Productivity Hacks: Founders’ Approaches to Superhuman Production

From old-school habits to the tools of the future, Founders discuss where their own productivity hacks and why they work for their startup.

June 8th, 2017   |    By: Keith Liles    |    Tags: Management, Productivity, Startups Live, Strategy

It’s taken on the allure of the holy grail. Systems would crash trying to count the words devoted to the subject. I’ll bet you don’t need to be told that I’m writing about: productivity.

We’re all in search of greater productivity (even if we define doing less as more, make sense?) One day, the times we’re living in may well be known as the GSD era.

Notes, doodles, end-of-day/beginning-of-day routines, virtual assistants… Buckle up as Startups Live surveys Founders’ different approaches to achieving superhuman productivity.

Productivity Hacks

Wil Schroter wasted no time diving into a conversation that several people proved eager to discuss. “I’d like to talk about time management, but I’d also love to talk about how you all are managing productivity.”

“I like writing down my top 3 tasks on a post it at the start of each day,” said Eileen Guan. “That way I don’t get distracted and not finish what’s important!”

“This is a nice continuation of our chat from yesterday re: more hours = more output?” noted Ryan Rutan.

“One of the things that I forced myself to do a long time ago (to cope with my insane ADD), was to open up a doc and write down everything that was in my head as my first order of biz each day,” divulged Wil.

“I found that if I ‘cleared the hard drive’ of all that stuff floating around it would allow me to stop thinking about random stuff and focus on the top tasks.”

“Prioritization has always been key to my time management,” said Ryan. “Especially in the startup world, where things can come at you fast, being able to avoid getting sucked into reactive mode is critical.”

“I’m a rampant to-do lister,” offered Dan Rockwell, “tho I think the real super power is the random doodle per day… lol.”

He had a big following, both in fellow listers and fans of his doodles. (More on that soon…)

“I’m a ‘eat the frog’ kind of worker,” Lauren Tiffan put out there. “Has anyone heard that reference from Mark Twain or read the book Eat That Frog?”

“The concept is to just get the big to-do out of the way in the morning… it’s gonna be gross and tough, but if you get it over with and stop procrastinating, you free up your mind and time for the rest of the day…”

I.E. – start with the least desirable task “and the worst part of your day is over already!”

“Do you guys find that your hardest task is easiest to do first? Meaning the beginning of the day is the best time?” Wil asked.

“I think it’s often hard to get started, but once I get into the task, it’s much easier to stay focused earlier in the day.” [Eileen]

“I typically knock out one simple thing to make me feel accomplished (even if it’s just making my bed in the morning), then tackle the big guy.” [Lauren]

“I tend to go the other route – get all the little stuff out of the way so I can get after the big thing without any distraction later.” [Tim Allen]

“For me it depends on the type of task – we talked about it a bit yesterday – I have periods throughout the day where I am better at certain activities. If it is creative in nature, afternoon or later is best. If it’s grind mode, analysis, or something nerdy, morning is best.” [Ryan]

“The biggest/most important thing on my plate is usually the most motivating, so I definitely prefer that tackled first!” [David Krock]

Feeling lonely with Tim Allen? Wil falls into the same camp. “I try to clear the decks as much as possible only because the big task often requires an entire day.”

Tim followed up, saying, “the big ones usually require more concentration, so that just works better for me.”

Ryan wasn’t convinced, and pressed Tim and Wil, “Why not just start with that then – so you are sure you can get through it? Why sweat the little things?”

Tim replied, “For me it’s just a matter of eliminating all the distractions.. that list can weigh on you if the list of small things grows and grows while you’re doing the important stuff.”

Wil’s mind zagged in a different direction. “David, what’s the biggest task on your plate today? (if you don’t mind sharing). Mine is re-writing our homepage copy.”

David answered, “Deciding whether to scale my collection of wedding businesses (currently a profitable $1.2M in sales) or keep as-is (with associated simpler lifestyle).”

“Oh boy,” exclaimed Ryan – “these are the best kinds of problems!”

“When we’re small, all we care about is getting paid. When we get paid, all we care about is not being small,” said Wil.

And at last, the first dry erase marker doodle appeared!

