Highrise — Three Years Later…

Three years ago today, Basecamp announced Highrise was spinning off as our own company. We knew we had a good tool on our hands that was already well loved by tens of thousands of users (some of whom are celebrating 10 year anniversaries every day!). So we had to make sure any changes we made simplified people’s work or gave them powerful new tools instead of ruin their current workflows.

We took great effort to roll changes out gradually. But over time you can see how far we’ve come:

Three years ago vs Today

icons defined below from top to bottom and left to right across the image… icons not part of Highrise, though emojis definitely are available 🙂

🐷 — Latest activity filters so you can get to what matters to you quickly whether it’s notes, emails, files or team stats.

🐶 — Good Morning (or Evening), our Group Inbox, so whether it’s your incoming leads, your existing customers or even incoming job candidates, you can collaborate as a team to address, assign, and prioritize inquiries as needed.

🐱 — So much on contact filters… a whole new UI:

Three years ago vs Today

Your ability to filter down to the exact data you need is so much more powerful with everything from combining field filters with tags, to NOT tags and Company tags, to new view filters that allow you to find contacts without tags or notes or emails in a certain period of time… and more.

🐭 — Recurring tasks remind you to follow up with your most important customers on a regular basis.

🐹 — Deal custom fields, filtering and exports allow you to track and report on the data you need at a whole new level.

🐰 — Broadcast is simple bulk email so you can stay top of mind with your leads and customers whether through drip campaigns, newsletters, or onboarding emails without the hassle of another complex tool.

🦊 — Recency search allows you to return results based on recency rather than relevancy when you’re looking for that note from the other day.

🐨 — Filters allow you to drill down to a contacts activity and find information quickly.

🐻 — Auto populated avatars so you can spend time following up instead of updating everyone’s profile.

🐯 — Threaded comments so you can tell who said what when about whom. But also what it was related to :).

🐼 — Email integrations with Gmail and Outlook so you can send email directly from Highrise without having to go back and forth between apps.

🐮 — Predefined values on custom fields so your team won’t end up with twelve different variations of ‘Active’.

🦁 — Additional settings like our Slack integration so you can work more efficiently between Slack and Highrise, email templates that allow you to store common messages for reuse, and a referral program where you can give AND get credit for sharing Highrise.

In the last year alone we launched a brand new Android app, iOS 3.0 (rewritten from scratch), reporting and stats, autoforwarding for everyone, and even the ability to turn off features your team doesn’t use.

And all that work has not been in vain:

The content for the FrontRunners quadrant is derived from actual end-user reviews and ratings as well as vendor-supplied and publicly available product and company information that gets applied against a documented methodology. The results neither represent the views of, nor constitute an endorsement by, Gartner or any of its affiliates.

Awesome CRM for a small business on a budget, or a start up like mine. Highly recommended to those who just need simple, easy-to-use, intuitive CRM. — Thomas Lyon

So easy and intuative! I use it with my network marketing company and it helps me keep my tasks in order as well as remind me what and why my customers purchased before. — Kari Larned

Perfect CRM for our business. We can’t imagine our business without it! — Chris Sands

Our organization relies greatly on Highrise, this CRM is superior to many we have tried in the past. There are so many great customizations that allow it to work perfectly for our business. It is very clear that the development team here is very active and always rolling out amazing and useful new features. Absolutely ecstatic about our choice to be organizing our customer relationships with Highrise. — Trevor Howard

But what we’re most proud of is that even with all our improvement Highrise is even closer to our vision of the Simplest CRM. Our customers can focus on what matters, rather than learning and mastering another tool or trying to figure out a useless piece of eye candy and what it means.

We’re proud that Highrise allows our customers to connect and build relationships with their leads and customers. Because business should be about people NOT tools.

Want to know more? Read about how Ken Jansen uses Highrise for his real estate business.

View at Medium.com

Check it out for yourself. Sign up for a Free 30 day trial.

