Tag Archives: pressgram app

Life and Entrepreneurship with Pat Flynn and Tony Stubblebine

In episode 80 of Smart Passive Income, Pat Flynn interviews Tony Stubblebine, CEO and co-founder of Lift.  Lift is an app that allows users to track small actions that lead to larger goals on a daily basis.  .

The interview starts with a summary about Tony’s career before starting Lift. (6:15)  

I had been bootstrapping my own software company for a long time before Lift, and the first three years were just incredibly hard and difficult.  I had so much work and so little money,  but somehow in year four it just completely flipped.

Tony is one of those people who suggest that it’s going to take three to four years to get your project going and lifted off the ground.  As this happened for him, he was able to hire more people that did the work for him and he created a “passive income stream,”  but in doing so this led him to question what was next.  

In moving from this first startup to Lift, Tony said he was looking for something to pursue that involved human potential, “I got something that I was personally interested in and that I enjoyed.” (7:15) Tony realized that he wanted his next project not to be just about software, but also about living better.  He started Lift then, to scratch his own itch.  Finding a problem and solving it is something that John Saddington echoed when he started Pressgram.  About the desire and conception he wrote: “In a dimly-lit Cuban-Mexican joint I drafted out an application that would satisfy my desire for digital publishing and filtered photos. No obvious solution had emerged that I was satisfied with. That itch was now begging to be scratched…”

Lift is a tool people use to help tackle their goals through habits, and do in a small way each day.  Part of what makes habit formation possible is removing the decisions we face towards whether or not we do them.  I don’t want to run or write or code or read, but when those things are on my phone, popping up as alerts I can respond to them.  We’re removing the option not to do them by including them on a device we like to do things from.  When a Facebook alert pops up or an email gets sent to you, there is a mental rush that people want to say something to you. I suspect that this plays a role in the success of the Lift app as well.  

Tony also mentions in the interview (9:45) that it’s important to break things down into small steps and make regular progress toward them. Run a marathon or build a website are not habits, but run a mile and write code for 20 minutes are.  Lift allows users to break down their large goals into achievable habits and do them in a specific way.  

In a March, 2013 TEDx Talk, The First 20 Hours – How to Learn Anything, Josh Kaufman talks about breaking new skills down to the smallest portions.  Take the running example again.  If you want to run a marathon first you have to run ten miles, but before ten you must run one.  But before you even start running you need running shoes and make time for running.  You find the smallest steps and do those.   For Josh this came when he was trying to learn the ukulele.  Having never played before, and not knowing where to start, Kaufman tried to find the most important parts of playing.  In his search, he found that there were four chords that accounted for almost all the songs he wanted to learn and that was all Kaufman really needed to know. Don’t believe it? Well most pop songs are just four chords.  

Returning to the interview, Tony talks about the things Lift can do, Pat tries unsuccessfully to guide the conversation back to focus on entrepreneurs and what they can learn.  To Tony, it’s about getting your life in order before you can be successful at anything. He says, “entrepreneurship is also about balance, if you don’t have the rest of your life in order it starts to intrude on your work and it starts to drag you down.”  (12:45)  In Choose Yourself!, James Altucher writes the same things: (page 32)

But in order to have a fully functioning life, we need a functioning body, a healthy brain, a functioning social life, a functioning idea muscle, and a very fundamental sense that there are some things we can’t control.

Why is this so important?  Why can’t you just bear down, lose focus on your friends, family, and fitness?  Tony says that if you get to this point, “you’re not qualified to be an entrepreneur anymore.”  This happened to John Saddington, founder of Pressgram mentioned above, he writes: “My body was calling it quits and I don’t blame it as I was attempting to finish out a double Master’s degree, exit a startup that I had started with my brother, make a significant pivot with another venture (including a possible capital raise), as well as develop a secret project that had eventually became a major focus for the next year.”  That secret project became the Kickstarter for Pressgram and John righted his non-business ship, including removing 27 pounds.  

Besides having your life in order, Tony’s other tip is to know what the key parts of your business are, “it’s much more important to figure out the one thing that really matters and be aware of when this happens and be ready to grab it.” (14:00)

Some call this serendipity,  on the Tropical MBA podcast, John Myers says to “be the engineer of your own serendipity”, in Manage Your Day-To-Do Scott Belsky does this by unplugging and opening himself up to serendipity.  

