Tobi Walter - COO and Co-Founder of

[quote style=”boxed”]Analyze (data is your friend 😉 ) and over-communicate (I’m a big believer in the hypothesis that startups work so well because everybody constantly knows what’s going on, why things work and why they don’t).[/quote]

Tobi Walter is the COO and Co-Founder of, the preferred small business expense tracking solution for over 500,000 users worldwide; fighting the seemingly unnecessary bookkeeping hassles for Small Business Superheros around the globe.

An investment banker turned entrepreneur, Tobi got his MBA from top business schools in Germany and France before working with Societe Generale in Capital Markets and Morgan Stanley in Mergers and Acquisitions.

In 2006, Tobi joined his first start-up – studiVZ (think: the German Facebook) – during its founding days and became part of the six person management team of the later 200 employee company. As the company’s VP of International Markets, Tobi led the site’s roll-out to eight foreign markets, leading a team of 60 people. He was also intimately involved in the acquisition of studiVZ for €85 million in 2007, before starting Shoeboxed in 2008.

What are you working on right now?

We are currently working on adding quite a few new products to Specifically, we are building our service out to be a real virtual bookkeeper that helps people reconcile accounts, get reimbursed faster, and know what expenses they are missing.

Oh, I’m also trying to gain 15 pounds as part of an office bet.

Where did the idea for come from?

After the last startup that my co-founder Taylor Mingos and I worked for was acquired, we started brainstorming the next problem we wanted to solve. One thing that didn’t make sense to us was the time that people spend keeping up with paper receipts, bills, and invoices. It seemed stupid that in the 21st century we still get little pieces of paper dozens of times a week that we have to keep up with. The information on them is important, but they are such a pain to deal with.

We wanted to make it easy for businesses and individuals to keep an archive of all of them, have an online overview of what they bought, where they shopped and take the hassle out of dealing with records for bookkeeping, tax deductions, reimbursements and so much more.

How do you make money?

Shoeboxed is a subscription service that starts at $9.95 per month to have a premium Shoeboxed account where users can hand off all their receipts to us. We extract and categorize the data, export it into the accounting tools they use and send reimbursement and receipt requests for them.

What does your typical day look like?

I do multiple math quizzes on my alarm app to get myself out of bed; start with a lot of coffee; do the daily morning Shoeboxed cheer (just kidding); and then try to stick to my rule of “No administrative work before6pm.” Most of my day involves talking with customers, the team, partners and investors as well as carrying out marketing and product brainstorming sessions before getting back to my desk to answer the mound of emails. Inevitably, some nights end with me crashing on a couch in the office.

How do you bring ideas to life?

Very “Lean Startup-y”: we keep a running list of ideas from our team, customers and partners and every few weeks we rank and prioritize them. We usually put out a quick experiment (can be as easy as an email pitching a [not-yet-built] product to some of our customers) to figure out which ideas are popular before we invest time in them.

What’s one trend that really excites you?

Has anybody here said ‘mobile’ yet? The idea that your phone knows absolutely everything about you- whether you’re asleep or awake, where you live, where you work, what you have to do today, what your friends are doing right now – still absolutely amazes me and I genuinely believe we haven’t even started exploring 10% of what we could do with that.

What was the worst job you ever had and what did you learn from it?

I sold ice cream and beer in German soccer stadiums during high school. The idea sounded great – making money to watch soccer games and walking around with a beer backpack. In reality though, I didn’t really make any money if you factored in the time it took me to get there and how much earlier I had to get there to clean up. Also, I didn’t really see the games because I was constantly running around trying to solve problem #1 (how to make more money). Quite honestly, the job sucked. The lesson? – Do what you are really passionate about; every single day, every single second – don’t do something because one or two perks sound great (they might never come true).

If you were to start again, what would you do differently?

Be really good at “hire slow, fire fast”. I would make sure that right from the start I would have a team comprised only of full-time people who are fully dedicated (instead of dozens of interns to keep the company lean). Ideally I would give myself a lot more time to actually test potential employees, even if it was working together at night or on the weekends, to make sure they have what it takes to become a good member of the team.

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

Analyze (data is your friend 😉 ) and over-communicate (I’m a big believer in the hypothesis that startups work so well because everybody constantly knows what’s going on, why things work and why they don’t).

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

We failed in 2009 raising our first institutional financing round (yes, bad timing, but I think we have also learned a lot from it in regard to fundraising and our actual business). We had to re-focus on building an actual, profitable business fast. Instead of doing a big VC round, we raised a few hundred thousand in angel funding and were able to become profitable within a year and a half.

In retrospect it was very helpful for building our business in a scrappy fashion, becoming close to our customers and narrowing our focus. After becoming profitable in 2011 we raised our first institutional round with Novak Biddle Venture Partners (a really amazing partner and great investor for anybody out there looking to raise money!).

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

I still don’t understand why a personal assistant is somebody I need to actually talk to and pay hundreds of dollars a month for. I would love to have an app that handles the simple recurring things so I don’t have to.

An app should know that I need new deodorant every three weeks and it should order it for me, it should schedule my laundry pick up and remind me the morning of pick up via push notification to put it out; it should schedule my haircuts when it sees I have a free hour on my schedule and it should get somebody to clean my car when it knows I will be at the office and don’t need to drive it. I have a bunch more of these – just ask me 😉

If you could change one thing in the world, what would it be and how would you go about it?

No more war (if anybody has any idea how to do that – please let me know!).

Tell us something about you that very few people know?

I ran for city council when I was 18 and failed miserably.

What are your three favorite online tools or resources and what do you love about them? (love them for invoicing), Evernote (I keep all my notes there), and KissMetrics (great analytics).

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

This might get old, but it is really the one book everybody should read: The Lean Startup – Eric Ries.

When was the last time you laughed out loud? What caused it?

Last Friday (we do beers with the team every Friday afternoon), when one of our designers said, “Tobi’s last words are going to be: ‘Here, hold my beer.’”

Who is your hero, and why?

Professionally – still Richard Branson (Elon Musk is becoming a close second).
Personally – My father. Losing him about two years ago was the hardest thing I have ever had to go through. Spend time with your families! Please! Despite the hundred hour weeks that you’re pulling, spending time with your family is always worth it.

What is the most important piece of advice you would give aspiring entrepreneurs?

Never start a company alone! You have no idea how many hardships you will go through and you need a partner. Plus, you need a counterpart: if you are the visionary, you need an executor; if you are the salesperson, you need somebody to figure out how to deliver what you overpromised; if you are the perfectionist, you need somebody who will tell you to just go out right now and sell it; if you are a genuinely nice, loving and caring person, you need a hard-ass (or at least somebody who can play it. And if you are the later one, you will definitely need the first one).

And when you do choose a co-founder, make sure you know that this is like entering into a marriage. Know the person inside and out and think hard about it – twice. Look at things like Important Questions Startup Co-Founders Should Ask Each Other but also ask things like ‘when do we give up?’, ‘how many hours a week will we work?’, ‘do we want to grow fast or slowly?’, etc. etc.

You said you like to travel. What is the best trip you ever took?

Right after graduating from business school, nine friends of mine and me decided to raise money to buy 5 used ambulances and drive them from Germany to a hospital that had just opened in Afghanistan. Out came a 4,000 mile road trip and an unbelievable 3-week experience that was completely off the beaten path. It was simply amazing seeing the Middle East from that perspective and getting to meet such unforgettable people.

Tobi Walter on LinkedIn: