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Buying a business is a great way to become an entrepreneur or expand your company’s portfolio. Selling a business, on the other hand, is considered a big step in an entrepreneur’s journey and is often an emotional decision as much as a financial one. Whether you are on the seller or buyer side, there’s a lot to consider and learn.

Learning from experts who have done it all and seen it all is a great start. In this article, we share the top pieces of advice, secrets, success stories, and lessons learned from the various experts we spoke with in the buying, selling, and investing space.

Lisa Feria, Stray Dog Capital

According to Lisa, founders should lead with conviction, confidence, and self-awareness in areas they don’t perform as well. Self-perception is key in determining which aspects of your business you should handle yourself and which ones are better off in someone else’s hands. Leveraging other people’s skills and expertise is often more beneficial for the business.

Stray Dog Capital is a venture capital fund investing in innovative, early-stage companies across the food, beverage, and biotechnology sectors that are driving a healthier, humane, and more sustainable future. Stray Dog Capital supports its portfolio of investments with broad experience from its team of entrepreneurs, operators, advisors, and investors.

Learn more:Lisa Feria, Stray Dog Capital

Andrew Romans, 7BC Venture Capital

When structuring an investment portfolio, Andrew emphasizes the importance of diversification. Instead of expending all your resources on one company, stockholders should allocate their finances to maximize ROI. To streamline the process, create a spreadsheet that outlines a framework for your portfolio. Due diligence is vital; make sure you take the time to learn before acquiring a new business.

7BC Venture Capital is a venture capital fund focused on investing in and supporting artificial intelligence (AI), financial technology (FinTech), software infrastructure, and enterprise and consumer internet companies. The company’s mission is to leverage the power of capital, technology, and its US and international corporate network to solve the most pressing problems connecting and underpinning the digital economy.

Learn more:Andrew Romans, 7BC Venture Capital

Lori Ferrara, Treehouse Global Ventures

When initiating a business deal, it’s important to remember that it’s a lengthy and often arduous process. Buyers can be demanding and deceiving, so sellers should exercise meticulous judgment before accepting an offer. Lori advises drafting a contract agreement to mitigate bluffs and ensure equal and fair distribution. She reminds business owners that it’s perfectly acceptable to withdraw from a deal that doesn’t serve you.

Treehouse Global Ventures (“TGV”) is a private equity fund that was formed by three leading national women investors/influencers. The firm specializes in providing growth capital for touching/non-plant touching cannabis companies. TGV’s management team is composed of investors who have a combined 30 years of experience in the cannabis space and know how to enhance value for investors and business owners.

Learn more:Lori Ferrara, Treehouse Global Ventures

Will Chuchawat, Proskauer

Will has been involved in hundreds of deals, learned valuable lessons, and faced many challenges. As an expert in the business investment space, he asserts the importance of partnering with straightforward people who can maintain transparency about the nature of the company you’re looking to acquire. He also recommends conducting your own research into the business to assess its functionality.

Proskauer is a full-service law firm with a team of 800+ lawyers serving clients from offices located in the leading financial and business centers in the Americas, Europe, and Asia. The firm works with asset managers, major sports leagues, Fortune 500 companies, entertainment industry legends, and other industry-redefining companies. Proskauer is entrepreneurial, inclusive, and committed to making a difference for good.

Learn more:Will Chuchawat, Proskauer

Paul Irving, GTMfund

Sometimes, founders avoid buying a company from owners who have never founded their own enterprise, as they believe it affects the quality of the business. Yet, Paul says this shouldn’t be a deciding factor, and founders should assess the owner’s business history to determine their ability to build and scale their company. It’s critical to network with people who have a wealth of different career experiences as it provides alternative problem-solving methods.

GTMfund is an early-stage fund focused on B2B SaaS startups. The company helps exceptional founders with great products scale their go-to-market and generate revenue. Its 140+ investors are GTM Leaders who have seen zero to IPO at companies like Salesforce, Okta, Tableau, Mulesoft, Zoom, Snowflake, Segment, ServiceNow, DocuSign, and many more.

