All Posts in Bootstrapped

October 13, 2016 - No Comments!

How I launched my company without outside funding, connections, or even a track record, and how you can too.

Coming up:

As unknown undergrads with no prior network or track record, we would have to raise $1,000 a day, from total strangers, for 35 days straight.

This is where I honestly expected the story to end.

Somehow, it was just the beginning.

In this article, I’m going to share with you my own entrepreneurial journey. Are you embarking on yours, but stuck on something? If so, let’s schedule a time to chat. I’d love to see if I can share anything with you that might help. Just shoot me an email to schedule 30 minutes to discuss what you’re working on.


 

I’m lucky enough to run a young, bootstrapped company that I founded. Here’s how that came to be.

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In 2011, during my senior year at Virginia Tech, I was taking my favorite course — Design of Information. We had a journal check a few weeks into the semester, so the day before, I did what any college senior would do: I ran to Staples and bought a notebook.

To try and fill the minimum number of pages, I considered what problem would be so difficult that I wouldn’t be able to come to a fast solution on; one that would easily fill 10 pages.

I chose email. Everyone hated email, everyone complained about it, and it seemed that no one had figured out a good system for it (or if they had, it was intensely cumbersome).

I started to journal around email. I was trying to find the mismatch between how we actually use email today versus how it’s designed to work. My first challenge was to boil email down to its essence. I wanted to find the root of it: what the essence of email is to us today.

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Once I felt that I had figured that out, I ignored all previous ideas and implementations I had ever seen, and I designed how an email client would work, based solely around that essence.

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What I drew I quickly fell in love with.

I immediately showed it to my now-wife, and she resonated with the ideas immediately. The next day I showed it to a few friends, and their emphatic responses were clearly more than the minimum courtesy typically extended to a friend showing off scribbles in a notebook.

For a few weeks, I discussed the ideas with as many people as I could, refining them as I learned more, and iterating on the language I used to describe the concept. I kept hearing two things:

  1. “I need this,” and
  2. “I will pay money for this.”

That’s how I knew it was time to give it a shot.

With graduation 6 months away, I wanted to see if I could secure the funding to go full-time on the idea after college. But before turning to angel investors and VCs — a long shot, given that we had no experience, no connections, no prototype, and were still students — I wanted to first see if I could make an even longer shot work: crowdfunding.

The benefits of turning to a site like Kickstarter were that I would retain equity at this stage, and I wouldn’t be on the hook with someone else’s money if the idea failed (if it didn’t resonate in the market, then it wouldn’t be funded; conversely if it did resontate in the market, it would be funded, and a fan base would come with it — all three benefits tip together when a campaign reaches 100%, a feature unique to funding via the crowd with an all-or-nothing campaign).

We spent weeks prepping — recording a video, planning the kickbacks, very unsuccessfully reaching out to press and bloggers, writing content to publish during the campaign, starting to build up an email newsletter, etc.

In January of my senior year, with 5 months until graduation, we launched the Kickstarter campaign. We set the goal at $35,000 and the time at 5 weeks. As unknown undergrads with no prior network or track record, we’d have to raise $1,000 a day, from total strangers, for 35 days straight.

This is where I honestly expected the story to end.

Somehow, it was just the beginning.

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It blew up on Hacker News with the headline “Email is broken. But we fixed it.” (which was changed midway through the day), and Twitter shortly thereafter.

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People were backing the campaign faster than we expected, but we still feared it tapering off. The WIRED Insider selection was exciting nonetheless. Oh, and Jason Fried tweeting me about it didn’t hurt, either. (As a huge fan of his book REWORK, I geeked out when that tweet came in.)

A week into the campaign, David Pogue sent us a late Christmas gift:

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Pogue wrote an article about Kickstarter, focusing in on just a few campaigns. One was ours.

He called our idea for Mail Pilot “ingenious.” In the New York Times. In print. At this moment, amid all the excitement, I fully accepted that this was it; I had peaked in life, and this was as good as it gets. It was all downhill from here.

Luckily, I was wrong.

