Meet The Female Leaders Of Finance: “Knowing when to sell an investment is important” with Margaret Montague and Jason Hartman

Jason Hartman
Oct 31, 2019 · 13 min read

Knowing when to sell an investment is important, even if the timing means leaving some “perceived value” on the table. I have seen entrepreneurs delay bringing in external investment partners until they feel they can maximize their liquidity and/or achieve the “right amount” for retirement. They miss the fact that while they are trying to grow their business without investment capital or valued-added partners the world can pass them by. While these entrepreneurs wait, better capitalized competitors can become the sector leader — and some sectors do not have room for second place. By not selling a portion of the business at a (perceived) “lower valuation,” owners can hurt the longer term growth prospects of their businesses and valuation.

As a part of my series about strong female finance leaders, I had the pleasure of interviewing Margaret (Meg) Montague, Senior Managing Director, The McLean Group. Ms. Montague is an investment banker with nearly 20 years of experience. She has completed nearly 40 engagements across a broad range of industry sectors with a particular focus on franchise and multi-unit concepts, consumer, healthcare, business services, and manufacturing. She has completed transactions involving prominent franchising companies including Outdoor Living Brands (Mosquito Squad), RiseMark Brands (Right at Home and IKOR), Frost Management (Planet Fitness area developer), Excel Management (Planet Fitness area developer), Fun Brands (Pump It Up and Bounce U), Express Oil Change & Service Center, Massage Envy, Jan-Pro, Comfort Keepers, ReBath, Cookie & Associates (Great American Cookie and Pretzelmaker franchisee), and Westward Dough (Krispy Kreme franchisee), among several others. Prior to joining The McLean Group, Ms. Montague was a Director at Fidus Partners and Edgeview Partners, both middle market investment banks, where she provided merger & acquisition advisory services. Ms. Montague started her career at Morgan Stanley in New York City where she spent nearly six years working on mergers & acquisitions and equity and debt offerings primarily for healthcare and consumer companies. Ms. Montague received a B.S. with a concentration in finance from the McIntire School of Commerce at the University of Virginia and an M..B.A. from the Darden School of Business Administration at the University of Virginia. She is a FINRA Registered Representative (Series 7, 63, 79).


Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Banking/Finance field?

As a first year undergraduate student at the University of Virginia, I thought I either wanted to pursue a premedical curriculum or a business degree. After taking several prerequisites for the undergraduate business program, I decided finance was the field for me despite questions about where that degree would lead me. I grew up in a family of doctors, so I understood that path; however, I had no understanding of the business world. Once accepted into the UVA McIntire undergraduate business program, I soon realized my classmates were extremely competitive and already charting pathways to future jobs.

Being competitive myself, I wanted to secure the best opportunity I could. I “jumped before I looked” and ended up in a sea of hungry students searching for investment banking opportunities in New York City. While I had good grades and the right academic pedigree, I had focused my summers on international travel rather than securing high-profile internships. Thus, my resume was fine but not as compelling as some of my classmates. I also had zero connections and relied on cold outreaches with whomever would respond to my calls or emails.

Ultimately, I secured several interviews on my own. However, a dear, thoughtful friend who had just landed her dream job still had a very coveted interview slot with Morgan Stanley. She deleted her name from the interview list, inserted mine and told me when to show up. I felt as though I had no real shot of progressing beyond the first round. After all, Morgan Stanley did not even have my resume. But, instead of feeling defeated, I felt I had nothing to lose. As a result I was less stressed, more confident, and said what came to mind in the interview. I not only progressed to the second round, but I was invited to the final round interviews in New York City! Ultimately, I accepted an analyst position in Morgan Stanley’s investment banking division, where I remained for three years prior to going back to school for my M.B.A. I returned to Morgan Stanly after business school for another three-year stint as an associate in the M&A group. It was an amazing, valuable experience.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

Three months after starting work, I was assigned to an engagement involving a pending IPO. I accompanied the management team on its roadshow over the next three weeks. The first leg took us to Europe, and we traveled to Zurich, Amsterdam, and London. As we wrapped our last meeting in London, we headed to the airport in four different chauffeured cars. I was in a car with the CFO and most of the other travelers’ luggage. Traffic was suddenly at a standstill, and we were booked on the last flight out of Heathrow to JFK. Worse still, we had a full slate of meetings the next day in Philadelphia and I held the presentation materials.

Back in 1996, cellphones were not prevalent, paper airline tickets were in use, and airport security was far less strict (thankfully!). I did, however, have a rented international cellphone with limited service. I called Morgan Stanley’s travel department to let them know we were likely going to miss our flight.

My car arrived at the airport some 15 minutes before the flight was scheduled to depart. The CFO and I loaded all of the bags onto the worst carts ever made and sprinted for security. We tossed bag after bag onto the conveyor belt and collected them on the other side. We loaded them on more carts and sprinted to the gate.