Spread the word

Photo by lee Scott on Unsplash

Recently a young actress had an audition for an important role. Problem was, she was up against ‘a far better actress’ competing for the part.

Most of us find ourselves in that position. We want a chance. There’s just someone better.

Back in early 2013 when I was still testing early versions of my writing software, Draft, a user emailed to tell me he lost his writing.

Ugh. My system for auto-saving your writing still had a lot of trouble in non-perfect situations: older browsers, flakey internet connections, computer sleep, etc. He wasn’t happy, but was understanding as I helped rescue what I could.

Today, through a lot of work and code, Draft’s autosave system is (knock on wood) much more bullet proof.

But there have been many similar examples of that situation I was in. I had created writing software. It wasn’t the best writing software. But I was getting people to use it.


I had realized from years of creating businesses that most people work years building mediocre things, sometimes finally building something great, then trying (and often failing) to tell a lot of people about it.

When, they should have started with the end.

In 2011 when I was coming off a failed project at Y Combinator, I vowed to write at least one thing a week, sharing ideas, things I observed, my succcess and more often my mistakes. And my followers grew.

So, when I had early versions of Draft, they were the first people I’d tell, and occasionaly disappoint. But eventually, when Draft was ready for primetime, they were the ones who helped spread the word.

“It was between me and another girl who is a far better actress than I am, far better, but I had the followers, so I got the job.”

A group of followers she gained while we watched her play Sansa Stark in Game of Thrones.

Now, I’m no Sophie Turner. But if it’s so important for even a star like Sophie to build an audience to help propel her career, imagine how important it is for me.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.

Highrise 3.0 for iOS

For an app that’s been around since 2007, two iterations of its iOS app seems a bit on the light side. We agree. So today we have not just one announcement, but two:

Highrise 3.0 for the iPhone is now available to everyone.

It has the basics from before. Stay up to date on your team’s activity. Easily search your leads and quickly call, text, or get directions. Plan your day with tasks and follow-ups.

And it has some important new features.

Search leads by tag. View tags on contacts. See upcoming tasks when viewing a lead.

Scroll through all of your tasks. Whether you have 2 or thousands of overdue or upcoming tasks… though we still can’t help you get them done. 🙂

And more… like the ability to enter custom fields and choose from predefined values, dial incorrectly formatted international phone numbers, emoji, saved recent searches.

Alas, it doesn’t have everything for everyone yet. Some will notice it doesn’t have Cases or Deals.

But, our second announcement is that this is a whole rewrite of our mobile platform using C# and Microsoft’s Xamarin. This allows us to:

  1. update more frequently
  2. add functionality easily
  3. update it in parallel with our Android app. For those of you using the Android app from January, we have the same features headed your way soon!

So we can get Deals and Cases added a lot easier now. Please stay tuned if that’s something you need. And if you want to hear more about our choice to use C# and Microsoft’s tools in our mobile development, here’s an interview with Michael Dwan our CTO.

Here’s some feedback so far:

Just Right (iankennedy) August 7, 2017 The perfect CRM for a small business with multiple offices. We use Highrise to coordinate several offices and hundreds of clients. The mobile app is great for entering quick notes or adding new contacts on the fly when out in the field. Take [conversation] out of email and put them in Highrise

If you enjoy it, we’d greatly appreciate a review on the App Store, and if you have any issues or feedback, there’s a Help & Feedback button in the app to send us your info.

Download Highrise 3.0 for the iPhone.


In 1952, the Boston Symphony Orchestra put up a screen during musician auditions to make them “blind”. They had been hiring more men than women and were trying to figure out if they were biased in their hiring. Still, the audition results skewed towards men. Why?

There’s a bar my wife and I like to visit near San Francisco’s Fisherman’s Wharf called The Buena Vista. They serve a delicious Irish Coffee. Even more memorable is Larry Nolan one of their frequent bartenders. If you go there during the week, sit at the bar. You might get a special chance to see Larry perform magic while you enjoy your coffee.