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After 5 weeks, our campaign ended with 1,623 backers pledging $54,205 to make Mail Pilot a reality. That’s over $1,500 a day.

With 3 months to go before graduation, $54k in the bank, and now a job offer from 1,623 fans of my ideas, I couldn’t wait to go full-time. If I didn’t have senioritis before, I definitely did by then. (Honestly, I probably had senioritis since the fourth grade.)

By June, we launched the first backer beta. In September, we launched the first publicly available version of the product — a web app.

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This launch went so well — quickly making more than the Kickstarter campaign — that some pretty big people started reaching out. Most notably, Apple.

When asked if we’d be available for a call, I believe my immediate response was “whenever you call this number I will answer halfway through the first ring.”

Someone that handles Apple’s promos on the App Store editorial team asked us if we were considering bringing Mail Pilot to their platforms — iOS and Mac OS X (as it was named at the time). We were of course already planning on it, but with their recommendation, we re-prioritized iOS over Mac.

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In April 2013, we launched Mail Pilot for iPhone and iPad. Apple featured it on the front page of the App Store (at this point I was certain we had peaked, and it was all downhill from here).

Along with a Techcrunch article, this was a stereotypical startup launch success story, but it wasn’t without one large snafu that I wrote about recently.

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In January 2014, we launched Mail Pilot for Mac.

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This launch might look the same, but it was very, very different. It was featured with a banner, and listed as a best new app, but look in the bottom right corner. It became the #1 Top Paid app in the entire Mac App Store within hours of debut. It took that spot in over 50 countries by the end of the year. It took that spot in its category in an additional 40 countries.

This was a whole new world for us.

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In 2016, we launched an entirely new product, Throttle. It took the #1 spot on Product Hunt the day it launched, quickly joining the 1,000 club along the likes of the Tesla Model X.

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Do you remember how we got here?

Back up five years. Even if you’ve read this whole story, you may have forgotten: this began when an unknown and inexperienced, but eager and ambitious undergrad decided to give Kickstarter a go with a strange idea to solve a tough problem in a new way. That’s it.

If you’ve been considering starting your own thing, creating and selling your own product, starting your own business to solve a problem you see in the world or your local community, then hear this: don’t worry about all the reasons why it probably isn’t possible, or all the things that might be going against you.


How You Can Do It Too

If you’re in the beginning or middle of your side-hustle, or a full-on startup, I’d love to chat. I promise I’m not selling anything; I enjoy mentoring the startups I’ve been connected to locally, but I’d love to see if I can help entrepreneurs and founders globally that have been reading these articles, and that need a sounding board. I’d love to schedule 30 minutes to discuss what you’re working on. Just shoot me an email.

If you’re not ready to chat yet, just subscribe to my newsletter. Every Thursday, I’ll send you a new article, which will also serve as a reminder for when the time is right to shoot me an email so we can hop on the phone.

I also just moved to Chattanooga, Tennessee, so if you’re in the area, let’s grab coffee.

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September 6, 2016 - No Comments!

Drive After Audacious Goals Without Regard For Their Improbability

I almost titled this article “We’ve Lost Our Naivety”. Here’s why:

As a senior in college, with no experience and no network, just a love of product design, I decided to start a company. Why?

In a course I was taking senior year — Design of Information — I hadn’t kept up with my “design journal” before the first journal check. Needing to fill 10 pages in one night, I picked a topic so hairy and difficult I figured it’d easily fill the minimum page requirement. That topic? Email.

By page 3 I was in love with what I had sketched. It captured every ounce of my fascination. It made so much more sense than anything I had seen before.

After months of discussing the idea with people and iterating on it, we turned to Kickstarter. This was January 2012. My life changed entirely that month.

Knowing no one in the industry, having no prior experience, no previous work to prove my credibility, no existing audience to leverage — just Photoshop, Xcode, and a passion for thoughtful and empathetic product design, we launched a Kickstarter campaign with a goal of raising $35,000. If that doesn’t sound impossible yet, it’s also worth nothing that no closed-source software project had raised that much on Kickstarter, let alone one from some no-name undergrads.

