Month: November 2023

From launching her career as a trader to becoming an entrepreneur, Marisa Ricciardi has combined her in-house and agency experience with her capital marketing, financial services, and marketing acumen to build a successful business, The RicciardiGroup (RG). On this episode of “The Cred Podcast,” host Mack McKelvey and Ricciardi discussed Ricciardi’s approach to decision-making and why it’s paramount for leaders to understand the value that each decision carries so they give it the appropriate amount of rigor, deliberation, and consideration. 

Ricciardi shared how she has adapted her decision-making style as a business owner, relying on her trusted team and outside counsel to provide their expertise and help her “see past corners that she may not be able to on her own.” Additionally, Ricciardi talked about building her team to augment her own decision-making style, as these diverse approaches lend themselves to stronger, more favorable outcomes.

Keep reading to learn how Ricciardi differentiates her approach to decision-making based on the situation, how she’s learned from mentors on leading a team during a crisis, and how she filled a unique market need with her business.

Filling a Market Gap for Highly Regulated Industries 

Starting her career as a trader at a mutual fund, Ricciardi’s role evolved into what is traditionally known as back-office marketing. Because she acutely understood what clients needed, she became entrenched in working on the fund’s acquisitions and communications before joining other large companies in a hybrid finance-marketing capacity. From there, she spent a number of years working both in-house and at agencies where she was involved in capital marketing, financial services, and marketing.  

Nearly 10 years ago after having her first daughter, Ricciardi went out on her own and started her business, RG. Despite only being on the agency side for a handful of years, Ricciardi identified a market need that her business could uniquely fill.

“Being the client for all those years, I saw a need for agencies to be both creative and strategic in [solving your] business problem,” she said. “We’d have amazing agencies but it’d take such a long time for us to explain to them about business or our products, so I wanted to create a firm where that didn’t happen.”

And so, RG came to fruition and continues serving B2B clients in highly regulated industries, like fintech, insurance, and more. As the company has grown, so has the team. RG has 25 full-time team members and 50 partners.

“These partners are not just freelancers, but true partners that we’ve worked with throughout the course of RG,” Ricciardi said. “This allows us to be a deliberate, lean, strong, and mighty team that can flex up and down as needed. We actually call it the ‘RG Multiplier’ where we can add on to projects to custom create the right team for the right assignment.”

Getting Methodological for Bigger Decisions 

Reflecting on her career working in fast-paced, highly regulated environments, Ricciardi noted that she generally made decisions based on where she could thrive, grow, move quickly, and learn. Now as a business owner, however, she has shifted her approach.

“I also am more methodical [in my decision-making],” she said. “Like I say to my daughter,  slow down and think about it more carefully. I wasn’t necessarily able to do that in my previous roles. You’re making decisions and you’re moving so quickly that you’re not actually thinking through the decision tree of ‘what are the best outcomes?’”

As a business owner, she relies on decision trees to help her navigate the potential outcomes associated with different paths and determine what will generate the optimal results for her clients, team morale, and her company at large. Collaboration with fellow trusted leadership is also an important part of Ricciardi’s decision-making process. She cited a philosophy around cognitive decision-making that focuses on three pillars: feeling, thinking, and acting.

“I tend to think and then act. I am lighter on the feeling side, so I’ve hired my team to augment different parts of that triangle,” she said, adding that RG has team members take Strengthsfinder assessments to see how their strengths and skill sets complement each other. 

“For important business decisions, we’ll have someone like my CEO at the table who is super analytical, full of empathy, and may approach a problem completely differently [than I might],” Ricciardi said.

Evaluating Decision-Making’s Value-Cost Equation 

When it comes to smaller decisions, Ricciardi tends to deploy a different approach due to the limited number of hours in each day.

“For those smaller decisions that don’t require as much deliberation, we move quicker,” she said. “I always say to my team and myself that, ‘I’d rather we make a decision and have that be the wrong decision than be stuck and never made a decision at all.’”

The higher costs decisions require more research and conversation whereas you can make lower costs decisions at a much faster clip.

“If I was evaluating whether we want to continue with our office space, that is a really high-cost decision and we would need to do a lot of digging into the data,” Ricciardi said. “But, if we’re looking at what days of the week we’ll be in the office, that’s a medium-value, low-cost decision where we can move a lot quicker.”

Using Your Network to Weigh Your Options 

Both Ricciardi and host McKelvey had similar experiences in that they have not had any formal decision-making experience, which is common among most executives and leaders. Rather, they’ve modeled their decision-making after bosses and mentors whom they’ve admired. 