A few weeks ago my wife, three year old, and I travelled to the Bay Area. My sister-in-law just had surgery and we went to help with chores and recovery. Things like driving the kids to school, taking her to appointments, etc. We spent a lot of time visiting their neighborhood and local spots, so didn’t even make it into San Francisco to visit our favorite bar.

So it was a nice surprise to see a Buena Vista at the airport on our way back home. It wasn’t the same atmosphere of course, but at least we could get a tiny taste of our favorite San Francisco-esque thing.

When our waitress came by though, she looked grumpy we were there. Immediately I thought she wouldn’t be a very good waitress. We asked if they had chocolate milk, our 3 year olds favorite drink. She answered curtly with a flat, “No.” She wasn’t any friendlier while we placed the rest of the order. Great. Not only we do we not get to see Larry, but this waitress is terrible.

Minutes later the waitress came back with our Irish Coffees. But she had another drink. A giant bottle of Chocolate Milk. She said she went next door to the adjacent store because she remembered they sold chocolate milk.

What an incredible move. Blew me away. Very few people would go to that length to make their customers happy. My daughter was thrilled.

Maybe our waitress was just having a bad day. Or maybe that’s just how she is — not a lot of smiles or cheery conversation. But I took all those reads and turned them into an assumption that she was a poor waitress and didn’t care about serving us.

I couldn’t have been more wrong.

Of course men aren’t better musicians than women. So what was going on at these auditions?

The Boston Symphony Orchestra kept exploring how to make their auditions more blind. They asked musicians to take off their shoes before walking across the stage to their audition spot.

Bingo. The sound of the musicians shoes were giving away their gender. Audition results went to almost 50/50 men/women.

I had a chance to catch up with a friend of mine last week, Kurt Mackey. Today he runs Fly.io. At his previous company he instituted blind interviews. The system allowed for interview screening questions that involved code, but hid details about who the interviewees were. And the results were fantastic.

But it’s not just hiring. Bias and poor assumptions creep into everything we do. Look how wrong I was about something as trivial as ordering food at a restaurant. The whole experience humbled me in my ability to read people and showed me how poor some of my knee jerk assumptions are. It’s a huge reminder how much work we need to do to rid ourselves of biases.

I left that waitress a big tip.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.

Daniel Craig— Flip flopper

In celebrity news this week, Daniel Craig will be back as 007 in the next James Bond film slated to be in theaters Nov 8, 2019. (My birthday by the way. Thanks MGM)

But his return is quite the surprise for us interested in the movie franchise. When Time Out asked Daniel about returning for the next Bond movie after Specter in 2015, Daniel let us know:

I’d rather break this glass and slash my wrists.

Daniel Craig is a giant flip flopper…

As many families do, after a long week, my wife and I don’t feel like cooking on Friday night, so we look to eat out. We are terrible however with the decision about where to go.

We simply don’t care enough. I’m not a picky eater. I don’t feel strongly about most restaurants we can choose. We hem and haw about going to this place or that place. I remember nights where we would eventually just give up on our plan to go out, since we couldn’t decide.

Then we had a kid, Addison. She’s three. Most of you know at least something about three year olds. Holy hell they have strong opinions.

Think getting her to wash her hands before dinner is going to be easy tonight? Forget it. She’d rather throw herself from the stairs.

But this has also been a blessing. For those dinners on Friday nights when we have trouble deciding, we just let her decide. And she does. Instantly.

Her strong opinions lead to very quick and certain action. And we keep tapping into that.

For many parents, choosing a preschool is a stressful activity. It wasn’t for us. Folks are amused when they ask us “How’d you choose Addison’s preschool?”

I tell them, “Addison picked it.”

She’s three!? And she picked her school when she was two?

Yes. My wife and I had been debating between three different preschools. They all had various pros and cons. In our minds they all felt a bit equal. We didn’t feel strongly. The decision started dragging on.