After 5 weeks, a feature in the New York Times as “Ingenious” and WIRED Insider’s Kickstarter of the Week, with praise from our idols such as Jason Fried, a “Staff Pick” listing on Kickstarter, and most importantly, with 1,623 backers, our humble Kickstarter campaign succeeded with over $54,000 in funding.

We went on to follow up the campaign with a handful of even more surprisingly successful launches.


Someone recently asked me what the key ingredient was.

Honestly, I think it was equal parts excitement for an idea that we really believed in, and thought should exist in the world, and naivety — not knowing just how impossible it was. We’ve been able to bootstrap the business for years since that Kickstarter campaign. If we had laid out what has happened the last four years as our plan back in 2012, and asked some pros in the industry what they think, they’d laugh us off.

We embarked on the journey because we didn’t know it was supposed to be impossible; we were blinded by ambition, and enabled by naivety.

The problem we have now is we aren’t naive anymore. I hear us more and more saying things like:

“No, there’s no way that’ll work”

“It takes years to build up an audience to do that”

“Big Company X invested hundreds of thousands to launch their podcast, there’s no way we could get close to their level of success”

“The best content marketing strategies are executed by teams in companies dedicated full-time to writing and publishing, we shouldn’t even try.


We’ve lost our naivety.

Our new secret to success, one I hope you’ll embrace in this new age where things that seem daunting are secretly possible, is a new focus:

Drive after audacious goals without regard for their improbability.

I write this primarily to myself, but maybe you’ll glean some value from it too.

The only people that find out impossible goals aren’t impossible are the ones who try to achieve them. If you know too much, and you’ve become cyncial — if you think of all the things you don’t have to achieve the things you want to do, if you’ve found yourself walking down more and more traditional, mediocre paths, then I’ve got a message for you:

It’s time to embrace willful naivety.

Your successes, failures, and everything else you’ve learned to get to where you are now are holding you back. Embrace the naivety that got you started. Drive after audacious goals without regard for their improbability.


If you want to follow on this journey with me, as I willfully return to the naivety that got me started — so that we can once again embark on impossible goals, then subscribe to my newsletter. I’ll send you a new article every Thursday, and soon enough, a book on product design and innovation.

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February 25, 2016 - No Comments!

My #1 Job as CEO

The Virginia Tech Corporate Research Center asked me to write a post for their “Business Brief” column, where they ask CEOs “What key lesson have you learned in business that would help others?” I’m cross-posting my answer below, but you can read the original on their website.


Ihave learned a lot since starting Mindsense, and another company before that. I’ve learned I need to trust my gut more; we’ve made some bad moves by following the advice of those that are high up in our industry (partners at Apple, prominent investors in our niche, etc.), where looking back on it, my gut would have been the right way to go. I’ve learned that maintaining strong relationships with journalists and bloggers can give far better results than paying for ads (we don’t spend a dime on advertising). I’ve learned that we don’t need to fear copycats long-term (a team that ripped off our first product sold to Dropbox within a month, but was ultimately shut down). I’ve learned that, as my in-office team grows, my most focused work gets done before I get to the office. I’ve learned that you can totally bootstrap a company like ours (we started on Kickstarter and have operated on product revenues since).

But I don’t think that I have enough experience to deem any of these lessons I’ve learned as universal truths to give as advice to others. They’re interesting experiences that I’m happy to share, but the lessons themselves are fairly one-off.

However, I think there is one lesson that I can share, and to me, it’s a big one. It’s how I’ve naturally always approached starting a company, forming a team, and driving after big goals; but after chatting with folks at similar companies, I’ve learned that some of our approach can be unique.

At Mindsense, everything is centered around people: our purpose is to solve unsolved problems to improve people’s lives; our mission is to improve the lives of the people that use our software, work on our team, and live in our communities.

The wrong people with the right idea won’t be able to execute on it. The right people going after the wrong idea will get there; they will figure it out.

Our team is small (4 people), so the lesson is exponentially real for us. We need to have the right people on our team. I presume, but cannot prove, that at a larger company, it’s equally true of your executive team. It’s all about the people.