Learn more:Paul Irving, GTMfund

Raghavakumar Komanduri, Simon School Venture Fund

In venture capitalism, there are three factors that directly impact the success of any startup or early-stage business. According to Raghavakumar, founders and business owners must analyze the current market, develop strategies to outperform the competition, and understand the firm’s owners to determine if they are a good fit for your company. It takes experience and mentoring from the right people to learn how these elements function individually and how they influence each other.

The Simon School Venture Fund (SSVF) is an early stage seed fund run by MBA and Master’s students at the Simon School, University of Rochester. The purpose of the Simon School Venture Capital Fund is to create unique and experiential learning opportunities for students with respect to entrepreneurship and venture capital investment. The Fund is guided by an alumni advisory board that consists of VCs, successful entrepreneurs, and accomplished professionals in finance, law and other disciplines.

Learn more:Raghavakumar Komanduri, Simon School Venture Fund

Judy Sindecuse, Capital Innovators

When selling a business, it’s important to develop criteria that attracts investors. According to Judy, investors seek companies with practical business models that generate ROI. Methodical and consistent company practices and strategies demonstrate direct success and guarantee profitability for your investors.

Capital Innovators is the innovation engine for startups, corporations, and universities. Through its nationally recognized seed program, Capital Innovators has been ranked as a top accelerator four years consecutively and featured in Entrepreneur, Forbes, CB Insights, Inc., and TechCrunch, among others. In addition to the core accelerator program, Capital Innovators is creating a new model for innovation, bringing corporations, universities, and startups together like never before.

Learn more:Judy Sindecuse, Capital Innovators

Charlie Banks, VentureSouth

Charlie number one advice for assimilating into a new company is to avoid the ‘founder syndrome’ – meaning accept change and don’t try to overpower the organization. It would greatly benefit you and your business if you network with and learn from other founders or those who have more experience than you so you receive best practices and avoid making the same mistakes they did.

VentureSouth is an early-stage venture firm that develops and manages angel investment groups and funds throughout the Southeast. Since its inception with the Upstate Carolina Angel Network in 2008, VentureSouth has grown to include more than 450 investors across a dozen angel groups and funds. This makes them one of the largest angel investment organizations in the United States, having deployed over $80 million in nearly 100 companies.

Learn more:Charlie Banks, VentureSouth

Skip Vaccarello, 1Flourish Capital

Skip says that the key is in humility – you do the best you can while acknowledging you don’t know everything. Be self-aware and humble enough to recognize your weaknesses while maximizing your strengths. Learn from others and delegate tasks to those who can do them better than you can.

1Flourish Capital is a venture firm that invests in and mentors early-stage tech startups. They are faith-driven and seek out entrepreneurs with strong character and even stronger cultures. They are comprised of Silicon Valley CEOs and Venture Capitalists with proven track records in their industries. Some of their companies include WeThink, Kukun, Equifi, and Melzi to name a few.

Learn more:Skip Vaccarello, 1Flourish Capital

Evan Singer, First Guaranty Bank

According to Evan, having a strong culture is a crucial part of making your business appealing to buyers. You need a distinct culture that a buyer can carry through the transition to ensure your company’s long-term success. A poor company culture can destabilize the entire buying and selling process.

First Guaranty Bank has proudly served the people of Louisiana for over 87 years. They are well-positioned to meet their customers’ needs and expectations with their ability to make loan decisions on a local level. While other banks come and go, First Guaranty Bank is backed by three generations of banking trust.

Learn more: Evan Singer, First Guaranty Bank

Paul O’Brien, Mediatech Ventures

Paul advises against investing in startups unless you have the necessary funds or experience. According to Paul, 15-18 of every 20 investments will result in a loss. You’re more likely to achieve success by acquiring an established company in an industy that’s familiar to you. Paul maintains that investing in startups is for people who have a lot of money to lose and are willing to give it away despite the risk.