So we just let the strong opinion holder decide. And she did. It took seconds. She picked the school she wanted and we went with it. It’s been a great choice. Of course if she said, “I want to go to school at McDonald’s” we’d have intervened.

“Strong opinions, weakly held” is a phrase a bunch of interesting people have publicly adopted: Marc Andreessen, Fred Wilson, Jeff Atwood.

Paul Saffo, a technology forecaster, and once the Director of the Institute for the Future, coined the phrase in the 1980s that leaders who want to successfully lead their organizations through uncertainty and ambiguity need to have “strong opinions, weakly held”. It’s the only way to get anything done.

Should we build this product? Prioritize that feature? This marketing plan? If you have weak opinions you won’t have the energy to get unstuck. You’ll be paralyzed in indecision. And you won’t be able to convince anyone else to follow you through the challenges.

But having a strong opinion doesn’t mean you shouldn’t be open minded. Be passionate about your ideas and thoughts. Use that energy to get the evidence to back them up and get people to help you. But don’t close off arguments. Flip flop when something convinces you you’re wrong.

One thing that caught my eye about Daniel Craig is how productive he’s been, especially now since Spectre the last Bond movie he had announced would be his last in 2015.

4 projects quickly followed in 2017 with major changes to his normal character repertoire and a TV show with a demanding schedule.

Compare that to the last two Bond actors who were in just a couple projects in the two years following their roles as Bond.

Pierce Brosnan and Timothy Dalton after their last Bond movies

Daniel Craig’s strong opinions appear to have given him the ability to make quick and decisive action to tackle some really interesting and different projects in 2017.

But he has flip flopped.

That’s fine. The rumor was an enormous paycheck convinced him, but that’s been debunked. I think he simply likes the role. And much needed rest after the crazy production of the last Bond movie gave him a new perspective. He was always open minded about the opportunity, even if his opinion was once strongly against it.

I think more of us have to step up and form strong opinions about the decisions we have. Anytime you have a inkling about what’s right, use that energy to see it through. Stay open minded when people and situations naturally push back, but either way you win and increase your productivity, energy and drive.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.

Dear Blue Apron,

This is one of those open letters of advice. It’s from a friend, me. And it’s free advice. So it might be worth just that — nothing.

But I, and probably everyone else, noticed Amazon encroaching on your business. And since I’m a big fan, and we at Highrise have weathered some intense competition too, I thought some of our learnings might trigger something for you.

Also, you and I both understand, I know absolutely nothing about your business or running a public company. I hate those open letters that are like “YOU NEED TO DO THIS”. You don’t. I suspect you’ll be fine if you just stay true to yourselves.

So even if this doesn’t help you, maybe it’ll help someone else.

Know Thyself

When I took over as CEO of Highrise in 2014 — which was also the same week I signed up for Blue Apron! :) — I really had no idea what I had on my hands. I didn’t create Highrise. I didn’t know why 37signals/Basecamp bothered to build it. I didn’t know who its best customers were.

So we did a bunch of customer interviews getting to the real Job people hire Highrise to perform. Despite our headlines and website copy we found it wasn’t a group address book or a contact management tool. Customers were buying the fastest, simplest thing they could get up and running instantly to track leads and manage follow-ups. That’s extremely specific. But knowing that fuels a ton of decisions now. From marketing site changes, feature prioritization, and most importantly communicating to the world what we do.

If you were to interview me about Blue Apron you’d hear: I first signed up 3 years ago. It was a crazy time in my life. I had a three month old, and had just started a brand new job as CEO of Highrise that very week. Jason, the CEO of Basecamp, our parent company, introduced it to me.

He too was about to be a dad. Interesting connection. 🙂

I had zero time to worry about meal planning. We were ordering delivery and takeout way too much and feeling the effects. We needed help. Jason mentioned Blue Apron sends you everything to make a great and healthy meal. Perfect.

