Two kinds of “what if”

About

Hi, I’m Ben. You’ve found my little corner of the internet — where I read and write about marketing, product, leadership, learning, books, fatherhood, and anything else that happens to inspire me on a given Thursday.

In my work life, I love sitting at the intersection of go-to-market and product: everything from the first pixel in Figma to the story and messaging we carry into the market. But at the end of the day, I follow the great University of Michigan mantra, “the team, the team, the team.” I love building a team, working hard together to accomplish something special, and helping the humans around me do better work and live better lives.

Outside the office, I’m a dad to four stellar kids, a relentless reader (see some of my faves and find your next book rec here), and an adopted Hoosier. Most days you’ll find me walking the streets of Indy with my fam, rewatching The West Wing for the hundredth time, or attempting to win Star Baker. Always happy to connect or help however I can.

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Experience

VP, Product Marketing Docebo 2025–Present

I serve the product marketing, competitive intelligence, customer marketing, and customer education teams at Docebo, a global learning platform.
SVP, Product & Marketing Your Money Line 2022–2025
I joined this post-Series A financial wellness startup as VP of Marketing in late 2022, and two years later stepped up to SVP, Product & Marketing — leading marketing, product, and engineering.
Other roles
- VP of Marketing
Founder Hoosiers Read 2019–2023

I founded a nonprofit with a simple mission: bring books to every child in Indiana ages 0–5, in partnership with Dolly Parton’s Imagination Library. After a $1M beta across five counties, we successfully lobbied the state to take the program statewide with $6M in funding.
Senior Director, Brand & Creative Seismic 2021–2022

I led the brand, design, video, PR, copy, and social teams at Seismic. Two favorite moments: the 2022 global rebrand — new brand strategy, logo, visual identity, voice and tone, and website — and launching the Seismic Enablement Cloud with activation across PR, social, web, and even Times Square.
Chief of Staff Lessonly 2017–2022
Four roles over five years at Indianapolis’ beloved training-software startup. I started as Content Marketing Lead, then as Marketing Manager partnered with CEO Max Yoder to edit, produce, and launch his book Do Better Work. As Director of Marketing I led inbound marketing and sales development — demand gen (owning a revenue number), content, SEO, product marketing, marketing operations, email, paid, social, PR, and web.

I returned as Chief of Staff, working closely with the CEO and President on the rhythm of the business: company objectives, pricing & packaging, weekly all-hands, and our biannual all-company gatherings. After we were acquired, I led the Lessonly side of the integration with Seismic.
Other roles
- Director of Marketing
- Marketing Manager, Communications & Content
- Content Marketing Lead
VP of Marketing Pillar 2020–2021

An early exec-team member at Luma (now Pillar), a High Alpha studio company on a mission to make job interviews more equitable and effective through ML/AI. When the founders moved on, I briefly led the business until a new CEO was hired.
Leadership Fellow Mitch Daniels Leadership Foundation 2019–2020

A yearlong fellowship that gathers a small cohort of Indiana leaders to study and practice civic leadership, in the spirit of Governor Mitch Daniels.
MBA, Operations & Corporate Strategy University of Michigan — Ross School of Business 2017–2019

Earned my MBA with High Distinction (summa cum laude), and had the honor of speaking at the 2019 Ross commencement — a speech called “It Depends,” an idea that later became a post here in the blog.
Area Director II Young Life 2012–2017
Five years on staff with the youth ministry nonprofit, growing from Staff Associate to Area Director II — leading volunteer teams, fundraising, and programs for teenagers.
Other roles
- Area Director I
- Staff Associate
BA, Political Science & International Studies Northwestern University 2009–2012

Studied political science and international studies, alongside integrated marketing & communications.

