Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur“ we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Shawn Sweeney.
Shawn Sweeney is the founder and managing partner of Spinnaker Consulting Group.In his 14 years as an executive with a Fortune 200 financial services company, Sweeney led a variety of organizations, including Strategy and Analysis, Operations, and IT. He was often called on to spearhead turn-around situations or develop and build new organizations. Today, he leverages these experiences to help his clients meet the changing demands from customers, regulators, and competitors.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Shawn Sweeney: As a high school student, I was very interested in engineering and math, and my father and grandfather had served in the Army and Navy, respectively, so I had a family connection that opened my eyes to the military academies. I went to the U.S. Naval Academy planning to go into aviation, and I majored in aeronautical engineering. During one of my summers, I had the opportunity to serve aboard a submarine and instantly fell in love with the mission and crew camaraderie. Based on that summer experience, I selected to serve as a submarine officer once I graduated.
When I decided to leave my military officer career, I was offered the expected engineering-based roles from major manufacturers. Then this upstart financial services company came along, with an opportunity to apply my engineering skills — and, to a degree, my leadership experience — in a different way. It was still very much in startup mode at that moment, and it afforded me a chance to be part of a rapidly growing organization. The company promised it could teach me banking, and it did. After 14 years of taking on new roles and a diverse range of skills and experiences, it was time to see what could come next for me.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
Shawn Sweeney: I was looking to flex new muscles while leveraging my deep experiences in the banking sector. Having worked with consultants at nearly every juncture, I recognized a gap in the existing model, somewhere between pure strategy development and then leaving the client to figure out how to execute those ideas. I saw a place where we could provide clients with industry experts (former banking colleagues) that could deliver pragmatic solutions and measurable results. It’s a mindset that moves away from racking up as many billable hours as possible to a people-first mentality where we collaborate with clients to drive their business goals.
This need hit home for me because, during my time in the financial services industry, I’d hired plenty of consultants, and two things always bothered me. First came a sort of bait-and-switch dance, where we’d talk with a senior account manager with deep experience, determine we had a match, and sign an engagement. On the first day of the assignment, the junior varsity squad walked in the door with no firsthand experience, only the knowledge of what the textbooks they’d just walked away from told them. Secondly, too many consultants wanted to focus on the big idea and how to solve a problem, even though we were the experts on our own business. The greater need for our team was in actively delivering on ideas, rather than generating them.
I knew there had to be a better way, and that became the genesis for Spinnaker.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Shawn Sweeney: On the surface, I’m not sure I’d call myself a natural-born entrepreneur, but I’ve developed the skills along the way that have contributed to my ability to lead. I’m a quick learner. I’m confident I will figure things out. And I reach out to people with expertise that can help me grow.
For example, consider my tenure as a U.S. Navy officer: I was learning the tools to become an effective leader and strategist, while also being expected to follow the orders of my senior officers. I went from that very structured military world to a financial services company that empowered its people to dream big and pursue out-of-the-box ideas.
Today, I bring a bit of both experience as an entrepreneur. Since starting Spinnaker, and identifying new market needs, we’ve added a sister organization in Flying Phase, which we launched last year at the start of the pandemic. This was a logical outcrop of the work we do at Spinnaker, creating a specialized team with the technical skills to create sophisticated big data, machine learning, and AI ecosystems for organizations looking to up the ante on their analytical firepower.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
Shawn Sweeney: My wife, Lauren, started her strategy-based marketing agency, Dotted Line before I launched Spinnaker. I captured a lot of her excitement and enthusiasm as she figured out what this firm would be and how she navigated the challenges she encountered. Her experience illustrated how much different an entrepreneurial effort could be from the corporate environment we’d both become so familiar with. Lauren was a point of inspiration as she went out there and made that success happen for herself.
What do you think makes your company stand out? Can you share a story?