One wrinkle was that meals still felt like they were taking too much time. But I embraced it. What I thought was convenience I was looking for, became instead a way to retreat some from work and the craziness around me.

I could just cook and think about something else.

Eventually, however, the long cooking sessions won out and I took a break. Shortly thereafter you introduced the Family plan and I came right on back.

The Family plan was the perfect fit. We just have a family of 3. Our now 3 year old daughter is finicky. So two meals a week for 4 people most often turns into 4 dinners with the leftovers warmed up the other two nights. And it seemed like you got the message on time because more recent recipes take less time to make.

Somewhere in there is a path that might not be what you expected. Or want to take. But it might be a path only you can tackle better than Amazon.

Convenience or Luxury?

One of my favorite books in the world is Trade Off by Kevin Maney. Kevin explores how successful companies appear to either fully embrace High Convenience or High Fidelity. Fidelity being things like luxury goods or experiential products. A good example of convenience vs. fidelity are MP3s vs. concerts.

Companies that try to be both high fidelity and high convenience fail at both, and fail at attracting customers for the long term.

From our customer interviews, I know Highrise is a high convenience business. People come to us because they need a solution as fast as possible. If they have to get on a phone call with a sales rep to go through pricing options and possible customizations we will fall on our face.

I feel like there’s room here for Blue Apron to choose to either go for higher fidelity or higher convenience.

On one hand you’re nailing convenience, but I’m sure there’s more you could do to remove steps from your service like even faster recipes.

But fidelity might be a better choice. Amazon after all seems to always gun for high convenience. Maybe the farm to table work you’re doing is already the best way to combat their push to convenience.

Out-teach Amazon

We can all probably predict that Amazon isn’t going to get into the business of teaching me to be a better chef. But I really could use the help.

I have always hoped to master some principles of what makes a great recipe. I want to feel confident going into someone’s pantry and inventing a recipe with optimized ratios of salt, sweet, acid, umami, etc.

But I’m not confident. I’ve cooked so many meals already in my life and I feel like I’ve learned very little. It could be an interesting area to take Kathy Sierra’s advice to out-teach your competition. The process of cooking Blue Apron meals could become more of a learning experience on how these recipes come together if that was a path you chose.

Anyways, good luck. I’ve really enjoyed being a Blue Apron customer over these years, and think you’ll be able to keep competing well even with the likes of Amazon in the ring. I’m even about to make your Corn and Cheddar Enchiladas as soon as I’m done writing this letter 🙂

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.

Not meeting your goals

I gave up daily vlogging recently. On January 1, 2017, I announced I’d start uploading a video every single day. There was no end in mind. Some people have taken on this challenge and lasted days. Some people have lasted years. I lasted a little over 3 months.

The breaking point was a company meetup at Highrise, a simple CRM company I took over from Basecamp in 2014. Our meetup was just a handful of days. But those days were optimized to spend every minute possible together since we’re all working remotely the rest of the year.

There was a lot of great footage from the meetup, but I didn’t have any time to edit fun stories together. Or think about pacing. Add music.

I shot YouTube live videos to at least get something out and keep my commitment to the daily vlog, but my YouTube stats started to tank.

So, I decided to focus on creating better videos — ones I thought could get the most likes and views — for each and every upload. My daily vlog became a barely weekly vlog. Sometimes I’d get two videos done in a week. Sometimes none.

And I started disliking the project more and more.

On the first day of my Sophomore year in high school, there was a “welcome students” event in our auditorium. I was barely paying attention but heard my name called out. Ugh, what’s this about? The dread became surprise and then elation when they announced I had the highest grade point average so far of our entire class of 400+ kids. Woah. I was not expecting that.

With this newfound ability to compete at having the highest grade point average, I just wanted to keep competing. Could I be my high school valedictorian in a few years?

