Tory Schalkle

Tory Schalkle is a Senior Vice President of Strategy at U.S. Bank, where he brings over a decade of experience in topics like new market entry, acquisition and growth, segmentation, customer depth and loyalty programs, etc. Prior to U.S. Bank, he was a management consultant, ran a $300 million business, and worked on another Fortune 100 strategy team. He’s based out of Wayzata, MN, where he’s involved in state and local charities like advisory committees for his town’s city council, a governor-appointed workforce development board, and a $30 million public-private partnership aimed at developing his town’s lakefront downtown district. His first non-profit venture was recognized by President Obama as a “Champion of Change”.

Recently, Tory Schalkle and his wife started Firm Footing – a non-profit aimed at providing recently reentered and rehabilitated populations gain financial independence through knowledge, skills-training, and follow-up coaching. It currently partners with a non-profit in North Minneapolis to work with recently reentered participants.

Where did the idea for your career come from?

Working in Financial Services, I was well aware of the statistics around how much of the U.S. population is unbanked or underbanked, and the underlying, qualitative sentiments driving those numbers. As part of that, I saw how often our financial system wasn’t set up to work well for many people, often causing generational disfunction. But was what really spurred me to action was clearly seeing how there was little incentive for organizations to help them. When I dug deeper and looked at who was most underserved, it was clear that it was those with a criminal conviction.

Half of Americans have had a “close family member” in jail. There are 83% odds that a person will be back there unless something happens. 93% of the reason they’ll be back there (i.e. the primary motivator behind most crimes of recidivism) is financial needs. But the financial system isn’t set up for this population. That’s why they’re 2-4x more likely to use payday loans, etc. that further desperation. So the treadmill pulls them back in – those who committed crimes out of desperation don’t have a way or knowledge to get out of that cycle. So preventing a former convict from getting into financial desperation is a crime prevented and a life rebuilt/reclaimed. And the data supports this – 75% of inmates with bank accounts do NOT return to prison, while only 39% of those who return have bank accounts.

The problem is, there is no financial literacy program for this population. Doing that would require collaboration between bankers, banking regulators, and prisons, using each of their perspectives and superpowers. So that’s what we did! I partnered with a Department of Banking and Securities to create a curriculum while also partnering with recently incarcerated to understand their specific frustrations, tips, tools, etc. for navigating the financial system as it is. The result is a combination of training and individualized coaching to help rehabilitated reenters make a new life and overcome financial struggles – declaring bankruptcy, rebuilding their credit, making a budget, opening savings, etc. As for the results of financial literacy courses? In some ways, it’s too soon to say, but a RAND (the nonpartisan non-profit/ think tank) report found that inmates who received them have 43% lower odds of winding up back in prison than those who don’t.

We’re still in the start-up phase, but we’d love to expand it into something that could hire reentered individuals to be individual coaches with participants.

What does your typical day look like and how do you make it productive?

Well, the work for Firm Footing is all done on weekends and Monday nights. Weekend work might look like logging on when kids are asleep and researching a participant’s pressing question, continuing to build out the curriculum, etc. What makes it most productive is carving out time for it – since it’s not a day job, preserving dedicated time to it as sacred space ensures the work gets done.

How do you bring ideas to life?

Coming up with ideas is something I enjoy and a strength. But bringing them to life is tough because I have a temptation to overthink and/or want to work on something until it’s perfect, which it never will be. So, for me, bringing ideas to life has required two things. The first is making SMART goals – saying what I want to do with that idea, by when, and how I’ll get it done. The second, and it’s a subset of the first, is defining a “good enough” point – where I realize it’s not great, but it will work, and that’s good enough for the output I need to move forward.

What’s one trend that excites you?

Workforce Analytics – i.e. quantifying work and workers more (think Moneyball for the workplace). There are a few ways this could go dystopian, such as the current workplace culture at Amazon warehouses, but there are also ways this could be exciting. We spend ⅓ of our day at work, and most Americans say it’s in jobs they hate. And companies’ #1 expense is in labor, often not fully utilized. So it’s hugely important to both employer and employee, yet current matching mechanisms (e.g., hiring and promoting decisions) are often so subjective and wrought with bias. So workforce analytics better allows us to say “what does make someone successful in this role, and how can we better spot them”, “who is most likely to leave, and how can we better retain them”? And better answers to those questions will make workers’ lives more meaningful and employers’ labor costs more productive.

What is one habit of yours that makes you more productive as an entrepreneur?

