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Todd Alexander: “5 Things I Wish Someone Told Me Before I Became the CEO of Mattress Advisor”

Pruning” must happen every day. We know that sometimes you must “prune to grow” and that the “main thing is the main thing.” These simple mantras are easy to say, but I didn’t appreciate how relentlessly you must seek and find focus for the business. Much of my energy is spent curating, prioritizing, and pruning lists — and helping others do the same thing. There are so many things that can create drag in a business; rooting them out quickly is perhaps my most important job. The toughest call to make is pruning something that is profitable but lacks the explosive scale potential that the business demands. These things are blockers in the business. We decided to wind-up a Facebook program with several large brands and shift resources to our core organic search growth — something with a far less certain return, but also an order of magnitude bigger potential for growth. The small things matter too. Our weekly management team meeting includes the capture and prioritization of issues to solve, and the bottom quartile are often pruned from the list.

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Todd Alexander, Co-founder and CEO of Mattress Advisor.

Todd Alexander is co-founder and CEO of Mattress Advisor, a digital media and customer acquisition platform focused on sleep health and related products. He is also a Managing Director at Three Ships, a family of digital businesses that includes flagship websites MattressAdvisor.com, MattressNerd.com, RemedyReview.com, and HouseMethod.com. Prior to co-founding Mattress Advisor, Todd held several senior executive leadership positions in the digital media and customer acquisition industry, including Senior Vice President, Head of Life Insurance at TRANZACT and Executive Vice President at Red Ventures, where he managed over 500 technology, digital marketing and sales professionals responsible for acquiring millions of new customers each year for Fortune 100 brands.

Todd has led teams in other VC-backed startup and Fortune 30 environments. He was Head of Finance at V-Vehicle Company (later Next Autoworks), a new American car company backed by Kleiner Perkins Caufield & Byers and Google Ventures. He also led strategy and business development initiatives for The Boeing Company. Prior to enrolling at Harvard Business School, Todd began his career as a securities analyst and bond trader with a fast-growing relative value fixed income hedge fund.

Todd earned his MBA from Harvard Business School, where he graduated with Distinction, and Bachelor of Science in Business Administration with Highest Distinction from UNC Chapel Hill.

Thank you so much for joining us in this interview series! Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

When I co-founded Mattress Advisor and launched our flagship website in October 2017, my biggest challenge was quickly establishing credibility with the leading mattress brands. In a fast-moving market where the most valuable currency is consumer traffic, we had none.

To win the attention of brands, we decided to bet big on video to bring product reviews to life for consumers. We took a leap of faith and spent a quarter million dollars building a state-of-the-art video studio to film our mattress tests. We created a proprietary testing methodology with the help of respected mattress engineers and tested more than 50 top brands — all before we had any website traffic. The quality and professionalism of our content was an order of magnitude better than anything out there. One top-5 mattress CEO told us he could tell we played a different game and immediately brought his team to our headquarters for a day to learn about our business. The lesson: answer the consumer, and others will answer you. In our case, consumers expect high-quality, expert content, and the brands that pay us know it. And while it’s important to look for quick, capital-efficient wins, sometimes it takes big bets to raise the bar in a way that gets you noticed.

What are some of the factors that you believe led to your eventual success?

More than anything else, it has been persistence. Building a valuable business is a long journey with plenty of high highs and low lows. We try hard to avoid the rollercoaster and focus relentlessly on inputs. Persistence is trusting inputs and letting the outputs follow. For nearly six months, we debated abandoning our paid advertising efforts because we simply couldn’t make money. All the while, we used precious cash. Steady, compounding gains allowed us to ramp sales volume which in turn won deeper relationships with the top brands. Today it’s one of our biggest channels. Organic search never grows as fast as you want, and the growth is never linear. Perhaps nothing requires more persistence than organic search. At the individual level, you simply must gut it out. Jeff Bezos famously said you can work long, hard, or smart — “but at Amazon.com, you can’t choose two out of three.” I agree, for any growth business.

A few other factors stand out. Deep investment in relationships: Part of our edge has been spending the time and energy to learn our brand partners’ business and personal goals intimately. It matters to them, and in my experience, most return it in kind. Building real capability with the best talent: our business is powered by great people and digital capabilities that our competitors simply don’t match. Velocity and rigor: Speed alone is not enough — we pride ourselves on analyzing deeply and acting quickly, in equal measure. Luck: Oprah says luck is preparation meeting opportunity. I think it’s just luck, and you have to find some. We’ve had our fair share.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”?