That Sophomore year, I was in an AP (Advanced Placement) art class. For some reason the teachers and I did not get along. And I guess I didn’t have much talent with the art assignments. It showed in my grade for the class. My hopes for valedictorian were evaporating. It felt awful.

Junior year rolled around, and work just got harder. More tough classes, even less time for school work with all the extracurricular activities I was doing. My goal of having the best grades got worse.

My stress got worse.

But then I started making better friends with this guy, Al Wyman. Al and I had known each other since basketball camp in grade school. When we found ourselves in the same ethics class Junior year, we began talking more and more.

Those talks changed something in me. We’d banter back and forth about the books we were reading (or supposed to be reading for class) from the likes of Herman Hesse or Camus. And I realized how much I enjoyed our chats about “school work”. Not the competition for grades. But the act of learning, debate, application.

Why was I so focused on grades, when I should be more focused on the act of education?

In that ethics class, there was a project about the famous Edward Hopper painting Nighthawks: Redraw the painting and write an essay of whose in our version and why.

I experimented with the idea that maybe I could just focus on learning and enjoying the experience instead of getting the best grade.

But there was a catch. There wasn’t enough time to thoroughly tackle this project without pulling yet another all nighter. So I just didn’t do it when the teacher wanted it done.

After the project was due, I finally had an opportunity to focus on getting the project done and give it my all, learning even more about the original painting, and about the people I felt interesting enough to belong in my version. I turned the project in a couple days later and felt great about what I had learned and produced.

What happened was kind of a surprise. The teacher took it, looking at me a bit quizzically. I said, “Sorry I couldn’t turn this in on time. But here is my work. I hope I can still get some credit for it.”

A few days later he gave it back to me, with a great grade on it — even accounting for the points he took off for turning it in late.

It taught me a valuable lesson. I could still “perform well” without actually focusing on that as a goal. Really, I needed to take care of myself, and commit to a system of learning, not a goal of the best grades.

My time in highschool got so much better after that. There were multiple projects I started turning in late so I could get more sleep. And I learned so much more in the process.

I still ended up with a really high average when I graduated. I wasn’t the valedictorian. I was close, but it didn’t matter anymore. That last year and a half of high school was some of the best time of my life, and I got so much out of it.

If I look back at my career, the best moments are when I repeated what I did in high school — focus on systems, not goals. If I focused too much on where my startup would be when I wanted it to be there, I was miserable. When I focused on just showing up, learning as much as I could, delivering things our customers wanted on a regular basis, I enjoyed it, and we still got great results.

My first Y Combinator startup from 2006 didn’t turn into the mega-success I had envisioned, but became an enjoyable ride that still propelled my career forward and turned into even better and brighter things for others as well.

I had a goal with Y Combinator in 2011 to create a Groupon-sized success. Again I became miserable. Until I instead focused on a system of creating things that met needs I understood well because I had them myself.

That led to Draft, simple writing and version control software. It wasn’t the thing I envisioned making in 2011, but the system got me what I’d call a pretty wild success.

Now I run Highrise. The founders of Basecamp handed me the reigns when they wanted to spin it off. That was never a “goal”. How could it be? No one could have made it an intention. But this system of showing up every day and creating new things regularly got me here.

Staring at my YouTube stats was a mistake. There’s so much to getting traction, and so much of it isn’t under my control.

What I can focus on is showing up every day. Filming. Editing (when I can). Getting on camera. Trying to find a story from the day even if it doesn’t work out.

So I started daily vlogging again.

I sure as hell enjoy it more. And I think I might still get great results. Maybe not what I envisioned at first. But it seems like things have a way of working themselves out.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise.

You Won’t Get Rid Of Your Problems. Best You Can Do Is Trade Up


I used to have this business partner Jim. He’d drive me nuts. Our startup business was part of the second class ever of Y Combinator during the winter of 2006. We built a virtual stock exchange that businesses could use to improve their forecasts. This was the early days of Ruby on Rails in 2006. Back then, Rails apps required a lot of care and feeding — they crashed, a lot — with our increased load.