The most important thing I need to do is make sure we have the right people, that they are properly supported and resourced, that they are motivated and fulfilled by the work they have, and that the team is well balanced and covers all the strengths we need.

Having the right people is the most important thing for our success.

Often, I am asked to share some of our biggest challenges. I realized, over the years, that our biggest one was right at our inception: we didn’t have all of the strengths we needed on our founding team. Particularly, while I am a good software developer, I am not a great one; it’s not intrinsically motivating to me, so I will inherently do a poorer job than someone else who is deeply passionate about software development, and therefore more thorough with it.

Yet, for the first 2.5 years of Mindsense, I wrote all of our software (barring our first summer when a co-founder from a previous startup volunteered his time on nights and weekends to help out). I was our only software developer, and not only was I only good and not great, but I didn’t even get to be full-time on development; I’m also our only designer, our only marketer, etc. While we were able to launch our products from that time eventually to 50,000 customers, since they were technically inferior, we incurred a lot of time debt on maintenance and support.

We ended up with mediocre execution on top of publicly touted “ingenious” (David Pogue, in the New York Times) ideas. This was a big stumbling block for us when we were just coming out of the gate.

After 2.5 years, our first full-time software developer, Jeb Schiefer, joined the team. He is the exact opposite of me as a developer: he is meticulous and detailed; he isn’t finished until he has written unit tests, and what keeps him up at night is our software stability. He is passionate about software development, and it makes him a great software developer. We hired him to have him lead engineering on our next big project: Throttle. And the difference could not have been more evident over the last few months as we’ve launched Throttle: we’ve brought on 10,000 registrations, but never had a difficult or stressful launch, there were no show-stopping bugs that popped up, and customer support has been easier than ever. This had never been the case with previous launches.

Having the right people on the team makes all the difference. It’s what moves us from good to great. One way we ensure a balanced team is by thoroughly using Strengths Finder. Every new team member at Mindsense gets the book as a gift, takes the online test, and has their strengths on a plaque on their desks. You’ll notice, as you look around the room, strong complements between our strengths. Not only do we learn more about ourselves through our strengths, but we learn how better to work together; how to communicate with each other more effectively, when to lean on another team member to navigate around one of our own weaknesses, etc.

But because each person is so important to the overall mission, caring for and supporting the people on our team is my number one job.

We promote personal autonomy quite a bit (if you haven’t read Daniel Pink’s Drive, it’s fantastic). We have no core hours at Mindsense. Instead, at the beginning of the week, we outline what we all need to get done. At the end of the week, we demo what we’ve worked on. If anything didn’t get done, we have to take responsibility for why. But as long as the work gets done, it doesn’t matter if a team member needs to leave Wednesday at noon to run errands, or doesn’t come into the office until 10. We’ve had team members that are more productive in the afternoon come in and stay later, and team members that are more productive in the morning come in and leave earlier. We even have a minimum vacation policy, rather than a maximum.

This doesn’t work for everyone — some people can’t manage themselves, so not everyone has lasted. But on such a small team, we don’t have the time to manage people anyway, so if someone needs a manager to be held accountable, it’s a mis-match from the start. With such an extreme level of autonomy, people self-select quickly.

Instead of spending time managing people, I’m freed up to support and motivate people. Rather than leading from above, I lead from behind; instilling in team members our core identity as a team, and our envisioned future, and I support them as we all carry our flag forward in the direction that we see fit. We first huddle; aligning onto a common purpose and goal, then the entire team works together to get us there. I’m not the head coach; I’m the team captain.

We push hard toward extreme goals, so we’re high-energy, but we’re also high-purpose. This is one way we ensure team members are motivated and fulfilled: with a strong sense of purpose (if you haven’t read Jim Collins’ Built to Last, that’s another must-read). Mindsense exists to improve people’s lives by solving unsolved problems in human-centered, innovative ways. We write this purpose on the whiteboard before every big brainstorm or meeting. It’s the first thing you see when you log in to our team intranet. Every major decision we make after first asking if it moves us closer to our core purpose.

