Social Support

A few weeks ago my father was taken by ambulance to the emergency room with trouble breathing. After that 5 day hospital stay, he’s been doing really well!

But one thing that stands out from the experience was how my own psychology fluctuated. During the initial couple days I’d go to sleep at my parents by myself leaving my mom and father at the hospital. And I was a mess.

Plunging ourselves into ice cold water isn’t usually a pleasant experience. So it’s a common practice research psychologists make people do when studying how people deal with pain. They call it the cold pressor test.

And in 2003, a group of researchers performed the cold pressor test, but this time they tested what would happen if people with their hands submerged in ice cold water were with someone else. A friend. Even a stranger.

The people who had company during that painful moment felt less pain.

Things remarkably changed when everyone descended upon the hospital to join my mom, father and me. My sister came into town with her boyfriend and my niece. My sister’s best friend showed up for multiple visits and help. My wife grabbed my daughter and all our pets and moved them over to my parents place. Even a great friend of mine came and spent a couple hours visiting my father and eating some McDonalds in his hospital room for dinner with us.

Despite all the upsetting and scary things we were now dealing with, it felt like a huge weight had been lifted off me when all these people showed up.

It just goes to show you how important it is that no matter what you’re going through. If it’s work or career stuff, or these moments in our personal lives, it’s important to experience them socially. Don’t isolate yourself.

Over and over again, we find that, whether we’re social butterflies or we’re introverted or we’re shy, when we have people around us, even strangers, we can far better endure the inevitable stress that comes with life.

You should follow me on YouTube: where I share more about how we run our business and just get through life.


A few weeks ago, I took my daughter to the Art Institute here in Chicago. She’s three.

So as you can imagine it wasn’t a tremendous success of actually seeing a ton of art. We had a lot of fun though doing crafts they had set up for kids and eating lunch.

My proudest moment was when she yelled out “I really like that picture!” It was Vincent van Gogh’s The Bedroom. It’s my favorite too.

There’s an interesting exercise you can do at the Art Institute or other major art museums. Go find some Picassos and note how old he was when he made them. Now find some Cézannes and do the same.

It’s possible you spot something like Economics Professor at the University of Chicago, David Galenson did.

Picasso’s most valuable work, based on prices paid at auction, peaked when he was 25.

Cézanne at 65.

Some artists peak young. Others get better over time.

Galenson saw this over and over with writers and artists in all sorts of different time periods and industries.

I think the world puts too much focus on the Picassos and the young phenoms. We overlook the Cézannes. The folks who took a while to experiment on getting better and better and who never stopped.

The thing I take from this is that if you find yourself still experimenting in life. If you don’t have it all figured out. If you’re 30, 40, 50, 60 and still don’t know what you want to be when you grow up…

There’s still plenty of room and time to get better. Your peak is still ahead.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

“Are you extroverted?”

I upload a new video every single day to YouTube about business and just getting through life. A vlog as some call it. So also, every day, I walk around talking to a camera lens in the middle of a street or crowded event.

It’s weird. It’s weird for a lot of people. So I get asked a lot: “How are you comfortable doing this?” “Do you have a history of doing something like this” But the umbrella question that I think most people are trying to ask is:

“Are you extroverted? Is that why you can pull this off and I can’t?”

The fact is, I’m probably one of the most introverted people you’ll meet. Some would maybe even label me fairly anti-social. 🙂

I really like one-on-one interactions and meeting new people. I love true friends. But I don’t like going to parties. You won’t see me at many conferences. If I am there, you’ll find me in the back row of something or closest to the exit so I can bolt.

And no, I’m not comfortable doing this. Even in front of a camera in a room by myself, I get nervous. Even though I know I have all this power to edit and redo. The first video I uploaded to my vlog was a Live video I recorded on Facebook but made it Private to just me 🙂 And I filmed it 13 times.

And I hate that attention on me as I walk around talking to a camera.

But I do it anyway.

Do I have some kind of inflated image of myself? Hard for me to judge I guess since I don’t know the self talk in other people’s heads, but I’m pretty hard on myself both in what I do and how I look.