“I’m picturing you with a beret coloring Bob Ross style as you think about your day,” commented Wil, then kept the talk on the rails by asking, “OK, so aside from doing the hard things first (or last), what tools are you guys using to increase your output/productivity? I only have one – Google Keep.”

“I use Evernote, probably for nearly the same purpose.” [Ryan]

“I used to use the pomodoro technique, and used a timer.” [Eileen] She explained, “It’s where you work in short intervals with breaks! So 25 minutes of work with a 5 minute break, for example. TomatoTimer is a flexible and easy to use online Pomodoro Technique Timer. It enables you to really focus in on something then give your brain a break.”

“I use google sheets a lot, but that’s mostly prospect management,” said Dan. “I do what I call ‘clean sweep’ start of every month, where I compile all notes into set of to-dos, sheets, etc.”

“Todoist.” [Sherad]

“I use the clear to do list app on my phone obsessively.” [Dan]

“I use a non-ruled Moleskin for all notes/meeting notes/brainstorms and then weekly and monthly reviewing and scanning to Evernote relevant pages.” [David]

There was general consensus that disposing with lines, and turning back to trust a pen and blank sheet of paper are still the fastest way to put thought down.

“For a time,” Dan offered, “I was interested in the nifty slate tech, where it’s like a clip board, you doodle or take notes and it goes into the computer etc, or using say a live scribe pen for big meetings and really capturing good notes… the art of note taking is a lost art in today’s society.”

Wil went fishing for answers to a different question: “What do you do at the END of the day to be more productive? Like looking back on your work, checking stuff off, etc? I don’t do anything,” he admitted, “but should.”

“Definitely planning out tomorrow and beyond, and a quick review of the day,” said Ryan, “But that usually happens an hour or two after work ‘ended’.”

“Reviewing my to-do list, seeing what I finished and didn’t, planning ahead…” [Eileen]

“I personally like to clean and make sure everything is organized at the end of each day.” [Sherad]

“Yeah, crossing things off! woohoo!” said Dan. “And cleaning the desk for next day, that’s important for me.”

“What are the main benefits you’ve found from having an end-of-day routine?” asked David.

“I find it makes the next day much easier for me. A quicker start,” answered Eileen.

Ryan replied, “It keeps me clear on purpose – particularly on days that were full of distractions – gives me a time to make sure that I’m refocused on what matters and not just chasing tasks.”

You have to love when Founders truly open up in the company of other Founders – and when they can still make room in impossible schedules for things like the following…

“I know this one is probably corny,” Wil began, “but I always end my day with every last thing I can think of that I’m thankful for. Like down to how good my lunch was. What I find is that it centers me toward things that are awesome/positive. It also helps me sleep better.”

On another note, Dan cautioned, “Dangers in this tho is that we fool ourselves into thinking making the list is doing the list.”

The importance of journaling as a way of getting things down before they’re swept aside in overworked brains came up, before Wil asked, “So what are you guys using for team productivity?”

“Asana for kitty, devs and team love, I love it.” [Dan]

“I’m still stuck on spreadsheets,” said Wil. “I use a single spreadsheet that lists all the departments we have (marketing, design, dev, etc) and then what the top 3 tasks are each week. It’s super simple but super effective. I like to have a simple view that shows week-over-week progress on our work globally.”

“I’ve got a colleague that is running teams around the world using Trello and Slack,” said David.

“In addition to spreadsheets,” Dan declared, “I love a good war room as well – immerse yourself and the team in the concept and madness, the audacity of invention.”

“Is this a physical war room?” David questioned. “I’m of the same mindset.”

“Yep, physical war room, padded walls, skylights so you can see clouds moving, and you’re in there like CSI looking at the murdered victims pics, with classic string connecting things, and then someone’s insane sketch of the future in the corner where someone who slept there and had a dream for how the product should work in 2048 – deep down I always wanted to be in advertising.”

Eileen joined in, “The growth team at startups is half remote, so we have our war room online every weds! It’s great to just hear what everyone’s up to and get rid of any road blocks.”

“Anyone use Align (from Gazelle’s)?” David asked. “It’s a tool for aligning teams around your annual, quarterly and weekly priorities and goals.” Ryan noted its similarity to LiquidPlanner used by for consulting. “It’s from Verne Harnish, founder of Gazelle’s and writer of Scaling Up and The Rockefeller Habits.”