It’s the unsolved problems that intrigue us; these are the problems that get us up and motivated to get to work each day. They’re an addicting challenge. They’re so ambiguous that they require deep empathy, thinking from many different perspectives, and a-game brainstorming; but with all three, we can invent incredible new human-centered solutions that really knock it out of the park.

My role is not to light a fire under people. My role is to light a fire in people — to paint a picture of the future, and fight alongside my team members to get us there.

By doing all these things, we’ve found that we can foster an environment that motivates people to get up in the morning to come to work, and leaves people feeling fulfilled at the end of the day.

When I was preparing a keynote for the Virginia Tech Leadership in Engineering Conference, I asked Jeb a little about that. He put it this way:

“The environment we’ve created at Mindsense where I can use exciting technology to build useful software for other people makes me look forward to coming into work every day… I had always felt like I was a part of something bigger than just a 9–5 job.”

Notice he said “the environment we’ve created” — it’s something that he has a sense of ownership over; his input matters, and he can mold Mindsense into the company that he, along with the rest of his team members, feels should exist in the world. This level of personal buy-in is incredibly fulfilling.

He also said “for other people” which has strong ties to our purpose. You can immediately see the effect that has in his last sentence, “I was a part of something bigger than just a 9–5 job.”

Mindsense is made up of people. Great people make a great Mindsense. My number one job is to find and support great people.


Originally published at www.vtcrc.com.

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January 26, 2016 - No Comments!

Your Startup Needs a Coxswain

On a small team, everyone’s rowing. There are no “managers” — there’s only room for rowers.

First, understand that rowers face backwards (the joke on our team in high school was that crew is the only sport you win by sitting down and going backwards). Rowers do not see where they are going.

Second, understand that you win a race not on any individual’s skill; the team whose rowers are most in unison will win. Watch a few clips in this video if you don’t know what I mean.

See how they must be perfectly in sync to beat the competition.

As a startup founder, I’m rowing with my team every single day. And I think that’s an important part of being a good leader. But I cannot forget, even when there’s a million things to be done, that my team needs a coxswain.

The coxswain fulfills two very important functions: steers the boat, keeping it safe and on track, and sets the pace to keep everyone in unison, providing motivation to push harder as needed.

A boat without a coxswain would not be in sync; and rowers out of sync will lose the race.

But the coxswain is also the only person facing forward — the direction to which the boat is quickly moving. Without a coxswain, rowers would only know where they were rowing to once they got there.

As a team leader, it’s up to you to identify leading metrics and project into the future to see, in advance, when your team is headed towards a crisis that could be avoided entirely with a slight change in direction now. A team without a coxswain is just like a crew without a coxswain: the team only knows where they were headed once they get there. Crises have a way of sneaking up on these teams.

It’s also up to you to set the pace, keep the team in unison, and ensure everyone is properly motivated. This gets harder as your team grows; poor communication causes different team members to execute towards slightly different goals.

Who is the coxswain on your team? Are they taking enough time out of the day-to-day to be the team’s coxswain, facing forward and looking far along your current trajectory?

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January 5, 2016 - No Comments!

Mindsense: 2016

It’s about time. I owe you — our fans, followers, and customers — a big status update on all things Mindsense. I’ll kick it off with our successes and challenges of 2015, then talk about where we’re headed with Mail Pilot and Throttle, and give you a few company-level updates.

Mail Pilot

Many have asked, inevitably, if our time investment into Throttle means we’re abandoning Mail Pilot. Not at all — quite the opposite.

Successes in 2015
Heading into the year, we were putting finishing touches on Mail Pilot 2 for iPhone + iPad. We had a record high of four developers on the project for months.

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We were elated after having achieved goal #1: get good ratings

We rewrote the thing from the ground up. We totally reimagined the navigation system (the bedrock every mobile app needs to succeed) to leverage how users live in the inbox and primarily just triage on the mobile. We designed new interactions for quick organization. We made it super customizable. It was the third email client we had built from the ground up, so we felt pretty good about the basics. We went to a ton of effort, spent a ton of time and cash, all with one primary goal: get good ratings.