I don’t even want to open up that therapist session on all the ways I hate how I look on camera. But some obvious ones. My complexion is terrible. Skin is oily. Now I’ve developed this recurring terrible allergic reaction that comes on when I even glance at a pine/Christmas tree and recurs randomly otherwise.

Kendall Jenner, one of the younger of the Kardashian clan, was at the Golden Globes, and it was crazy how many people called her out for the visible Acne she had on the red carpet.

What were people expecting? That she’d skip the red carpet? Stay home?

This is a huge thing that keeps people back. Vanity that they have to look perfect.

And that’s why the Kardashians are so successful. They have zero fear of putting themselves out there for every single person on the planet to see, flaws and all. It doesn’t matter what the public thinks of their skin or anything else they say or do. They aren’t afraid to embarrass themselves when most everyone else is.

People also commonly ask me if I’ve had a lot of practice doing this.

Not really. I have had some brief on-camera training as part of acting lessons I’ve taken over the years, and a big reason I took those classes was to get over my fear of performing in front of people and cameras. And that practice has helped some.

But there’s been plenty of videos, especially the live ones, where I’m sweating the possibility of saying something stupid or why on earth is my hair sticking out like that today.

So, if you’re holding back from doing something like a vlog because you’re afraid of what you look like, or you’re uncomfortable in front of a camera? I’m there with you.

But I refuse to let those things keep me back. It takes some practice. It’s still uncomfortable. It gets less uncomfortable… sometimes. And it’s worth it.

To be nobody but yourself in a world which is doing its best day and night to make you like everybody else means to fight the hardest battle which any human being can fight and never stop fighting. ― E.E. Cummings

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

How do you fire someone well?

I don’t think a “best way” to fire someone exists — but here’s a stab at trying to do it with dignity, grace, and respect.

I fired someone last year.

Ugh. It was gut-wrenching. I’ve fired people before — but it doesn’t matter how many times you do it, it always feels downright terrible.

To prepare for the difficult conversation, I asked a few mentors for advice. I also posed the question to The Watercooler in Know Your Team, our community of leaders from all over the world, to learn how others handle letting someone go.

From almost 1,000 CEOs, managers, and executives, I compiled six recommendations on how to handle firing someone with dignity, grace and respect that I thought I’d share with you here:

Privacy, please.

Choose a conference room that’s away from the team, ideally that’s close to the exits. Or, if you’re a remote team, make sure you’re in a place that’s private when you make your Skype or Google Hangout call. Make sure your phone is turned off and door is closed so you’re not interrupted. And never ever do it in a public place, like a coffee shop.

The “optimal” time doesn’t exist.

Everyone has different opinions about whether you should let someone go on Friday end-of-day, or earlier in the week — but really, it’s moot. Once the decision has been made, it’s best to let the person go as fast as possible. There never is an “optimal” time to fire someone. Don’t let time or day or day of week become an excuse to delay. The longer you wait, the more your interactions with that person become disingenuous and uncomfortable in the days and hours leading up to you telling them they’re being let go.

Cut to the chase.

Don’t dawdle or make small talk. Your opening sentence should be delivered in 5 seconds or less. For example, one Watercooler member suggested you say, “Claire, I’m letting you go effective immediately.” Be clear, succinct, and direct. Nothing you can say will soften the blow so don’t try to sugar coat your message or ask about how a project is going, etc.

It’s a decision, not a conversation.

Don’t get drawn into an extensive conversation or argument — it’s a decision that’s been made, not something that’s up for debate. Make that clear. One Watercooler member suggested that after stating that you’re letting this person go, your second sentence should articulate terms (severance, impact to equity, etc), and your third sentence should indicate this is non-negotiable. Listen to their reaction, answer questions as you see fit, but try not to get pulled into defending your decision for hours on end.

This sucks for you, but sucks way worse for them.

