway Brothers Tools, an industrial distribution family business and later, Signature Furniture, a regional furniture installation business, where he spent many summers moving furniture in the sweltering Mid - Atlantic heat.
He earned his B.A. from Hamilton College and his M.B.A. from the University of Chicago Booth.
ben@mainstreetlegacypartners.com
TUYEE YEBOAH
Co-Founder & Operating Partner
Tuyee is a Co-Founder and Operating Partner at Main Street Legacy Partners with over a decade of experience in executive leadership, finance, business development and strategy in the US and Africa.
Prior to Main Street, Tuyee served as CEO for three companies within the Crown Peak Holdings portfolio across multiple industries including technology, gaming, and food and beverage.
Before here, he was a Vice President at Citizens Bank and J.P. Morgan where he led various corporate strategy efforts.
Prior to Citizens and JP Morgan, Tuyee was an associate at Antares Capital where he guided the structure and syndication for $30M to $1B+ senior secured cash-flow credit facilities supporting private equity buyouts.
Tuyee also runs an investment vehicle that provides funding to start-ups.
Tuyee holds a BA in Finance and Entrepreneurship from UW – Madison and an MBA from Harvard Business School.
tuyee@mainstreetlegacypartners.com
STEVE SHEIN
Co-Founder & Partner
Steve is a Co-Founder and Partner at Main Street Legacy Partners and brings over a decade of executive operating and venture capital experience.
Steve’s experience is represented most recently by his work with OCA Ventures, one of Chicago’s original pioneering Venture Capital firms, focusing on investing in Fintech and Enterprise Software.
Prior to OCA Ventures, Steve founded ReVal Trading, a fintech company that deployed capital in the derivative space and offered a data-analytics SaaS solution allowing subscribers to analyze financial markets without needing to build proprietary infrastructure or store large amounts of historical data. ReVal was acquired by a strategic buyer.
Prior to that, Steve spent several years as a macro trader.
Steve received his degree in Finance, Investment & Banking; Real Estate Economics from the Wisconsin School of Business. He completed his MBA at the University of Chicago Booth School of Business, and is a CFA Charterholder.
steve@mainstreetlegacypartners.com
NICK BROWN
Senior Associate
Nick is a Senior Associate at Main Street Legacy Partners, focusing on deal sourcing and execution. He brings experience in private equity, financial research, product management, and commercial due diligence to the team.
Prior to Main Street, Nick attended the MIT Sloan School of Management. While in business school, he worked part-time with various startups in B2B outsourced services and B2C entertainment products. He completed a summer internship with EY Parthenon's Software Strategy Group, which provides technical and commercial due diligence supporting software-focused private equity firms.
Prior to business school, he was an Associate at Ares Management, a leading global alternative investment manager. During his time at Ares, Nick spent time in both the firm's investment team and its quantitative research group.
Nick holds an MBA from MIT Sloan and a BA in Economics and English from Brown University.
nick@mainstreetlegacypartners.com
What Makes Us Different
We’re DIFFERENT FROM your traditional Private Equity Firm
Our experience spans the full spectrum of the deal-making process, from Venture Capital and Private Equity to Fortune 500 M&A activities. This experience equips us with a deep understanding of the inner workings of these groups. More importantly, it’s why we know these groups may not always represent the best option for small businesses. Below, we outline the distinctive approach of Main Street Legacy Partners compared to other alternatives available to small businesses:
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Private equity is fundamentally focused on profitability, frequently prioritizing cost optimization—or, more bluntly, cost-cutting—as a primary strategy. Upon acquiring a business, these firms set a clear endpoint, steering you and your team towards accelerated growth and reduced expenditures. In this model, your company might just be one among many in their portfolio, subject to a stringent 3-5 year plan aimed at enhancing the business for a subsequent sale.
While this approach can be effective under certain circumstances, it often does not align well with the needs and nuances of smaller companies. This misalignment is a primary reason why traditional private equity firms usually steer clear of operating in the small business sector.
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Strategic buyers, often your direct competitors, tend to operate at a slower pace due to the extensive internal reviews and approvals required before finalizing a deal. Entrusting your company's sensitive data to a rival can also pose significant challenges, adding a layer of complexity to negotiations.
Post-acquisition, the approach adopted by strategic buyers can mirror that of private equity firms, focusing on rapid integration and optimization. This transition may lead to significant changes within the team and could potentially dilute the unique identity that defines your company.
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You may have been contacted by a "Search Fund" which is essentially an individual who has backing to search for and acquire an individual business. These individuals are usually former employees of big companies and are looking to escape the corporate hierarchy and run their own business.
The issue is that they likely have little to no experience running a small business and have a limited amount of capital to draw from. Some may even be self-funding the deal and will be looking for loans and debt in order to finance the deal.
These buyers are unpredictable, have a challenging path to closing a deal, and more often than not, are tire kickers.
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Main Street Legacy Partners was established with a singular mission: to acquire and nurture outstanding small businesses. Our foundation is built upon leveraging the extensive experience we've gained in private equity, venture capital, and corporate mergers and acquisitions (M&A), aiming to offer a superior capital solution for small enterprises.