1. The business will eat you, if you let it. I’ve always prided myself on a tougher-than-nails work ethic. When you are responsible for employees, consumers, investors, and of course the people at home who count on you to provide, you’re capable of pushing yourself to new and unsustainable limits. Especially when the work is fun and rewarding; sometimes you don’t want to stop! We all make sacrifices, but it took a real health scare to open my eyes to just how far I had pushed it. During the holiday season of 2018, I developed a prostate issue; I was only thirty-six years old. Hours at a desk, sitting on planes, trains, and in automobiles, caffeine, alcohol, and other bad habits had all taken their toll. Most alarming was the doctor’s sharpest warning — the pain and inflammation was tied to stress, and that this very condition had cost other patients their careers because they couldn’t reel it in. The immediate prescription included Epsom salt baths and less travel, but long-term recovery has required me to focus my time and intensity in a way that doesn’t overrun a healthy lifestyle.

2. Talent acquisition does not equal hiring. Nothing is more important than getting the right people on the bus, at the right time, and in the right seat. As a lean startup, we often let our capacity trail demand. The approach has allowed us to control overhead, but at important times, it has also left us behind when we needed new skills or more throughput. Anticipating the need and building a world-class, ready pipeline is how you beat the competition with talent. Hiring from a standing start is not fast. It can also force urgent decisions that miss on either competency, culture fit, or both. It took over six months to fill a critical paid media leadership role, in large part because I started the search after realizing and defining the need. At first blush, that sounds perfectly reasonable; however, talent acquisition isn’t the same thing as hiring. Talent acquisition is always on. It’s proactively building a pipeline of high-performing, high-potential people who share your values and can create business value, when the time is right. Today we have standing job postings for capability areas we know can help us scale faster and win long-term. I interview at least one person every week — usually for potential instead of a specific job to fill.

3. Influential communication is everything, and it takes so much practice. I consider myself a reasonably seasoned communicator, but nothing prepared me for the volume and velocity of communication that’s required to build a team from scratch and breakthrough to scale on a startup business. It may be your board, the CEO of a key partner, a direct report, or the accounts payable manager in a customer’s back office — the audience changes quickly, but the standard never does. Every communication must be purposeful and impactful. After closing a growth financing round and adding two managers, our first board meeting was terrible. I hadn’t taken the time to understand their interest areas or thoughtfully consider how they could help. I’ve been caught flat-footed by a tough question from a customer. I’ve delivered unconstructive feedback to a young, inexperienced team member. These moments and many more were missed opportunities. I still make mistakes, but I work harder than ever to prepare for important messages.

4. Business velocity is all about YOU. It’s easy to get frustrated when things don’t happen as fast as you would like. The tone and model you set, the operating battle rhythm you design, and the culture you nurture all determine the direction and speed your organization achieves. Sometimes you are very plainly on the critical path. It may be an important decision. It may be day-to-day operations. In July 2019, down a resource and awaiting the start of our new head of paid media, I ran our search advertising accounts. That month we only went as fast as I worked. More often though, it’s the track you’ve laid as a leader that determines how fast the team’s wheels will turn. I try hard to stay out of the way. We have a culture of “judgement, not rules.” It guides behaviors and challenges team members to always do what’s best for the business. We have operating plans that offer waypoints, but also a general management ethic that values adaptability and agility. Still, my presence is felt in every decision or action, many of which I don’t even know exist. When members of my team act tentatively, often it’s a lack of certainty in me, not themselves. I’m having to find new leadership gears of my own to help the team go as fast as we need to win.

5. “Pruning” must happen every day. We know that sometimes you must “prune to grow” and that the “main thing is the main thing.” These simple mantras are easy to say, but I didn’t appreciate how relentlessly you must seek and find focus for the business. Much of my energy is spent curating, prioritizing, and pruning lists — and helping others do the same thing. There are so many things that can create drag in a business; rooting them out quickly is perhaps my most important job. The toughest call to make is pruning something that is profitable but lacks the explosive scale potential that the business demands. These things are blockers in the business. We decided to wind-up a Facebook program with several large brands and shift resources to our core organic search growth — something with a far less certain return, but also an order of magnitude bigger potential for growth. The small things matter too. Our weekly management team meeting includes the capture and prioritization of issues to solve, and the bottom quartile are often pruned from the list.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

I often tell job candidates that a role must do at least two of three things for the person in it to stay energized: use your strengths, access your passions, and deliver sought-after learning. With all three, you’re an unstoppable force. You’re in the zone. With only one, you’re in trouble. In the long-run, I firmly believe happy, energized people use their strengths every day. It feels good to perform and accomplish what you’re uniquely good at; it’s a battery that’s always recharging. Organizationally, I find that mid-term goals are a powerful way to maintain poise and energy, especially when they’re captured in compelling narratives that the team can remember and revisit when they need. Short-term goals are useful but can also feel frantic and unmoored. Long-term goals are necessary but can also grow distant and abstract. Smart mid-term goals met can deliver a “runner’s high” in business.