Another Watercooler member cautioned that you may be tempted to offer comfort by saying something like, “This is a difficult decision” or “I really don’t want to do this.” But the last thing you want to do is indulge and pontificate on how you’re personally feeling. To be frank, the other person doesn’t care how difficult the decision was for you — you made it, regardless. And, if you really didn’t want to do it, you wouldn’t have. Of course it sucks for you, but that’s not for you to impose on the person you’re firing. Find someone else to confide your pain in, and keep in mind that the decision you’re making is on behalf of the team, the company, and their best interest.

Communicate the decision to your team with grace.

Ask how the person being let go prefers to break the news to the team. Their preference might be to send a farewell note themselves, or personally tell the team members they are closest with. Other times, they’ll ask you to simply relay the news for them. If it’s the latter, share the news with respect and mindfulness. Even if the person was fired for performance reasons that were 100% their own fault, thoughtfully consider what is appropriate to disclose. Imagine if the person fired were to overhear you sharing the news with the team: Would they feel it was fair? Use this as a benchmark for how to communicate the decision to your team.

No matter how you do it, letting someone go is one of the hardest things to do as a leader. There truly is no “best way” — but hopefully these tips will be helpful should you face this situation in the future.

I know it’s helped me.

P.S.: This was originally published on the Know Your Team Blog. If you enjoyed this piece, please feel free to share + give it 👏 so others can find it too. Thanks 😊(And you can always say hi at @clairejlew.)

Hate your job? Happier times are within your grasp

As is common this time of year, I took some time to reflect on life and work. And a few different things reminded me of how incredibly fortunate and happy I am to be working at Basecamp.

But I bet you can guess the punchline — yeah, it wasn’t always like this. The year before I landed at Basecamp, things were pretty rough and I was miserable at work.

I know this feeling isn’t unique. In fact you might be feeling today how I did years ago — coming home from work tired, uninspired, unhappy, and even angry. It’s not a good look.

But change is within your grasp. It won’t be easy, but you can be damn sure it’ll be worth it. I speak from personal experience.

When I eventually reached my job-hate breaking point, the first order of business was to quit said job. I have to admit it was kind of exciting and liberating. But it was also intensely scary.

I was walking away from a good job working at a stable, respected company — a company where I could’ve had a prosperous (albeit miserable) career. I voluntarily went from having a very generous salary to one of literally $0.

Oh and by the way, as I took on this adventure of rebuilding my career I still had some huge responsibilities back at home: namely my twin infant sons and all the adulting required to keep them happy and healthy.

So you can imagine the unsettling feeling of self doubt I felt early on. More than once I wondered, “Did I make a huge mistake??”

But ultimately I realized what scared me the most was the long-term prospects of doing nothing — not just being unhappy for one year, but allowing that misery to fester over three, five or even ten years.

We spend an inordinate amount of our life at work — somewhere between 20–30% of our waking hours. How could I standby and let all those hours be filled with misery, only to bring that misery home with me every day to my family? No, if I was going to spend that much of my life doing something, those hours better be happy ones.

So I pushed aside that doubt, put my head down and got to work. I joined The Starter League and got my brain and attitude in the right space. I was learning tons and meeting great people. I felt professionally energized and excited for the first time in a long time.

I finished up my classes there and soon after I mustered up all my courage and took a long shot: I reached out to Jason Fried to ask if there was anything I could help with. We got to talking, and a few months later he invited me to join 37signals.

What an unbelievable turn of events. Going from the the worst job I’d ever had to working at my dream company wasn’t anything I’d ever expected. Fast forward 4+ years and I’m doing the best work of my career and I’ve never been happier at a job.

Now look, I’m not recounting this story as some kind of humble brag or to make myself look like hot shit. Anybody who knows me I am the furthest thing from hot shit. I’m ice cold shit.

I bring it up because I hope it shows the kinds of crazy, unexpected, wonderful things that can happen to anyone’s career if you take a chance.

I’m not special — all I did was acknowledge my unhappiness, embrace the uneasiness of change, and got to work. Yes, there was some luck involved, but even if I landed somewhere other than Basecamp, I still would’ve been happier and better off for having tried.

Of course it’s really important to remember that everyone’s situation is different, so don’t take my story as gospel.