Timeboxing. I may just speak for myself (but a recent HBR article testing various time management methods bore this out too), but To-Do lists stay wishlists unless they’re tied to a date/time. Timeboxing is taking the task you want to be done and slotting it into your calendar. What I love about this is (1) you can understand when you’re truly too busy, and when that task is likely to get done, (2) it forces you to prioritize – as my dad says “it’s not that you didn’t have time; it’s that you didn’t make it a priority”, (3) it provides parameters around it. I love that there’s an end time to it – even if I estimate it. That helps me feel more comfortable wrapping it up and moving on.

What advice would you give your younger self?

Sleep more. “Every minute you’re awake is slow-motion mental erosion,” as one sleep author has said. Sleep is not quitting today; sleep is preparing for tomorrow.

Tell us something that’s true that almost nobody agrees with you on.

I love this question. I think it’s that employers should, even informally as a norm, not ask/ disregard educational institutions. I’m baffled by how much weight hiring managers to give to the college that someone picked when they were 17 as a sign of how qualified they are now at 37. The thinking is often “well if they were smart enough to be accepted there, they must be smart”. But there are obviously so many reasons someone could have gotten into a college (e.g., athletic scholarship, legacy status), or why they declined certain colleges (e.g., financial hardship, cultural fit). Beyond that, there are so many nuances to a job that the institution you read textbooks in seems like a poor indicator. A better proposal is two-fold: (1) leverage Workforce Analytics to better understand what factors you need in this open role and what could indicate whether this candidate has it and (2) ignore or don’t ask about where they did their studies. If they’re smart, and if that institution was so amazing, it should show in a phenomenal interview and work expertise.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Continually trying to drop any ego. That means seeking out someone who thinks your idea is bad, and not taking anything personally. It means getting uncomfortable if everyone is agreeing with you or not pushing back. It involves admitting I’m wrong a lot or saying I’m sorry a lot. It means realizing I’d probably make the same choice another person made if I was in their shoes.

What is one strategy that has helped you grow your business?

“Growing” is less relevant in our context as a non-profit, but it has been a key question we continue to wrestle with – do we focus on at-scale, base-level education (e.g., the same curriculum given to everyone), or do we work on individualized, labor-intensive coaching (e.g., one-on-one weekly sessions going over a person’s specific issues). The answer is whatever drives the most impact, and we’re still assessing what that is, or whether it’s some type of hybrid.

What is one failure you had as an entrepreneur, and how did you overcome it?

We have so many failures ahead of us, for sure. But thus far the biggest one is waiting. I wish we had just started sooner – small and imperfect but tried. Just to test the waters and see if something is there.

What is one business idea that you’re willing to give away to our readers?

A lot of short-haul and long-haul trucks and containers are driving on the road empty as they return from their destination. Since consolidation in that part of the transportation industry isn’t possible, some type of integrated matchmaking (e.g., an Uber for long haul trucks) would be needed to solve that.

What is the best $100 you recently spent? What and why?

I stopped being such a tightwad and paid to have our driveway plowed (we live in MN). On a morning when it’s just snowed 6 inches, it’s nice to just start the car and not have to get up early, get sore and sweaty shoveling, and come in freezing. I should have done it a long time ago.

What is one piece of software or a web service that helps you be productive?

I have not found a silver bullet software or service. In fact, I’ve found going back to the basics – using software only for its core use cases, minimizing apps, keeping it simple – has worked best for me so I don’t overcomplicate things. Right now, my core software tool is a Google Spreadsheet that’s the one-stop-shop for deliverables, owners, and timing – so everyone knows what needs to be done, by whom, and when. It’s not sexy but it gives clarity, which leads to action… and what’s better than that?

What is the one book that you recommend our community should read and why?

“The Color of Money”. Our current Financial System didn’t pop up in a vacuum, and other financial systems look very different. Understanding our current wealth landscape – and the startling racial imbalances within it – means understanding the context in which it was built, the inherent components our system has, and thus the impact it’s had on different communities was helpful to understand how we arrived at our current (very unideal) state.

What is your favorite quote?

“Do onto others as you would have them do unto you.” First, a core conviction of mine is that we are all inherently equal and valuable. But beyond some platitudes like “Be kind” or “Do well by doing good”, I like the litmus test and gut-check it provides – “What if I was on the receiving end of my action?”

Key Learnings:

• Having a growth mindset – there is so much information available online, once you pick what you want to learn, finding the best educational tools to help you get there is key. But having that intellectual curiosity to continue to learn has paid dividends for both my personal and professional growth.
• Enjoy the now – It is very easy as an entrepreneur to be thinking 5-10 years out about your strategy, business plans, etc. But if you’re not enjoying it ‘in the now”, is it all worth it? I really enjoy all that I am doing and I love sharing these strategies with other business owners.
• Do not be afraid to fail. Every great entrepreneur learns from their mistakes and comes back even better having learned from the pain.
• Find a mentor to gain a new perspective.
• Learn that neither rejection nor failure is the end of the world.