About half way through the episode (19:15) Pat starts to wonder what would happen if Lift had a penalty feature.  If you don’t do one of your habits, then ten cents is deducted from your bank account.  Tony says that this might work, but the research his team has done suggests that in the science of behavior design, positive reinforcement might be a better tool.  They’re trying to get people to do one thing on a consistent basis, they’re using the carrot instead of the stick to get you to eat your carrots.  

Besides positive reinforcement, Tony says that small progress is important, and small progress is Steven Pressfields’ first step toward turning pro. Pressfield writes that the first step toward going pro is to do something for one hour.  Leo Babauta at Zen Habits writes that one way he built the habit of flossing, was to floss just one tooth.  In Daily Rituals there is this quote from Joseph Heller, “If I write a page or two a day five days a week, that’s 3000 pages a year and it does add up.”  

What sort of insights then has Tony gotten from running Lift?  There must be a treasure trove of productivity hacks for entrepreneurs for dealing with email, late nights, and travel right?  Nope.  The first and only insight he mentions is how to meditate more.  (26:10)

Tony says that many entrepreneurs work on meditation and that it’s helped him personally.  (28:15)  Being aware of how he’s feeling lets him switch from task to task and remain engaged with them.  He gives the example of ripping through his email inbox and then jumping over to do an interview with Pat and then immediately after being interviewed, he’s interviewing a designer.  

Tony isn’t the only executive who find that motivation is helpful.  In Be Excellent at Anything, Tony Schwartz and his team share that meditation has helped a lot of executives even though many were reluctant to try it.  They share why one CEO started meditating: page 202

I didn’t start meditation because I was interested in higher states of consciousness. My goal was practical. My job involves dealing with all kinds of different people and activities, and it’s hard to stay focused on any one. I’d always find myself ruminating about the last meeting or anticipating the next one. I took up meditation because I wanted to see if I could learn to slow down my mind.

Schwartz and Stubblebine both suggest keeping meditation short – two minutes – and use one of two techniques.  You can focus on your breaths and count them as they go in and out or you can be mindful of whatever pops in your head, but let it leave as easily as it comes.  The same CEO shares his thoughts on mindfulness or mindful meditation:

Breath counting was fine, and it really helped me, but it wasn’t very interesting. Mindfulness was much more intellectually engaging. It was fascinating to actually learn to observe my own mind the way I might watch a movie or a play.  It was a revelation to discover that I could observe an emotion – anger or frustration or irritation or even sadness – without feeling like I had to react to it. .. I got so I could name it and then just watch it pass by.

Along with meditation Tony shares one other tool, a script.  Scripts allow us to not have to convert mental energy to something that doesn’t require it and allows us to consistently make the right choices.  Dan Andrews at Tropical MBA talks about personal and professional scripts often.  

Tony’s script is for telemarketers when they call and it goes like this. (31:00)  “Thank you so much for calling, (pause) but we’re not interested, (pause) goodbye.”  He says that the pauses are there to give them a chance to say goodbye and to Tony, he was polite and this conversation fit the pattern of normal, non-irritating conversations.   It’s also automatic so he doesn’t need to think about what to say about getting out of the conversation and the script prevents a swing of emotions because the call was irritating or frustrating.

Tony and Pat end the conversation with two more practical tips for entrepreneurship.  Tony suggests that if you never take money from somewhere you owe, you’ll never go out of business.  For him this meant consulting on the side until he had enough to pay himself, then after getting enough to pay someone else, he did.  He suggests not taking out loans or to mortgage your house because those are the things that will knock you out of business.  

His second tip is that you need to put in the work and care about what you do. This part of the conversation tip-toes along a line that Cal Newport says might not exist, but Tony’s point is less about pursuing passion and more about pursuing something.  It took him three years of hard work at his first startup and he had to do that every day.  And if you do find something you love doing, then that will be your hobby.  Tony ends the interview with a story.  At his old job he was working and saving and working and saving some more so he could buy a new television.  He spent three months looking for the best reviews, comparing models, and saving money from his job.  Finally he bought the television, but how much does he use it now?  “Almost never.” (35:20)  Now his job at Lift is what matters most and that’s what he wants to do.  

I chose to go back and take notes on this interview because it demonstrated the blending nature of life.  Your job and life are not mutually exclusive.  Everything we do affects the other things in our lives.