The success? After releasing version 2.1 to address a few minor issues, we averaged 4.5 stars in the App Store. This was a major victory.

We also launched Mail Pilot 2 for Mac with Dash, an all-new view that users have written in to let us know it has already become their default view. It was a bit of a passion project; something no one was asking for, but something we’ve always dreamt of and sketched out. We wanted to get it into Mac 2 because it’s fun for us and the users, and it continues to break out of the mold of what email clients “should” look like.

Dash in Mail Pilot 2 for Mac

Dash in Mail Pilot 2 for Mac

Challenges in 2015
As we would learn from our admirees (what’s the word for that?) at Panic, mobile just isn’t the way to go for us, either. Maybe it’s our category (productivity). Maybe it’s our target market (productivityists). But one thing is for certain: the revenue just isn’t there. Under a third of Mail Pilot revenue is from mobile. Specifically, it’s at 30% to date.

Unit sales and revenue breakdowns for mobile versus desktop sales of Mail Pilot.

Unit sales and revenue breakdowns for mobile versus desktop sales of Mail Pilot.

While almost half of our unit sales have been mobile, under a third of our revenue has been on mobile. To make it worse, people regularly tell us our iOS app ($9.99) is too costly, and our Mac app ($19.99) is too cheap. Our numbers aren’t as dramatic as Panic’s we’re, but the lesson is the same: people looking for what Mail Pilot provides want to invest in their desktop email experience, but not nearly as much in their mobile.

For about the entire first month of Mail Pilot sales (our biggest revenue period), we only broke even on paying for an outside contractor to join our development team for the last few months of the project. This was a big loss for us, and a hard-learned lesson: the numbers just aren’t there on mobile for us.

This makes it really hard to justify investing into mobile for Mail Pilot. We want to; we’re incredibly proud of the product we put together for mobile, but the numbers just aren’t there. Going forward, we’ve been looking at mobile offerings for future products being more like mobile “companion” apps than full-fledged clients with feature parity. But note that nothing here is set in stone; we’re always eager to learn and adapt.

Where to in 2016
We’ve got some really incredible ideas and prototypes for where Mail Pilot is going next. We’re working on some really cool stuff that no one has attempted before; it takes even more leaps and bounds ahead than the initial Mail Pilot concepts did in January 2012.

These new innovations and directions will make up the third generation of Mail Pilot, but I don’t think it’ll be called “Mail Pilot 3” — I have a feeling it’s going to get a totally new name, though still under the Mail Pilot umbrella.

When will we start unveiling the third generation of Mail Pilot? I have no idea. In many ways, our prototypes have been too ambitious — we’ve put together 3 functioning prototypes already to date, each of them very different, and each of them very ambitious. The hardest part is figuring out how to scale the concepts back so that it’s shippable.

In the meantime, we’ll still be shipping updates to Mail Pilot 2. Most recently, we launched update 2.3 for Mac to fix a ton of crashes, mostly related to Dash. We really dropped the ball on ensuring stability on it, because we rushed the feature out too quickly (for that, I am sorry). But we combed back through it and put it on a much more stable foundation in 2.3.

Throttle

We unveiled our first product outside of the Mail Pilot brand mid-year. It’s a really exciting product, because it brings a lot of firsts to email users. In particular, it solves email’s biggest problem in a totally air-tight way for the first time.

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Why Throttle?
It represents exactly what we’re all about: solving unsolved problems in innovative ways to improve people’s lives. We’ve come up with plenty of interesting ideas, but usually there’s someone ‘close enough’ or already solving the problem pretty well. It’s the unsolved problems that intrigue us; these are the problems that get us up and motivated to get to work each day. They’re an addicting challenge, and they’re so ambiguous that it requires deep empathy, thinking from many different angles, and a-game brainstorming. When we came up with the core concept for Throttle, we knew we hit one of these for the first time since Mail Pilot’s inception. While many interesting ideas are on the scrap floor at Mindsense, we knew we had to breathe life into Throttle immediately.