There are many more ways to recharge, but a few to call out. The people, places, and rituals you keep outside of your work: family, friends, faith, exercise, hobbies, charity, travel…we must maintain reasonable margin in our lives for the other things that fill us up. External stimuli: books, magazines, coffee chats, conferences…I encourage our team to regularly leave our walls, physical and virtual, to find new sources of inspiration. Small, compounding changes: It may be as simple as updating the seating chart in your office. We must literally create fresh perspectives.

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?

The business and my career would not be where they are today without my Harvard Business School classmate and co-founder Zach Clayton. Zach is one of the most intellectually curious and hyper-focused leaders I’ve ever met. He’s unequivocally the hardest working person I know. His experience and track record as a serial entrepreneur have been a strong tailwind for the business. More, his counsel and the fellowship we’ve developed as friends and business partners have grown my confidence — to make decisions and execute for the business, but also to ask for help when I’m unsure or stuck. The business is stronger, and I’m a better thinker, operator and leader, because of Zach.

He and his family are also kind, big-hearted people. I live in Charlotte, and our team is headquartered in Raleigh, NC. Every Monday I commute by train to Raleigh, returning to Charlotte Tuesday evening. Zach and his family graciously let me use a spare bedroom in their home whenever I’m in Raleigh. Since the fourth quarter of 2017, I’ve stayed at Zach’s house most Monday nights. Allowing me to share that space and time with his family is an incredible gift. As often as we can, we exercise together on Tuesday mornings. Over many four-mile runs, we’ve settled debates, made business calls, defused tension, and become closer friends.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

I do a good job setting and following-through on quarterly and annual goals for the business and my role in it. Hitting those targets creates momentum, unlocks growth, and allows tremendous optionality. That’s gratifying to me. We discuss three, five, or even ten-year goals, but I think those exercises are best at aligning the team on a mission and vision for the business and nurturing a winning spirit. It may sound near-sighted, but I keep my own professional vision reasonably short, too. In sports terms, if I can win seventeen straight games like the 1972 Dolphins, then the Super Bowl will come. As a business leader, I aspire for our alumni — the people who leave our team — to remember their experience as a time of high-impact growth and development. I hope they remember me as honest, fair, and supportive.

Balancing — better, integrating — my work and personal lives is my biggest focus area and most nagging challenge. Too often I compartmentalize my professional and personal lives, and if one of those compartments is prone to overgrow and crowd-out, then it’s the professional one. I do try to slow down and set more specific personal goals; most often they’re resolutions each New Year. A few are worth sharing: Read a book a week. Run a thousand miles in a year. Join a life group at my church. Take at least two vacations a year, one with the entire family and one with just my wife. Write a book. Teach a college class. Support at least one social cause in my city through both giving and advisory.

What do you hope to leave as your lasting legacy?

I certainly want to build a business that has longevity and meaning for other people — a business that creates and sustains rewarding jobs, helps consumers and evolves with their needs, and earns a strong return for shareholders. I also hope the business can do good and well at the same time. In December 2019 we’re kicking-off our “Dream Team” social impact initiative targeting child bed poverty. We’re donating 100 brand new twin mattresses to Beds for Kids, a Charlotte, NC based organization that distributes bedding and related furniture to families in need. The donation will take a 10% bite out of Beds for Kids’ “Thousand Bed Challenge,” a Giving Tuesday drive to raise funds and collect mattresses for 2020. A clean, comfortable place to sleep can have a dramatic impact on a child’s behavior, learning and long-term cognitive development. We’re privileged to do our small part to help.

More than anything, I hope my lasting legacy is the far greater impact my two sons have on the world — that the accumulation of my work, experiences, relationships, and the passing along of it all have a multiplying effect on their lives and the lives they touch. I hope they trust me enough to stand on my shoulders and then grow ten times as tall. I hope my lasting legacy is as a great dad.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

I would focus on voter registration and turn-out. The key to a more perfect version of our democracy is participation. The true heart of America is tough to judge in the words and work of our elected officials when only 55% to 60% of the voting-eligible population votes in presidential elections. The future is fully ours to shape, but only if we show up.

How can our readers follow you on social media?

My social media footprint is purposefully small. The best way to follow or reach me is LinkedIn; I try to be as responsive as possible. I enjoy Instagram and believe the platform adds unique value, but my account is private. I keep it for my family and friends. I have a Facebook account but haven’t touched my profile in years. I’ve wavered a bit on the platform and its usefulness in my life. In my opinion, the user experience and quality of content have degraded over time; for one reason or another, it doesn’t seem to stir to the surface the best of who we are. I’m considering deleting my account. I have a Twitter account, but I’ve never written anything; maybe I’ll change one day, but a big audience has never been intrinsically rewarding to me.

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Carly Martinetti

Carly Martinetti

2x pet tech founder, publicist, writer, and dog mom. I love learning about what makes CEOs tick.