Shawn Sweeney: For the Spinnaker team, our client work is personal because we’ve been in our clients’ shoes. With that shared experience, their challenges are our challenges. Their problems are our problems. It’s part of a continuous cycle.
In fact, we consider our job to be to work ourselves out of a job. No matter what we are brought in to accomplish, we provide training so clients know how to fix something or do something the next time. We spend a lot of time coaching leaders and their team members. It’s not something we specify in the scope of work, but it’s the right thing to do. We are helping our clients get better, develop processes to change nimbly, and train others to follow suit. If we’re there indefinitely, the question becomes if we’re solving for the right or root issue.
As one client told us: “Consultants from other firms act like contractors; Spinnaker consultants act like teammates.”
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Shawn Sweeney:
Grit: In life, in general, you’re going to face obstacles. If you’re knocked down 1,000 times, you need to get yourself back up 1,000 times. If you think one-day things will get easier, then you shouldn’t be an entrepreneur. There’s always something better on the other side of the wall, and you need to work for it as that target moves. When I first opened Spinnaker, we were pursuing an opportunity with a business that I had previously helped when I was in a temporary role with another consultancy. That consultancy tried to claim I would be violating my non-compete clause, but I knew this opportunity was outside those terms, so I dug my heels in and refused to yield. Eventually, that door opened — and we won the engagement.
Teachable: No one will ever have all of the answers, and I have the humility to recognize where I need to learn more and lean on others to help guide me. Look at professional football players, for instance: Of course, they have a head coach, but they also have a position coach, a strength coach, an offensive or defensive line coach, and more. While I continue to evolve and add to my core skills, one of the things I’ve been working on with one of my mentors, Tommy Thompson, is around the real need to create space for critical thinking. This is a set-aside time where I’m not actively working on a concrete deliverable, but instead thinking and reflecting on where we’ve been and how we will continue to move forward. I’ve got time blocked on my calendar every Wednesday morning — no meetings or calls allowed — to do just that. While it might seem counterintuitive, this open time is the simplest step business leaders can take to invest in their business.
Flexible: The business world is changing so fast. Even if you think you understand market needs, that’s going to be different by the time you get there with your product or service. You need to be flexible to adapt at the moment and not feel obligated to follow every step in your original plan when signs are pointing you in other directions. In our daily work, we continue to flex our service offerings. We develop an idea for what we think our clients might want or need, but then as we take that idea to market, our clients often refine or reshape the idea. We have to remain flexible to ultimately meet client needs — and not stay wedded to the original idea.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Shawn Sweeney: Many people told me to focus purely on growth and business scalability — and to not get too hung up about the people you are hiring. In reality, you need to be willing to make the right investments upfront. Hiring the right people and setting the right culture, in hindsight, is the №1 job for the CEO of a startup. Get those things wrong, and you’ll be dealing with the consequences for a long time.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
Shawn Sweeney: That all starts with culture. When I began to consider what Spinnaker could be, of course, I dedicated the appropriate research and planning to develop a comprehensive business plan that detailed our offerings and identified potential clients that needed the types of services we would deliver — basically the “what” part of the equation. But I didn’t shortchange my investment in shaping the foundation of “why” we’re here. That’s woven into who we hire — proven experts in their fields — and empowering them to contribute at the top of their game.
As a leader, if you believe that there is more to life than work and that both matter, then your people will embrace that as well. If you’re a CEO working 80 hours a week, then your people will be obligated to do the same — especially if they want to climb the ladder. You need to understand what is important and what makes each person in your organization whole, beyond a meaningful paycheck. Use those insights to refine your organization — if there’s a shared community cause, find opportunities for volunteer hours or monetary matches. Be flexible for parents to take time to participate in their children’s sports, academics, and other extracurriculars. Encourage programs that support your people’s fitness and mental health.