MediaTech Ventures is the leading global venture development firm for the media and technology industries, employing a proprietary framework of global partnerships to connect capital and people-advancing opportunities in modern media. MediaTech works at the heart of the industry, assisting artists, developers, producers, entrepreneurs, and financiers. MediaTech works to create jobs, fund opportunities, and celebrate media innovation.

Learn more: Paul O’Brien, Mediatech Ventures

Ziad Makkawi, EQUIAM

Ziad’s number one tip for investors is to trust your gut and work hard. He strives to learn on a consistent basis, and the people he learns the most from are frequently those he works alongside. Ziad believes that if you gather quality data, work hard, and employ your knowledge, you will be well on your way to success.

EQUIAM is a non-traditional, systematic venture capital firm. To make investment decisions, they employ highly researched, proprietary, data-driven algorithms. EQUIAM is committed to finding great firms and capturing the high returns associated with these bets and bringing world-class portfolio engineering practices to the private markets, mitigating risk and increasing long-term performance. This focus, combined with their proven execution capability, enables EQUIAM to provide investors with diversified portfolios of private firms designed to outperform in even the most difficult environments.

Learn more: Ziad Makkawi, EQUIAM

Maureen Boyce, Good Growth Capital

Maureen offers a few key tips for selecting investments that will set you up for success. First, be patient as you weigh your options for locating a suitable company. Second, be persistent. While looking for the right investment, evaluate potential ventures quickly. Finally, be picky. Look for a coachable team with an industry-leader. If you stick to Maureen’s advice, you can make wise investments.

Good Growth Capital is a majority-women and minority-owned early-stage venture capital firm that invests in transformative start-ups in industries such as health technology, green technology, and data sciences. Good Growth Capital, with offices in both Charleston, SC and Boston, MA, has a diverse scouting pool in the Southeast as well as early-stage technology accelerators at MIT and throughout the Research Triangle. Good Growth Capital and its funds meet both ESG and UNSDG impact goals

Learn more: Maureen Boyce, Good Growth Capital

Chris Blake, Beacon Mobility

Beacon Mobility
According to Chris, being disciplined and maintaining strong relationships are critical in making your business more appealing to potential buyers. Strong relationships based on mutual respect and understanding are essential when purchasing and integrating new businesses. On the other hand, staying disciplined will allow you to walk away from a deal if there are red flags. Chris suggests that it is never too late to back out of a deal if the fit isn’t right.

Beacon Mobility is a growing family of companies dedicated to meeting their customers’ diverse needs. Beacon Mobility takes pride in their ability to create customized, mobility-based solutions that empower people to get where they’re going. They advocate for safe, compassionate, and inclusive environments that provide their communities with quality transportation solutions.

Learn more: Chris Blake, Beacon Mobility

Alan Marrullier, ClearCap Strategic Advisors, LLC

ClearCap Strategic Advisors, LLC
Alan says one of the most difficult aspects of selling a business is being honest with oneself. Selling a business is not the same as selling a home. Many sellers have no idea what they truly want and don’t understand the distinctions between different types of transactions or buyers. Alan believes that most sellers do not conduct an objective self-evaluation to determine their realistic buyers.

ClearCap Strategic Advisors is an investment bank with unique financial advisory skills that are focused on meeting the needs of business entrepreneurs and middle market company shareholders. Led by senior bankers, they specialize in assisting mid-sized companies in achieving strategic liquidity objectives while maximizing shareholder value. ClearCap also helps to establish long-term goals and execute them through plans made to satisfy both ownership and corporate interests.

Learn more: Alan Marrullier, ClearCap Strategic Advisors

Daniel Acheampong, Visible Hands VC

Daniel describes the entrepreneurial journey as a difficult but rewarding experience. Daniel advises aspiring entrepreneurs to not be discouraged when challenges arise but to keep taking steps towards what they believe is worthwhile. While it may not be easy, you can set yourself up for success by keeping your goals in mind and giving yourself a fair chance.