Jim would wake me up after just a few hours sleep, “Nate, the site’s down again.” Requiring me to scramble. The growth of our app just gave us more problems. I was frustrated, exhausted and stressed. Jim’s attempt at comfort was, “These are good problems to have.” Thanks for nothing, Jim.

Growing up, we didn’t have a ton of money, creating all sorts of problems I wished to eradicate later on in life. One example that’s going to be tough to forget — in college on a car ride back home, I rolled up to a gas station while running on fumes. I pumped the tank full. Walked into the gas station to pay and found my ATM balance was $0 and credit cards maxed. I was soaked in sweat as I asked my passenger if she had some money to lend me. Luckily, she was already planning on giving me gas money for the trip.

It’s stuff like this that I couldn’t wait to get rid of as I got older. College would lead to a great paying job, and I’d move past these problems, and live a life far from this stress. But I got it all wrong.

My 3 year old has a cold again. She coughed all night. Sleep sucked. My head hurts. I have a cold now too. My day also entails trying to figure out why our search engine traffic to Highrise has been sucking. I’m frustrated.

But with the little bit of wisdom that comes with age, I realize more and more that my youthful desire to eradicate all the problems in my life was pointless. There’s always going to be a new problem I need to deal with. The sick kid. Her 3-year-old tantrums. The challenges growing a business already well ahead.

And worrying about search engine traffic is far from the frustration I felt in that gas station 20 years ago. The problems I had running a startup trying to gain just a tiny bit of traction in 2006 was so much worse compared to running a business today with tens of thousands of happy paying customers today.

Jim wasn’t wrong at all. We can’t eradicate our problems. Best we can try to do is trade up.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise.

“I think I’m having a heart attack”

In 2011, I was part of the Summer class of Y Combinator, working on a startup creating online games, and I was stuck on a problem.

I hadn’t slept well for days. Weeks. I stayed up as long as I could keep my eyelids open each night, powering through work with tons of caffeine. I NEEDED TO FIGURE THIS OUT.

One night, as my hands started to shake, and my heart pounded in my chest, I called my wife and told her:

“I think I’m having a heart attack.”

We’ve all been in situations where we needed to come up with solutions to tough problems. Probably more times than you want to remember. And, I bet, all that thinking sometimes led to some headaches and stress.

But did it lead to a good decision?

In 2009, 4 researchers, Loran Nordgren (Northwestern University) and Ap Dijksterhuis, Maarten Bos, and Rick van Baaren (Radboud University Nijmegen), wanted to find out.

So they gave study participants a decision to make: which car is the best quality (as determined by outside judges) given a set of criteria to read. One group of participants was given simple criteria to determine the quality of those cars, while the other group of participants was given more complex information.

Then, each of those groups of participants were either given time to think consciously about their decision on which cars were higher quality or the participants were distracted by a game so they didn’t have conscious thought available to spend thinking about these cars.

Of the participants who only had to come up with car quality decisions based on simple criteria, they all did well, whether you had to think consciously about it or you were distracted. No big surprise.

But, for the complex car decision, this is where it got interesting.

The people, who spent conscious time just thinking about their decision on which car was the highest quality, only got the decision right 20% of the time. That’s much worse than a coin flip. But of the folks who were distracted by something else, they were right about 60% of the time.

This was just a lab result though. Does it work in the real world?

The researchers came up with another experiment. This time, they went through a bunch of products from a store like IKEA. They had a set of separate judges rank 40 products from simple to complex purchases. Then these researchers went and surveyed people who bought these products. The survey asked participants how much time they thought about making their purchases beforehand. Was it a lot of conscious thought or unconscious?

For complex purchases, it was the people who spent less time thinking about the purchase beforehand who were happier with their purchases weeks later.