Wil wondered, “Has anything you guys have implemented had a major impact? Slack has changed our biz for sure.”

Ryan said, “I’ve found that there was as much value in the implementation of productivity / tracking tools as actually using them. They force you to review your processes in detail and question how you are working, not just what you are working on.”

productivity hacks


“There we go… since were talking productivity,” said Dan.

“That sorta goes to my point earlier of getting good at what NOT to do,” noted Wil

“We need the alexa note taker app,” ventured Dan. “I want to say ‘alexa, take notes for the following meeting, current believe level 40%’ and alexa takes notes, recording and auto inserts things like ‘yeah sure’ or ‘as if’ every other line of note taking.”

“Not sure Alexa is there yet,” Ryan said. “I asked her to play Bruno Mars yesterday and she played Barney Children’s songs.”

Dan was not dissuaded. “alexa or audible computing, which is really just the ‘computer’ from the original star trek will be doing so much more over the next 24 months, really. Sure, we’re all chasing the holy grail of AI tech, but audible computing is where consumers will convert next.” He later added, “ai and bots are gonna be our best form of true KPI performance; we’re all gonna be managing a herd of bots one day.”

“Is there anyone who ever had or currently has a virtual assistant?” asked Devon Milkovich.

Wil answered, “I don’t but some of my friends who run fairly good sized businesses (I’m thinking Andrew Warner at Mixergy) uses a VA as core backbone to automate their processes.”

“I used a trio of them from the Philippines for an events-listing website for simple data aggregation and content, and it worked swimmingly,” said David.

“I know that they’re becoming more common, especially as people are looking to improve productivity — aka focus on the big tasks not necessarily the tedious ones. We have Zirtual at Startups and sometimes multiple people from one company would utilize the same assistant,” Devon said.

“Zirtual needs that human API, woooo there we go,” Dan grew inspired. “Simulated authenticity… bring it! I need to try out the good VA – I need a good VA for my insanity – ya know the VA for wellness and resilience is likely next. I think that’s on the rise too, like VA that helps you cope. It’s really not that crazy, Japan has rent a virtual or in person boy/friend girlfriend, the app was a hilarious experiment that took off…”

“People need help doing work, yes, but today’s society needs VA’s to just cope as well.”

“One of our Zirtual people has a client that calls just to catch up sometimes,” said Devon. “It’s not too far fetched to having a coping VA.”

“We’re in this magical time,” Dan continued, “where we can propose slight correlations on what could be based on the tech and infrastructure available, and then just sell the lifestyle of it, and if market is large enough, % conversion and boom, biz…”

“Anyone @here suffering from major productivity issues that they want to talk through with the group?” Ryan asked

“I’d like to get my staff more productive but they just hang out and chat with Founders all day,” lamented Wil.

Ryan was quick to point out that things could be worse, they could be out catching Pokemon.

“I think the hardest thing is knowing that not every hour is productive .. we tend to find some good hacks to break up our days/weeks.”

“…(like the work from home wednesdays), and I think that’s gone a long way,” said Wil. “I think realizing that you only have a small window of true productivity and trying to optimize for that really matters. ‘I only have 5 productive hours per week .. problem is I don’t know which 5 they are.’”

“We’ve talked about this a lot,” Ryan pounced, “one thing we didn’t really talk about was trying to hack the periods that are productive – and duplicate them. Possible? Once you recognize your productive periods – can you reverse engineer them and attempt to build more?

“I have sort of an If/Then formula brewing, that combines my boundaries/expectations with the availability of the right next-level leaders and plan,” David replied.

productivity hacks


Dan left a parting doodle. Time had run out, with that marvelous question left hanging in the air. Consider it a gauntlet thrown down. Who has the answer, the solution that can deliver… personalized maximum productivity?

About the Author

Keith Liles

Keith Liles is a freelance writer who loves travel, music, wine, hiking, poetry, and just about everything. He practices saying “yes” to life vigorously, rehearsing for the phone call when he’s asked to tour with Bruce Springsteen and the E Street Band. Follow Keith on Twitter @KPLiles.

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