I was fortunate to be in a position to take a chance like I did. I had years of work experience to help me recognize when to get out of an ugly situation. We were financially secure — it was a moderate risk, but I never put ourselves in any kind of precarious lose-it-all situation. And most importantly I had wonderful, incredibly supportive people around me — family, friends, teachers, colleagues, and so many others. I recognize not everyone gets the deck stacked in their favor like this.

It’s also worth noting that life wasn’t all roses and sunshine afterwards either. It took a long while to get everything back up to speed — to rebuild our finances, to re-establish my career direction, and even smooth out our family life and routine.

But in the end was it worth it? Absolutely, positively, hell yes.

If you hate your job, I’d really encourage you to consider taking action. But first you’ll need to evaluate your career situation, then decide what’s best for you and your family, now and in the future. It’s natural (and healthy) to feel scared, worried, and hesitant. Take your time, consider deeply, and take action when it’s right for you.

But no matter what your situation is, if you’re in a rough patch in your career I hope that my story gives you a spark of hope, something you can hang onto — the belief that better times await you when you’re ready.

There’s something great out there for you and your career. You absolutely deserve the happiness it can bring — go on and get it. 🤜🤛

If you enjoyed this post, please do hit the 👏 button. Thanks!


My 3 year old daughter is in school. Most of her classmates are older than her. She keeps up great. But she reported to us recently, that many kids have called her small. And it makes her feel bad.

It’s easy to just chalk this up to kids being naive. “Hey kid, comparing your age to someone whose older or taller and feeling bad you aren’t as big as them is dumb.”

But adults are just as guilty.

In a study at Harvard, researchers asked participants if they’d rather have $50,000 in a society where everyone else made $25,000. Or $100,000 where everyone else made $200,000. The prices of all material goods were the same in both scenarios. More than half chose the world where they were only making $50,000. Even if they could have more money and wealth in absolute terms, many would rather just make more than their neighbors.

I get it. I look at my career as an entrepreneur and I’d love to be achieving more. I have many colleagues and friends who’ve accomplished quite a bit more so far. And it’s easy to come away from that analysis with emotions probably not that much unlike my daughter.

The best thing for me is to make sure I spend more time comparing myself to myself. Have I grown? Am I better than I was a few year ago? Did I accomplish the things younger me set out to do for myself?

That’s who I need to be bigger than.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

“Build an audience? Bah. I’m a nobody.”

Photo by NeONBRAND

“We all know we need to build an audience. Out-teach the competition. Collect those fans and emails before I even have something to sell, so when I do have something to sell, the money will come rolling in. Enough already. I haven’t accomplished anything. No one cares what I have to say. I can’t build an audience with this track record. And I’m a terrible teacher.”

I was a broke college student. I didn’t spend much besides getting the essentials, but money made during the summer, even working as much overtime as my boss would allow, evaporated quickly. The quintessential example of how broke I was — I rolled up to a gas station on my way to an interview for an internship, pumped the car full of gas, and went inside the station to get cash from the ATM.

Except there was no cash. My bank account was empty.

I was ashamed and embarrassed going back to my car asking to borrow money from my passenger. Thankfully she was already planning on giving me gas money for driving her to her own job interview.

I was eager for any job I could find that would alleviate my situation.

So when I realized I could become a teaching assistant (TA) even as an undergrad during my senior year, I jumped on it immediately. Free education. And a small monetary stipend.

Now, traditional TAs at a place like a huge University are mostly there to help augment a professor’s lectures and curriculum. Students usually go to a lecture 2–3 times a week and meet with a TA to get some homework help and take quizzes.

Imagine my fear then when they asked me to be a TA in this experimental program where I’d be these kids only teacher. There wouldn’t be a professor or lecture. They’d come to me 4 days a week and I’d be their only source of teaching chemistry.

I wasn’t a bad chemistry student. I was after all a chemical engineering major. But I was by no means the best chemistry student I knew. And I had zero experience teaching anyone anything. And these weren’t kids. They were freshmen and sophomores. They were me just a few years ago.

How was I possibly going to teach them anything?

There’s really not some long conflict here. I just started.