Why SaaS?
It represents the kind of relationship we’d prefer to have with our customers. With our Mail Pilot sales on the App Store, we’re selling one-time paid apps in a market where customers expect apps for free or $0.99 with support and updates for life. If a customer buys our app for $10, we take home $7. If they email support just a handful of times over their lifetime of using Mail Pilot, we lose money on the whole thing. So the incentives are backwards: we’re financially disincentivized to tend to a customer after a sale is made, which is the exact opposite of what we want to stand for.

We want to be a good steward and an equal partner in our relationship with our customers, and SaaS is a great way to flip the motivation. With SaaS, you worry about keeping retention up, so you’re constantly incentivized to tend to all of your current customers. Instead of losing money, you make the money you need to continue to operate by caring for customers, offering great support, and shipping innovative new updates. SaaS makes being a good partner to our customers sustainable. And if we can’t pull it off — if being a good partner can’t be made sustainable; if going the SaaS route doesn’t work — we don’t want to be in the relationship in the first place; we’d rather go out of business than be a poor team to have a relationship with.

Where to in 2016
A lot of things are on the horizon: first, we will launch out of soft launch, then we’ll start to release Throttle Pro, Throttle Mobile for iPhone & iPad, and a few other interesting products into the Throttle ecosystem. We’ll give early access to the first thousand customers that request the Throttle Mobile and Throttle Pro betas.

Keep an eye on Throttle this year, and let me know if you have any thoughts and ideas on it; we’re iterating quickly.

Making Mindsense

Finally, at the end of 2015, I doubled-down on that whole ‘content marketing’ thing. I never touched it because I didn’t want to do it simply for marketing’s sake, I needed a better purpose but didn’t have one.

That all changed when we sat down for a “Built to Last” style company retreat and refocusing, where we set a 20-year BHAG to become the company known for being the best at innovating; the best at solving really hairy unsolved problems in innovative ways to improve people’s lives.

Making Mindsense, a new behind-the-scenes look at Mindsense

Making Mindsense, a new behind-the-scenes look at Mindsense

At making.mindsense.co, I’ll be regularly publishing project updates and articles on innovation, design, productivity, small business, and leadership. Much of it will be a behind-the-scenes look at how we do things at Mindsense, such as in my most recent article on how we innovate.

Team & Company

We’re still in the two-room suite we moved into in 2012 and expanded in 2014 in the VT Corporate Research Center, just behind our alma mater’s campus (and, more importantly on six Saturdays in the Fall, Lane Stadium).

We’re still a strengths-based team, and our purpose is still the same. But what’s new in 2016 is that we’re intentionally making the move from being a product to being a business — a lasting, sustainable company. It’s a shift I only hope we do with some amount of grace.

We’ve always been incredibly fortunate to have you, our biggest fans, who read all the way down to the bottom of what I can only assume are increasingly dull blog posts, and who stepped up to make Mail Pilot a reality nearly four years ago on Kickstarter when no one had heard even of us. So, in a big way, thank you. And happy New Year!


Here’s to 2016.

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November 11, 2015 - No Comments!

Three Qualities of Entrepreneurs That Aren’t Clichés

Regularly, students ask me about what qualities make good entrepreneurs. There are too many cliché answers I could give, so over time, I’ve built up my own list of three that aren’t cliches:

Impatience

When I looked at my designs for an ‘email client of the future’ I wanted it immediately. I didn’t want to wait for someone else to figure it out, my impatience was such a huge motivator that it pushed me to sit down and make it happen as soon as I could.

Naivety

Without naivety, it’s painfully clear just how much work, energy, and time it takes to start a business, or build an entire line of email clients from scratch. So I think naivety really helped me: I was able to jump right in without reservation.

Empathy

When it comes to designing products that are successful at fitting right into place in a person’s life, workday, or environment, it starts with empathy. You have to be able to get into the mind of your potential customer and figure out their language, motivations, goals, working styles, etc.

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November 10, 2015 - No Comments!

The Human Element of Great Leadership

The Difference Between Good vs. Great Leaders

I’ve been asked a few times recently to give advice to leaders. I have usually responded by saying that I don’t have enough perspective or experience to have distilled any universal truths that would be credible advice that I think someone else should take. That said, the question keeps coming up, and there are probably a few words I can string together on the topic.