Visible Hands is an early stage, pre-seed investment firm looking for men and women of color to provide meaningful capital and hands-on support. Visible Hands is a 14-week virtual-first accelerator with the mission of highlighting and investing in the limitless potential of underserved founders. Visible Hands helps founders build exceptional technology startups by providing meaningful funding, personalized support, and social capital.

Learn more: Daniel Acheampong, Visible Hands VC

Chris Jordan, Maxim Partners, LLC

If you want to start investing, Chris says that the best way to learn is by doing. Some early-stage investors start by working for a private equity firm, yet Chris affirms that there are other, more viable opportunities to gain experience. Being proactive rather than waiting for an opportunity to present itself is essential for growth and development.

Maxim Partners’ mission is to improve people’s lives through education and wellness innovation. They accomplish this by collaborating with entrepreneurial leaders who are looking for more resources to help them achieve their goals. By leveraging decades of experience, operational expertise, and extensive networks, Maxim Partners is a catalyst for meaningful and positive change.

Learn more: Chris Jordan, Maxim Partners

Will Porteous, RRE Ventures

Will compares investing in and growing businesses to the creative process. As an entrepreneur, you must allow for flexibility and time, just as you would when creating a work of art or writing a good story. Every entrepreneur builds a successful company in their own unique way, just as no two painters approach a canvas the same way.

RRE Ventures has grown to be one of New York City’s oldest, largest, and most active venture capital firms over the last 28 years. RRE has withstood the test of time because of a single guiding principle: change is the only constant. The firm has a decades-long history of working through multiple market cycles, across a wide range of industries, and with an ever-expanding stable of experienced and new entrepreneurs.

Learn more: Will Porteous, RRE Ventures

Mark Zorko, Brentwood Advisory Group

At first glance, Mark’s major success tip appears counterintuitive: Focus on failure. He claims that it is too easy to get caught up in success stories, so when failure strikes, many are unprepared. Over 50% of early-stage investments fail, so learning from others’ mistakes can help you navigate your own or even avoid them entirely.

Brentwood Advisory Group works with executive leadership to manage change, identify and implement solutions, and create opportunities on both the top and bottom lines. Brentwood Advisory Group provides a wide range of services, including M&A due diligence/integration leadership, interim executive leadership, Board of Director support, and turnaround and change management.

Learn more: Mark Zorko, Brentwood Advisory Group

Mark Thomann, Spiral Sun Ventures

Mark says it isn’t enough just to throw money at someone when investing in a business; you also have to be passionate about it. Mark advises others to wear a founder’s hat and be more than money — be part of the team. You should be present when your team is falling, not just when they are as successful as you want them to be. Adopting a mentorship role and truly being a team member will result in more success for everyone.

Spiral Sun Ventures is a seed capital fund that invests in companies that make better-for-you consumer products in order to promote a healthier lifestyle. Spiral Sun believes that health and wellness are critical for both people and the planet. They are strong supporters of conscious capitalism and seek opportunities to support minority and women-owned businesses.

Learn more:Mark Thomann, Spiral Sun Ventures

Dan Gaertner, DocuPhase

When purchasing a business, Dan suggests you get a good sense of its culture. Any successful acquisition necessitates a thorough understanding of the culture in order to determine the right people to retain. You can use a company’s culture to guide a smooth acquisition process if you successfully analyze it.

DocuPhase provides enterprise automation software and services. Their platform includes everything a company needs to carry out its digital transformation, process improvement, and growth strategies. They specialize in automation. The DocuPhase team is motivated by innovation, problem-solving, and making customers’ workplaces better. Their mission is to work with clients to deliver innovative solutions that automate and simplify the workplace while providing unparalleled customer service.

Learn more:Dan Gaertner, DocuPhase+