When we arrived at the gate our seats had already been reassigned. I felt defeated. Just then a gate agent approached and told me the rest of the team had made the flight and they needed our coveted “black box” with the management presentations and slide wheel for the meetings (yes, a slide wheel with actual slides). I handed it over.

After some furious typing on the computer, another gate agent looked up with a smile. In a wonderful British accent he said, “I have two seats on the Concorde for you.” It left 30 minutes after our original flight and landed three hours before. He briskly took all of the bags, sealed them in oversized plastic bags, checked them on the Concorde, and ushered us to our seats.

We were wined and dined for the next three hours. Needless to say, the rest of the management team thought they were “seeing ghosts” when we met their flight at JFK. Lessons learned: Some travel stories do end well, and always be nice to airline employees.

Are you working on any exciting new projects now? How do you think that will help people?

Exciting is a relative term in the investment banking world. Nonetheless, I do feel a great sense of excitement working with entrepreneurs and helping them recognize the greatest value from the businesses they have created. I have done a lot of work over the last few years with Planet Fitness franchisees. Most were once struggling gym operators just trying to survive until they saw the benefit of converting to the Planet Fitness model. Now, by being engaged by these franchisees to bring in sophisticated investors, we have helped them accelerate their growth potential, expand their infrastructure, and realize tremendous liquidity. We have helped them monetize their life’s work and realize values for their business that have been far in excess than they ever thought possible.

What do you think makes your company stand out? Can you share a story?

Across my career I have worked for a number of firms. Some were big; others were small and growing. All shared one thing in common: rigid control over the deals bankers could entertain. At The McLean Group, the franchising team has the latitude to work on any franchising deal we want to pursue, regardless of size. As a result, we have been able to work everywhere on the continuum from deals that were small and entrepreneurial, but with tremendous growth potential, to deals with very large national franchisors. Our client prospects are not limited by the need to meet budget requirements or executive dictums. As a result, we can select to work with clients with whom we relate and have businesses that are meaningful. This kind of flexibility is exceptionally rare in the investment banking world. For example, I am currently in discussions with a very small, relatively new franchisor concept. This engagement will not be a “big” one for The McLean Group, probably $10 million at most; however, we are passionate about the concept and simply love the founder and owner. If I were working for any of my prior firms, this deal would never be approved for engagement. The McLean Group allows me to be less transaction-minded and instead work on deals that stir passion and excitement.

Wall Street and Finance used to be an “all-white boys club.” This has changed a lot recently. In your opinion, what caused this change?

Women’s growing presence in finance, and the successes they have achieved, is the impetus for change. These talented women have entered this male-dominated world equipped with knowledge and ambition and disrupted the status quo. In turn, these successes have made once stodgy organizations value women’s minds and the unique perspectives they bring to the workplace. Companies also recognize that more and more female business owners comprise their client base. They find that female bankers often relate better to this new generation of entrepreneurs.

Of course, all of this is prefaced by women wanting to pursue business degrees and enter the fields of finance and accounting. Greater acceptance of women, especially to investment banking internships, has translated to more opportunities to demonstrate their work ethic, thoughtful approaches and organizational skills. As women have risen to management levels, they have opted to mentor the next generation. At the same time, many women have come to realize they can do it all, if they choose to do so. Not so long ago, some women felt they had to leave their career to raise a family. Better childcare options, benefits, flexible work schedules, and supportive partners have aided the transformation and allowed women to stay on their career paths uninterrupted.

Of course, despite the progress, we still have a lot more work to do to achieve parity. According to in CNBC, less than 17 percent of senior positions in investment banks are held by women. In your opinion or experience, what 3 things can be done by a) individuals b) companies and/or c) society to support this movement going forward?

The issues the U.S. Women’s National Soccer Team are vocalizing now speak volumes about parity in the workplace today. Society, I suppose, must legislate to assure women have a legal basis for confronting the inequities that continue to persist. Society, too, must assure equal educational opportunities and assistance exist for all, as knowledge is the key to everyone’s success. Last, society must act decisively in pursuing legal remedies when individuals or organizations harass or otherwise display bias against women.

Companies must offer flexible work schedules and be open-minded to alternative work environments and telecommuting options. They also can assist with benefit packages that include better maternity leave policies, privacy rooms, and subsidized daycare or even on-site daycare facilities. Of course, compensation parity and equal advancement opportunities are paramount.

Individual women need to use their voices. They need to ask for that raise or question why they are making less than a male with less experience and education. Silent acceptance is no longer an option. Women, too, need to leverage opportunities that expand their knowledge and diversify their experience. Last, but not least, women must network like men do. Women tend to toil at their desks while men are making deals on the golf course, over lunch, or during happy hour. Women need to recognize that social and professional gatherings are important components of getting ahead and sometimes more fruitful than working through the lunch hour or staying late at the office.