Now, this isn’t some black and white strategy. But it sure does lend evidence that “sleep on it” before having to make a complicated decision sounds like pretty good advice.

A few weeks ago, we moved our backend provider for how we store files in Highrise.

It wasn’t going that well.

This is some stuff that’s been running for years. Changing it introduced all sorts of problems in corners of our application that hadn’t been explored in a while. There was plenty of planning and procedures to back out of trouble. But still, on a Thursday morning at 3AM, Michael Dwan, our CTO, and I found ourselves putting out fires.

I was a wreck the next day. Completely useless. I should have just taken the day off.

But… I’ve learned my lesson.

I got to bed early on Thursday. Friday I took the whole afternoon off to just hang out with my kid and my mom. We went to the zoo. Had lunch. It was fantastic and I felt recharged.

Five years ago, when I called my wife about my impending heart attack, I had already been powering through weeks of sleep deprivation with Red Bull and coffee, despite the constant advice from partners at Y Combinator to take care of ourselves. But that night, I decided to try a shot of 5 hour energy just to top things off.

Thank god I was eventually able to calm my breathing and heart rate. Hopefully I haven’t caused myself permanent damage. It’s a lesson that sticks with me deeply today. What was I thinking? That was freaking scary.

For what? What was it all worth? For my startup to succeed? That software I was working on isn’t even around anymore.

And I never did come up with a solution to the thing I was struggling with the most during those caffeinated benders. Maybe I could have, if I had just gotten plenty of sleep.

P.S. You should follow me on YouTube: here, where I share more about how we run our business, do product design, market ourselves, and just get through life. Also if you’ve enjoyed this article, please help it spread by clicking the below.

And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise.

New in Highrise: iOS Beta is ready, Outlook.com integration, and more…

It’s summer here at Highrise headquarters, but that doesn’t mean we haven’t been busy. We’ve got exciting stuff to announce today…

iOS updates — Beta testing

We’ve been working on updates and new features to our iOS app. Today we’re announcing a public beta. If you’d like a chance to test it out, you can do so here. We expect to officially release it very soon. And don’t worry Android users. The same updates will come to you soon too.

Outlook integration

Highrise has always supported any email system with the use of a ‘dropbox address’. You can BCC your Highrise dropbox address when sending an email to file it in Highrise. And if you click on an email address in Highrise, your default email service will open with your dropbox address automatically BCC’d. You can also forward or auto-forward incoming messages using the same address, so you can get both outgoing and incoming email easily into Highrise.

But we’re always looking for how we can save steps for our users.

Today we are thrilled to announce an integration with Microsoft Outlook, which allows you to send email directly from Highrise when you connect a Microsoft Office 365 or Outlook.com mailbox to your Highrise account.

Read more about the new Highrise Outlook integration here.

Better Excel imports and error messages

We recently announced some changes on better import messaging. And today we have more time saving tweaks to improve that important step of getting your leads and contacts into Highrise.

You’ve always been able to import from Excel to Highrise. But one quirk is that we didn’t support the more modern .xlsx file extension. The workaround was “easy”. You had to save your file from Excel to the older .xls standard (or .csv).

But what a pain. If you missed that we didn’t support .xlsx and tried to do an import, you’d get an error, then have to go through the process to get it converted.

Just too many steps…

Read more about better imports here.

Easier avatars

A couple changes that will greatly simplify using avatars in Highrise:

Highrise has always offered some help adding avatars to new contacts when based on email address or Twitter handle. But you didn’t have much choice on what we used. That’s all been greatly improved and simplified…

Read more about avatar improvements here.

If you’re a Highrise user, I hope you enjoy those. Please let us know if you ever need anything — Highrise related or not. We’d love to help.

And if you aren’t a Highrise user, now’s the time! 🙂 If you need a no-hassle system to track leads and manage follow-ups you should try Highrise.

You should also follow my YouTube channel, where I share more about how we run our business, do product design, market ourselves, and just get through life.