“I’ve had great bosses and mentors who I’ve emulated more and I’ve found my own style that works for me,” McKelvey said. “But, I especially watched how they approached major crises and how they rallied people together. I saw how they took external input and matched it with some of their own [gut feeling] to reach that final decision.”

Ricciardi echoed this sentiment, saying that she has emulated many of her mentors and leaders as she navigated the workforce during challenging times from the 2008 financial crisis to COVID and beyond. 

“As a marketer and a communicator, you’re making different decisions that you’ve never had to make before,” Ricciardi said. “Now running my own business during these macro and micro issues, I’m leaning in and leading the team based on what I’ve seen from previous leaders and bosses at my other firms.”

When it comes to leading and decision-making in tough times, Ricciardi champions leaning on outside counsel whether that’s board members, therapists, or business coaches.

“Getting that outside perspective is helpful, especially working in an intense city like New York,” she said. “They can help you make sure that you’re on the right track or can help you see around corners that you yourself can’t see.”

When Outcomes Hang in the Balance 

Many decisions, even the ones with unfavorable outcomes, present a learning opportunity according to Ricciardi. The RG, for example, has been involved in a large RFP and as the founder and CEO, Ricciardi had to weigh the pros and cons of her team diving all into the pitch as it could detract from their creative and strategic efforts with the agency’s current clients. 

“I decided that we wouldn’t start the project until I knew that it was the right opportunity for us,” said Ricciardi. “What that meant is that we wouldn’t participate in tissue sessions or some of the other things that agencies were doing because it would be more costly.”

In the midst of the process, Ricciardi reflected on this choice and noted that her tactic may cost them the business in the end.

“Maybe by the time this episode airs, we’ll know if we won the RFP or not but I stand by my decision even if the outcome is favorable or not,” she added. 

One recent decision that Ricciardi firmly stands behind is turning away business that didn’t align with her and her business’ core values. The prospective client treated RG more like a vendor, versus a partner, propelling Ricciardi to decide not to work with them. 

“Truthfully, it was a very profitable piece of business and we did lose revenue during a difficult financial market,” she said. “I was really torn [by this decision], but ethically, I look back now and I am glad I made that decision because I think it was the right one.”

Listen to Marisa’s full episode here.

Serial entrepreneur, startup operator, and angel investor Shereen Shermak joined host Mack McKelvey on “The Cred Podcast” this week to discuss all things decision-making, angel investing, and more. Shereen, a Boston tech luminary, is now an active angel investor dedicated to diversifying her portfolio and paying it back to traditionally underfunded groups.

With an active personal stake in nearly 80 early-stage startups, Shereen shared why she loves the chaos of startups, or as she put it, making the chaos productive. Mack and Shereen discussed everything from prioritizing your values in decision-making to raising a red flag when needed. Continue reading for tips to make stronger decisions, from the ones that impact your day to the ones that impact your organization, and beyond. 

Intentionally Paying It Forward

From her early career roots to being a serial entrepreneur, Shereen is dedicated to paying it back. She’s mentored and worked to elevate up-and-coming professionals, underrepresented groups, and even small business owners. After 9/11, she felt the need to do something to help, leading Shereen to get her second Master’s degree at Harvard. Fondly referring to this position as the “most important job she’s ever done,” Shereen worked for the City of New York under the Bloomberg Administration to help small businesses survive the economic uncertainty.

Over the past several years, Shereen has offered guidance to aspiring and current entrepreneurs at Harvard Business School. In January 2019, Shereen co-founded TBD Angels, a Boston-based group of like-minded passionate angel investors assisting talented entrepreneurs through advice, connections & capital. TBD Angels started with a group of six to eight older who were frustrated with the lack of investments in Boston, which Shereen noted has a history of having “tightly cold wallets.” Now almost four years later, TBD Angels has expanded to a couple hundred people and a fully operational team. 

As she’s invested more in various businesses, she’s also become more dedicated to diversifying her portfolio.

“I feel that it is my social obligation to put some [capital] back into the ecosystem and help somebody else move ahead, But if I’m honest, having a diverse portfolio wasn’t always a conscious part of my investing,” she said. “I was looking for the best deals. Then, I started questioning why it is so hard for traditionally underfunded groups to raise capital.”

Over the years, as investors, Shereen and TBD Angels have placed greater emphasis on working with a diverse set of entrepreneurs and recruiting women and people of color into the group, with Shereen adding, “We want the people we work with and the investments to look like the community we live in.”

With personal stakes in many early-stage startups, Shereen has played an active role in advising and filling in where she can be helpful. 

“I think it’s appropriate to help those [early-stage] companies when I am writing individual checks,” Shereen said. “I see where I can help until that next funding round comes and I feel it’s the right point where [I] can get off the bus.”

From Startup Product Manager to CEO & Co-Founder

Shereen’s startup career took off in 2007 when she moved from New York to Boston. Jumping into the fintech space, Shereen worked at a startup as a product manager for a few years where she could get into the weeds. By understanding how a startup operates, Shereen could then share these learnings with up-and-coming talent interested in diving into the startup world.

“If young people ask me about this space, I tell them that startups with Series A or B funding are good entry points,” she said. “While they’re still figuring a lot out, they’re specialized and have a product management team that is usually separate from marketing.”

Armed with this experience and knowledge, Shereen went on to become the CEO and co-founder of numerous companies including her most recent company, Stealth. As a co-founder and leader, Shereen noted she is a firm believer in focusing on where she specifically can drive value. At Atlantic Quantum, a developer of scalable quantum computers, she found she could take what she learned from her startup experience to make this business successful.

“A lot of those skills were transferable so I found areas where I could be most useful like in operations,” Shereen said, adding that 50% of a startup’s success comes from building out the operations. “That’s always been my goal if I join a company full of scientists. They can do the science, and I can worry about where the money’s coming from and focus on execution.”

Getting into a startup at the beginning stages excites Shereen, who said that she usually starts from an idea on a piece of paper or technology before building a functioning and ultimately successful company.

“I enjoy those first two years of trying to take the chaos out of the equation or, at least, make the chaos productive,”  Shereen shared. “And then, I’m moving on to the next thing.”

Making Decisions, Confidently 

As a leader, you’re constantly making decisions, many of which impact your entire company. Often, many startups early in their inception don’t have a solid framework in place to approach important decisions. Rather than coming with a framework as soon as you get in the door, Shereen advised leaders to get to the heart of your company’s values and learn how your business makes decisions formally and informally.

“When you establish your values at the beginning, decisions are much easier down the line,” Shereen noted. 

She explained for TBD Angels, if they’re deciding that they are trying to support certain investment types, then that should be reflected in the deal flow. They monitor these investments and report on them regularly to ensure they align with the group’s values. 

“Everybody cares a lot about it and they joined the group because it was consistent with their values,” Shereen said.

In addition to knowing your values, Shereen emphasized the importance of being open to new possibilities. Unlike older generations, younger professionals explore many careers and companies throughout their careers. 

“When deciding what you want to do with your life, realize you’re not making a long-term commitment,” she said. “Try things out and see where you fit in. I’ve had three careers: environmental engineering, finance, and now, startups. I’m sure I’ll have a fourth but I don’t know what it is yet.”

Gamifying Decision-Making

For day-to-day decisions, Shereen likes to game it out with a framework that she used when she was a data modeling and decision analysis teaching assistant. Essentially, she used decision trees to map out the options and their potential risks, assigning each a weighted score. She then looked at the odds that something will happen, and assessed whether or not she felt like she could change those odds. 

 “That can be helpful to guide you through a broad volume of decisions, or those micro decisions. But, when it comes to personal and life decisions, it’s about understanding your values and if the next thing you’re going to do fits those values,” she said. 

For Shereen, she only has one role that she felt was not the right call and that was because it failed to align with her values. She wasn’t necessarily thinking of her family or herself when making that decision, which was why it was problematic. 

“It was more about what’s gonna look better on my resume. And to me, that’s ironic because I feel like that’s what most people spend their time thinking about in terms of showing career progression and that hasn’t worked for me at all,” Shereen said. “I have had a zigzaggy career and that’s worked out much better.”

Use Your Red Flag, Intelligently & Sparingly 

Not every decision goes according to plan and while we don’t have a crystal ball into what will work, leaders may have a strong inkling that something won’t reap success. Whether you’re the CEO, a manager, or a startup specialist, Shereen said you should raise that red flag, but do so sparingly. When it comes to these red flags, Shereen is referring to decisions that could threaten or negatively alter your company.  

“Be explicit about those red flags and don’t use them frequently as they can be very powerful. The sky can’t fall every day,” Shereen said. “When someone told me about their thinking that was different from what I would have done, I could see the passion and thought behind it. It changed my own thinking and had a productive outcome for this startup.” 

To round out the conversation, Shereen shared her plans for the next couple of years, like doing fractional C-suite work. 

“I like the mix of having multiple engagements that I am juggling and the context switching,” she said. “I’m at the point in time where I know how to do what I want to do, so I can do it more efficiently.”

This conversation is bound to be one of many on “The Cred Podcast,” and we look forward to continuing to learn from Shereen as a decision-maker, startup leader, investor, and overall person. 

Listen to Shereen’s full episode here.