All posts

Writing

The abnormally unselfish basketball playerJuly 21, 2026It's great to work with stars, hit the personal or team metrics, and get celebrated. But as for me, I want to show up at work more like Shane Battier.
Three minutes with José AndrésApril 24, 2026The value of friendship and kindness. A posture of gratitude and vulnerability. Leaders who bring out our best angels.
The human experience is the extraordinary partApril 13, 2026Science, competence, achievement—Artemis II showed it. But what made it special was something more human.
Great managers protect joyMarch 31, 2026One recurring signal of a great manager I’ve seen play out again and again: their people feel joy at work. And joy isn’t just a perk—it’s a performance engine.
The bottleneck isn’t creation anymoreMarch 23, 2026The oncoming issue with AI isn’t about how much it can do. It’s about how much humans can verify.
Plumbing and poetryOctober 24, 2025Plumbing is about effectiveness. Poetry is about meaning. Great leaders do both.
What brand love looks likeSeptember 17, 2025The true ROI of brand building? When your customers—even 10-year-olds—show up excited and proud to be part of your story.
Strengths and shadowsAugust 27, 2025Every leader has strengths and shadows, on a continuum that ebbs and flows. A framework that changed how I connect with the people I work with.
On tasteJune 5, 2025Sarah Guo’s essay on taste is one of my favorite business reads in a while. Taste begins as loneliness and ends as leadership.
Some spring readingApril 25, 2025A handful of fiction and nonfiction favorites lately—and I’m building my summer list now.
Pope Francis’ 15 diseases of leadershipApril 23, 2025A list from a 2014 homily that hit home: fifteen ways leaders quietly lose their way.
A Duolingo streak and a product principles handbookFebruary 12, 2025My 9-year-old’s Duolingo streak got our whole family learning—and Duolingo’s public product principles are a gold mine for builders.
Why Stripe’s operating principles workOctober 28, 2024Not vanilla “integrity” and “teamwork.” A case study in operating principles that are specific, unique, and actually inform behavior.
The 11 paradoxes of leadershipApril 29, 2024Leaders live in tension. Lego trains its managers on eleven of them—and I think about them constantly.
Accountability and empathy aren’t oppositesApril 8, 2024Every manager I know has struggled with the tension between accountability and empathy. The trap is thinking you have to choose.
The Heart of BusinessJune 12, 2022This was a refreshing and encouraging read from a big company CEO, advocating for a more purposeful & noble role for work.
14 lessons from sunsetting a marketing siteApril 7, 2022We took down the Lessonly.com marketing site after five years. Here's what building and rebuilding it taught me about brand, demand, and copy.
10 things I read, watched, and listened to in 2020January 30, 2021At the start of every year, I reflect on the content I’ve consumed that’s had the greatest impact on me.
Clear your calendarNovember 20, 2020Sometimes our biggest problems feel insurmountable.
Dear first time manager…November 20, 2020Or, 7 ways to be a new kind of leader
The X factor of great teammatesNovember 10, 2020I’m becoming convinced that there’s a X factor in being a great teammate or becoming a better leader.
Spine PoetryOctober 29, 2020Last night my wife introduced me to spine poetry, and I am captivated. Here’s my first go at it!
Marketing savantsAugust 20, 2020Marketers —I am not a savant, and I bet you aren’t either.
Two kinds of “what if”August 1, 2020We all have imperfect information about the future.
4 books to think bigger and think differentJuly 23, 2020Two kinds of books I love:
“It Depends” LeadershipMay 12, 2020Two years ago, I sat down to tackle my first business school case. It was about a popcorn company.
The More Perfect LeaderApril 28, 2020I was recently chatting with a small group of fellow managers about the biggest challenge on our minds right now—how should we lead our teams while working remote during a…
What I read and learned in 2019February 25, 2020A friend of mine recently asked me what books, shows, people, practices, or ideas shaped my 2019. Here’s what I said back…
Leadership is GardeningFebruary 24, 2020Our schema for leaders is heroes. They’re cape-wearers and chessmasters who command and wield power, winning by being smarter, better, faster, stronger (all the “-ers”).
Call Sign Chaos: leadership takeawaysJanuary 10, 2020One of the best leadership books I’ve read in a while. A few of Mattis’s lines on coaching, trust, and reading widely that stuck with me.
The Heartbeat of Great TeamsMarch 23, 2019My life is a conglomeration of teams. During every day at Lessonly, every project at Michigan Ross, and every moment in-between with my family, I’m part of a team.
Why nonprofit leaders need agileJuly 7, 2018Since graduating from college, I have worked at two companies. The first was one of the largest nonprofits in the world. The second is a thriving SaaS startup.
Give Away the KeysDecember 12, 2017A few years ago, my friend Jack and I sat down to lunch with an experienced restaurateur.
Are you a sponge or mirror?October 20, 2017Two phenomena of leadership are at play when a team succeeds — the sponge, and the mirror.

Two kinds of “what if”

August 1, 2020

We all have imperfect information about the future.

Uncertainty is an undeniable companion in life and work. Do people like me? Is this the right job for me? Will I hit that goal? Will [fill-in-the-blank situation or relationship] work out like I want it to?

We often fill in the gaping hole of certainty with “what-if” scenarios. I’ve encountered two primary kinds of “what if”:

The limiting “what-if” hijacks our fear to keep us thinking small. These worst-case scenarios include the greatest hits, “What if this goes wrong? What if I’m seen as a failure? What if no one like me?” While these may serve as fodder for personal change, more often than not they cause us to retreat from creativity confidence, contrarian thought, and meaningful work.

The expansive “what-if” asks what’s possible and then gets 3 sizes bigger. It poses, “What if we tried…” “What if we wanted to reach 10x our goal?” “What if we reframed this situation?” “What if this were radically successful?” The expansive “what-if” sees opportunity instead of threat—it causes us to lean in rather than play defense. **We become more creative, more bold, more thoughtful.

Think about that big project or idea in your life. What if you chose a new “what-if”?

All books

Library

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