What I can share are lessons I’ve learned for myself. I’m not suggesting anyone take these lessons as advice for themselves, but these experiences that I’ll share may help direct your own thoughts in the future. Here it goes.

Have no ego

To be a great leader, I have found that you must have no ego whatsoever. Leaders with egos need to feel more important, smarter, needed. This is toxic for a few reasons:

  1. Leaders with egos hire people that aren’t as good as they are. The entire team underperforms because their leaders cobbled together the wrong team. This is where the saying “A players hire A players; B players hire C players” comes from.
  2. Leaders with egos ensure that people need them. For example, they might hand over most of the reigns, but keep an important step for themselves, so people have to keep coming back to them. Why is this so bad? Well, a team that would crumble without any one single member is a team hobbling on one leg.
  3. Leaders with egos don’t allow a winning ideology to permeate the team, so their team lacks a basic cohesion, depth, and alignment. Instead, people work “for” him. These leaders prefer to be the charismatic, well-known, potentially genius face of the team instead of supporting and resourcing their team members with a unifying purpose and method for success. This means they aren’t succession planning — so when they go, any performance the team was able to achieve before won’t last very long.

Lead from behind

Don’t manage people. If someone can’t manage themselves, they probably don’t belong on our small, high-passion, high-energy team. Making more rules tethering people to their desk at specific hours of the day, telling them how many days they are allowed to not be at the office per year, and telling people exactly how to do their job are all ways of managing people. People that should already know how to handle all of those things (time management, how to do their job, etc.) on their own.

Rather than leading from above, I ought to lead them from behind; instilling in them our core identity as a team, and our envisioned future, and supporting them as they carry our flag forward in the direction we all see fit. We first huddle; aligning onto a common purpose and goal, then the entire team works together to get us there.

Motivate with Purpose and Goals

In my experience, it’s much more effective to motivate not with carrots and sticks (rewards and punishments, see Drive), but rather with a meaningful purpose and audacious goals.

If I told you, “we’re going to build this thing over the next year, and if it succeeds, I’ll give you a 5% bonus, but if we start to slip, we’ll lose vacation days” how would you react? Would it motivate you? How much?

If I told you, “we believe that people should get to control who can send them email. We believe that people shouldn’t have to waste so much time in their inbox with pedantic tasks. We believe that we can improve people’s lives by freeing up their time for more important things — meaningful work, time with their family, etc. Because of this, we’re going to topple the biggest incumbent in the email industry with the innovation that we’re pulling together over this next year.” How would you react? Would it motivate you? How much?

My role as a leader is not to light a fire under people. My role is to light a fire in people — to paint a picture of the future, and fight like hell alongside my team members to get us there.

Fight alongside your team

I think many poor leaders think of themselves as head coach, when they should think of themselves as team captain.

A friend of mine, a CEO at a young company, went through tough times and a few team members left the team. Instead of demanding the other team members work more until replacements could be found, this CEO hopped right into the assembly line alongside the rest of the team and help get the products out the door on time. This CEO, along with ever member of their team, understands their common purpose and their common goal, and they’re working together to make it happen, regardless of the circumstances.

Motivation and Fulfillment

By doing all of these things, we’ve found that we can foster an environment that motivates people to get up in the morning to come to work, and leaves people feeling fulfilled at the end of the day.

Our lead developer at Mindsense, Jeb, put it this way:

The environment we’ve created at Mindsense where I can use exciting technology to build useful software for other people makes me look forward to coming into work everyday… I had always felt like I was a part of something bigger that just a 9–5 job.

Notice he said “the environment we’ve created” — it’s something that he has a sense of ownership over; his input matters, and he can help mold Mindsense into the company that he, along with the rest of his ream members, feels should exist in the world. This level of personal buy-in is incredibly fulfilling.

He also said “for other people” which has strong ties to our purpose. You can immediately see the effect that has in his last sentence, “I was a part of something bigger that just a 9–5 job.”

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