We believe in taking care of our people. Our people take care of our clients. Our clients ultimately take care of our company. It’s a virtuous cycle that keeps people at the heart of everything we do.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Shawn Sweeney: You have to deliver on what you say. After all, people don’t hire consulting firms; they hire people. And they can’t trust someone until they know them, so you are building a relationship from your first contact point. Act with honor and honesty, two important things that were underscored in my military training. People — whether they are your employees or your customers — need to know that you are serving their best interests.
Can you help articulate why doing that is essential today?
Shawn Sweeney: As consultants, we have to influence people to take action, which often means stepping out of their comfort zone and doing something different. If you don’t have a trusted relationship, you can’t effectively guide your client in making the right decisions for their business. Demonstrating integrity in your operations and acting with grace will translate into respect and loyalty that will enable your business to thrive and succeed. To me, it’s a simple matter of doing what’s right.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Shawn Sweeney: Our natural inclination is to look at profit and loss statements to assess the health of our business. The problem is that those metrics tell you what has already happened when you want to be looking for information for where your business is headed. That’s where your balance sheet comes in, as it gives you insight into your cash flow. Many profitable businesses have failed because they didn’t effectively manage cash flow.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
Shawn Sweeney: When you run your own business, particularly early on, every idea and every action matters. If you have 10 employees and make a bad call on the business or product, you might not only have to let those people go, but you might lose your company. In a corporate job, you’re probably working with a larger organization, with the maturity and risk structure that one wrong decision by one person won’t have the same worst-case consequences.
But there’s nothing like it when your entrepreneurial venture is hitting its targets. You’re celebrating a pretty major high. It’s the flip side of that same coin: That success is happening because of the decisions you made.
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
Shawn Sweeney: Getting our first $1 million contracts signed was a milestone moment. That level of investment demonstrated a client believed in us and what we were doing. You could see the excitement on every team member’s face, and you could feel a shared sense of accomplishment. This was a team victory, as every consultant here played an important role in making that happen.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
Shawn Sweeney: In the early part of the pandemic, the financial industry — indeed, all industries — paused and even took a step backward as it figured out what to do until our global economy stabilized. With a consultancy focused on banking, of course, I worried about this interim moment as 50 families counted on this organization to put food on the table and send kids to college.
Based on your experience can you tell us what you did to bounce back?
Shawn Sweeney: We realigned our work to double down on business development and remained true to our people-first values as we navigated into an even stronger position today. This is the moment where you demonstrate resiliency. For us, it was remaining clear on our purpose.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
Shawn Sweeney:
Continue to Learn: At Spinnaker, we require every employee — including me — to complete 40 hours of training during the calendar year. Each of us can decide what our training means: get the latest industry insights by attending (or speaking) at a national conference, take college classes to earn an advanced degree, or master a new coding language. This means we are continually elevating our skills and remaining the experts our clients expect us to be. Just because I opened the doors on this business nine years ago doesn’t mean I have all the answers, so I remain committed to keeping my eyes open to gaps in my own development and enhancing my tools and resources to continue to run a successful business.
Follow the Right Metrics: I’m growth-oriented, and that means I need to be looking at the right financial metrics. One of my favorites is our operating cash cycle, which is the time between making a capital investment and receiving payment from the end-user. This is the metric I rely on when determining our capacity for further growth.
Remember Why You’re Here: As consultants, we’re serving people. As part of the Spinnaker team, we’re here to make life easier for our clients, not create extra work for them. We always look for the most practical and sustainable solution. As we deliver that value, we find that clients come back to us with even bigger and deeper problems to fix. Why? Because we are trusted advisers who serve as extensions of their own teams: We put their needs first.
Have a Mechanism to Decompress and Disconnect: To me, entrepreneurship is more of a marathon than a sprint. You need an outlet beyond the office where you aren’t 100% consumed by the business. A few years ago, my wife and I discovered we each had the ability to take a week off each quarter from our respective businesses. While our immediate fear was that our travel (and absence from the office) would be a risk to our growing businesses, we’ve come to realize that the mental health respite from the daily grind has a largely positive impact.