We are supported by committed capital from a cohort of seasoned investors and operator. Our strategy is long-term, affording us the opportunity to invest in people and cultivate business growth comprehensively. Our goal is to collaborate closely with you to develop a succession plan that aligns with your aspirations and ensures the continuity of your business's legacy.
If you’re contemplating the future of your business but are not yet ready to step away, we see this as an ideal opportunity. Let's explore partnership avenues to enhance your business, be it through acquisitions, team expansion, or other growth strategies. We are here to assist you in navigating these challenges, ensuring a seamless transition or expansion that respects the legacy of your business.
Investment Critera
We understand that businesses take many different forms, and as we draw on a broad base of successful operating and investing experience, our interest is not constrained to any single sector or type of business. However, we generally prefer to focus on businesses with certain attractive traits that are familiar to us and give us confidence in their long-term success
Industry
Our ideal target is in a business services or technology sector that is fragmented and offer substantial growth opportunities. We avoid industries that are highly cyclical, capital intensive and/or face significant external disruptive risks.
Size
We are primarily looking for a business with an enterprise value between $2M and $50M, and that generate over $1M of revenues and in excess of $500k in cash flow.
Company
Our focus is on an established and profitable business, and we avoid early-stage ventures or significant operational turnarounds. We are on the lookout for a business with greater than three years operating history, with stable growth and margins consistently more than 15%.
We are particularly interested in a business with the following characteristics: A high percentage of recurring revenues, a loyal customer base, strong market reputation and work culture, and a product or service offering with a distinct and sustainable competitive advantage.
If you are a broker or intermediary that can connect us with an interested seller of a business that meets our criteria, we would love to hear from you. We will pay industry standard finder’s fees in the event of a successful acquisition.
Our Process
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We start with an introductory phone call or two to discuss your business at a high level, backgrounds, and motivations. This enables us to determine whether it’s worth moving forward. We’re in-person business type of people, so we’re happy to make an effort to travel in order to get to know you and your business better.
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If after the confidential call, we determine that there might be a mutual fit, we execute an NDA for our mutual protection, and request a short list of documents. This typically includes financial statements over the past few years and some operating data/metrics.
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After completing our initial diligence, you can expect an Indication of Interest or IOI. This is a one-page letter that will provide the broad outline of a potential deal, which includes price range and other key conditions of the deal. This IOI is mutually non-binding, as there is still room for negotiation on terms. It serves as an indicator that we’re generally aligned on the big items such as price, deal structure etc.
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If the IOI is agreeable to both parties, it will be formalized into a Letter of Intent or LOI. This is a legally binding document that expands on all keys points mentioned in the IOI and also addresses other key considerations for the deal.
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This is the sprint to the finish. Once the LOI is signed, we’re drafting legal documents, doing a deep dive into the business, and having an accounting firm reviewing the books, all to better understand all aspects of your business.
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Once confirmatory diligence is complete and all the legal documents are signed we’re all set to close the transaction and begin working towards transitioning the business. Each transition plan is different and in many cases, the owners/sellers might be staying on to continue to work with us on operating the business. This is where the real work begins!
Current Portfolio
Franklin Alliance is a national network of CPA firms supporting each other to evolve, grow, and expand their market reach. Unlike Wall Street, which focuses on profits and shareholders, we care about Main Street – the core of local businesses. We believe in the transformative power of entrepreneurship, where individuals can create lasting change and impact their community. We also know how important it is to preserve traditions, expand legacies, and support growth at the community level. That’s why we empower CPA firms to reach their full potential and make a meaningful impact in their communities while maintaining their unique identity in local markets. With our platform, growing CPA firms can stay competitive and expand faster.
Select Transactions
Below are a few of the transactions we’ve worked on, both as and investors and as an operators.
Invicti provides dead-accurate, easy-to-use security scanners for enterprises to automatically find security flaws across thousands of websites, web applications, and web services. Its unique proof-based scanning technology yields industry-leading detection rates with false positive-free results every time.
Commio is the uniquely customizable, cloud-based communications API platform that makes it easy to deliver integrated voice and text messaging. Its APIs give customers total control, transparency, and redundancy for peace of mind built-in.
SkyZone is the largest owner, operator, and franchisor of indoor entertainment parks in the world with 300+ parks. With 500K+ members, cutting edge attractions, and strong social media presence, no company is better positioned in indoor active entertainment.
Kinova is a Canadian technology company that manufactures service robotics platforms and applications for personal assistance.
Huddle is an innovative document collaboration and client engagement portal that enables enterprises and governments to work seamlessly with external clients and partners.
Huddle was acquired by Ideagen, a publicly traded GRC Software business, in 2020.
Mailgun is the leading transactional email API platform built for developers.
Mailgun was acquired by Thoma Bravo, a leading private equity fund, in 2019. Turn/River retains a minority stake in the business. Mailgun was then acquired by Sinch, a public company in Europe.
Test IO is a test management system to implement explorative and test case-based testing in just a few minutes.
Test IO was acquired by EPAM, a global software engineering and consulting firm, in 2019.
Magnus Health provides a cloud-based student health record solution designed specifically for use in schools.
Magnus Health was acquired by Veracross, a school information systems provider, in 2019.
Contact Us
Ben Holloway
(302)-545-8995
ben@mainstreetlegacypartners.com
Tuyee Yeboah
(414)-737-1097
tuyee@mainstreetlegacypartners.com