You are a “finance insider”. If you had to advise your adult child about 5 non intuitive things one should do to become more financially literate, what would you say? Can you please give a story or example for each.

1. Do not take on more debt than your cash flow can support, even if someone is willing to lend you the money. The Great Recession illustrated the pitfalls companies with too much debt faced when covenant-light debt deals were commonplace. Many simply could not sustain their cash flow to service that debt and went out of business.

2. A dollar today is worth more than a dollar tomorrow. Based on the time value of money, having a dollar in your bank account today can be worth more than having that same dollar several years from now. I worked with a client who had very attractive offers to sell his business. During the process, he materially missed his budget, which spooked the buyer. The buyer lowered the purchase price based on where the baseline earnings were tracking. My client decided not to consummate the deal based on his confidence in future business earnings. Fast-forward one year. His business earnings were even lower than the buyer projected. Due to future uncertainty, monetizing an investment today is often more valuable than doing so over the long term.

3. Pigs get fat, hogs get slaughtered (i.e., don’t be too greedy). Knowing when to sell an investment is important, even if the timing means leaving some “perceived value” on the table. I have seen entrepreneurs delay bringing in external investment partners until they feel they can maximize their liquidity and/or achieve the “right amount” for retirement. They miss the fact that while they are trying to grow their business without investment capital or valued-added partners the world can pass them by. While these entrepreneurs wait, better capitalized competitors can become the sector leader — and some sectors do not have room for second place. By not selling a portion of the business at a (perceived) “lower valuation,” owners can hurt the longer term growth prospects of their businesses and valuation.

4. Cash is king. While there are many large, sexy businesses at “unicorn valuations” that have negative earnings, ultimately, cash will matter eventually. Having worked on Wall Street during the IPO “dot-com” era, you learn that earnings and cash flow matter more than “eye balls” for long-term sustainability.

5. Know your equity partners (partners in general) and be careful to legally document your financial and business relationships with them. I have seen many entrepreneurs who took on equity partners/investors they did not know well and/or with whom they did not document their business/investment relationship. Such investors can be a nightmare when the time comes to sell the company.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am grateful to my first boss at Morgan Stanley. He definitely took a chance by bringing me into his financial execution group, as we had never even met until my first day on the job. His only knowledge of me was on paper.

At first, the thought of working with companies going through the IPO process did not excite me. It turned out to be an amazing experience, more so than I ever could have imagined. I traveled to some great places and worked with some outstanding management teams. More important, my boss was a wonderful mentor who was honest with me about my shortcomings, celebrated my victories, and was very thoughtful about teaching me. He truly took me under his wing and developed me as an early professional. Even more important, he helped boost my confidence and my career.

When I thought about leaving his group along with some peer analysts, he encouraged me to stay another year and train the group of incoming analysts. When I agreed, he assigned me responsibility for tasks beyond my job title. He was very trusting in my capabilities and somehow knew that if he let me fall, I would find a way to fly. For example, we were working on an offering for an already publicly listed company. He gave me total responsibility for reviewing the offering memorandum, checking and cross-checking the content, and assuring it complied with Morgan Stanley’s strict style guidelines. Normally, someone far more senior than I would have been given this responsibility. I succeeded in producing an accurate prospectus in spite of my own self-doubt. This early success opened the door to other benefits such as getting first choice on new deals and being trusted as a more senior, go-to associate on IPOs.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My life lesson quote is “Always have a means to take care of yourself.” While not a quote from a book or famous person, it is a piece of wisdom a college professor conveyed during one of my business classes, and it has stuck with me to this day.

He was speaking frankly to female students as the father of two young girls. He encouraged us to always have a path to a career, even though many of us might choose to be stay-at-home moms. At age 22, I did not appreciate just how uncertain life could be, but that was his point. Perceived safety nets can disappear in a moment. So, in case the “bread-winner” in your life should disappear, you should always have a “pivot strategy” and/or an on-ramp to a job.

Today, I know firsthand how invaluable his advice was. My brother passed away at a very young age leaving behind three children and a wife. She was able to carry on because she had a pivot strategy. After being with my first spouse for 15 years, he disappeared from the relationship. Having a career enabled me to take care of myself financially. Now, remarried with two children, my career contributes to our household needs and future retirement. It also stands as a safety net against any future uncertainty.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. :-)

I am passionate about education. I would inspire a movement that assures that children have access to early education (pre-K) and free or affordable schooling throughout the college years. I would also want adults to have access to affordable education. Education is integral to success in life and the on-ramp to career advancement or new career paths. And, as pointed out above, it also provides a pivot strategy should life’s unpredictable nature throw you a curve ball.

Thank you for all of these great insights!

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Jason Hartman

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Author | Speaker | Financial Guru | Podcast Rockstar

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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