Don’t Go It Alone: Find other people or a peer group that you trust with sharing experiences and asking for guidance. It certainly can be lonely at the top, as you work hard against countless pressures. Through a local CEO council, I’ve been able to reassess my challenges and find out they aren’t unique to my business. This group has become a sounding board and trusted peer resource.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
Shawn Sweeney: Resilience is the ability to pull yourself back up, perhaps when a strong wind has capsized your sailboat. You might not be immediately able to right the ship, but you know each step that needs to be done. And you try again. And again. And again, until the mast is pointed toward the sky once more.
As a company and as people, we all faced harsh conditions when the coronavirus swept across the nation last spring. That certainly took some of the wind out of sails for a moment, as we were all suspended in the early days, looking for a ripple on the water to see where the wind might blow next.
Then something amazing happened. Our people became each other’s own lifelines. On Slack, we saw our people offering words of encouragement. Then those with school-aged children started sharing tips for home-schooling. As consultants, we’re accustomed to working remotely, but before March 2020 that meant at the client’s worksite — not side-by-side with our school-aged children harrumphing when their technology wouldn’t work. But our people pivoted to find ways to apply all those great tips and strategies to help themselves and their families, and it changed how we work for the better. Resilient people not only are open to other possibilities, but they have the perseverance and persistence to track them down.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
Shawn Sweeney: Plebe year — your first at the Naval Academy — is brutal by design. To prepare the highest-caliber officers who can be resilient in the toughest battle conditions, the academy tries to break you down. Their objective is to make you fail, so they can see if you have it in you to pick yourself back up and go at it again. It’s a humbling experience, particularly when you consider that everyone there is a picture-perfect definition of an academy recruit: at the top of their high school classes, competitive athletes, and basically every leadership trait you could imagine. This is the first time for many to fail. All of us knew that, and we had to come to terms with rebounding after failure, including learning how to rely on our peers who ultimately would serve alongside us.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Shawn Sweeney: Nothing creatives a perspective like time in a submarine. When you’re 400 feet under the sea in a steel tube and a fire breaks out in the engine room, those 125 people onboard expect you to handle this confidently and correctly. You need to think through multiple scenarios simultaneously, to weigh different factors and arrive at the best solution. Your people expect you to have the right answer.
In any field, what I believe people want more than anything is transparency from their leaders. That’s why Spinnaker hosts quarterly All Hands meetings, where we offer a snapshot of our progress and look at emerging market conditions to discuss pivots in our strategy to pursue the right opportunities. Every member of this team has a responsibility in our company achieving its goals, whether short- or long-term. To do that, they need to understand the playing field and the role they play, because they benefit when the company succeeds. We also regularly celebrate our wins and the amazing milestones our team members reach.
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Shawn Sweeney: Teams reflect the attitudes of their leaders. If a leader is stressed and full of anxiety, your employees will pick up that negative energy. Similarly, if you’re upset and eager, those emotions are contagious. As leaders, you can’t expect to have a never-ending series of perfect days, but you need to be cautious of how you present that publicly.
By design, clients turn to us to help them navigate through very challenging situations, such as negative feedback from a regulator. Those situations typically generate a lot of stress within the client’s team, and a huge amount of work to get done in short order. Sometimes that workload and timeline can even be daunting to our team. But as a leader, you have to remain positive because that enables your team to stay focused on the task and move forward one step at a time. That positive attitude rubs off on the client’s teams, creating a more positive environment for everyone. If the client doesn’t remain positive and hopeful, the chances of success are low.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
Shawn Sweeney: During our 2020 SpinnakerFest — our annual meeting held hybrid in December — we shared a slide that spoke particularly to the past year: Calm seas never made a skilled sailor.
How can our readers further follow you online?
Shawn Sweeney: I’m on LinkedIn @Shawn Sweeney.
This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!
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