I picked up their assigned chemistry book, which was similar to the one I had when I took the course, and went through the chapters just like they would. I’d work out the problems on the weekends and see how well I understood the concepts myself, and then 4 days a week I’d get up to the blackboard and try to show them what I had just learned.

I wasn’t great. But I wasn’t awful. I helped some kids through the course who themselves didn’t think they could get through it. Received some decent reviews from the students. Was even invited back to teach the same course again the next semester.

But what this whole thing impressed on me was how valuable being a teacher is, even one who isn’t all that experienced and is struggling to teach at the same time. Of course, I’m not belittling how awesome the teachers are who have insane amounts of experience. My life has been incredibly touched by them. But we shouldn’t be intimidated by them so that we don’t even bother to start teaching ourselves.

We might not be the successes we have pictured in our heads, but that doesn’t matter to the person who’s trying to get past an obstacle we just recently got through. It doesn’t matter how young you are, there’s always someone younger who wishes they were exactly where you are with something, or someone older who’s just going through their learnings in a different order.

Building an audience and teaching your potential customers something isn’t the only path to running a business, but it sure is a good one. And, it isn’t as out of reach as you probably think.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.


How do you know when it’s time to quit?

We all know people all over the spectrum. Someone who’s been working on something forever that’s never going to work out. And someone who quits every project they start before giving it a fair chance. Then we have those friends who seem to have the magical instinct to know when to quit and when to stick with it until it takes off.

So how do you know when to quit? 3 months? A year? Is there some signal to look for?

Here’s something that’s been nagging the crap out of me. I can’t get an article published in Entrepreneur. I’ve tried. Three times. More than that actually since I’ve re-pitched articles working from the editor’s feedback.

The editor just doesn’t like my stuff. No amount of traction from previous work moves his opinion.

But I’d love to continue growing my audience and Entrepreneur seems like such a great fit.

Do I give up?

Most of us have a lot of goals inside our head.

For me I want that article in Entrepreneur. I want more subscribers on my YouTube channel. I want to grow Highrise. I want to be my own boss. I want to spend as much time as humanly possibly with my family.

All these goals are a jumble inside our own heads. But the goals aren’t all of equal importance. And that’s the first problem we have before deciding to quit something.

Angela Duckworth offers a framework to help sort through your goals, in her book Grit, that’s deceptively simple and incredibly useful.

It’s a bit like a ladder. On the bottom are the smaller goals of less importance. Bigger ones above them. One or more of the goals below often support the ones above.

The Entrepreneur article is probably way down here.

While ensuring more time with family is at the top.

Here’s the magic of the ladder. As you go up, the goals should be things that you consider harder and harder to quit.

I should make sure I spend every last drop of energy and willpower I have to ensure I have the ability to spend more time with my family.

And Highrise, is, of course, of insane importance to me. But I should consider it easier to quit than say maximizing time with family.

As you go down the ladder, you realize getting an article in Entrepreneur is one of things I should probably consider the easiest to give up.

And here’s more magic with the ladder. Not only are the lower things on the ladder easier to quit, they’re easier to replace.

There are tons of small goals to replace that damn article in Entrepreneur. I could change my focus to getting published in Inc. Or spend more time on YouTube videos.

The middle goals are harder and harder to replace but they’re still replaceable. There’s nothing to replace more time with my family.

So when you start asking about when it’s time to quit something, hopefully you’ve done this exercise and at least figured out that jumble of goals in your head. This thing you’re trying to quit, is it of low importance serving the needs of the actual higher goal? Is it then easy to replace to move focus to higher rungs in the ladder?

It’s not a magic formula for which projects to quit after trying hard for 6 months, etc.

But it sure is the right place to start.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

Getting Attention

I had a vague inkling of an idea for a company in 2005. A friend of mine mentioned this new program called Y Combinator that was investing in teams willing to move to Silicon Valley and build out their ideas.

We were older (by a bunch) than the college/new grads they seemed to be targeting. We didn’t have any traction yet. Even the thing I wanted to build was based on algorithms in academic papers I hadn’t yet been able to make any sense of.

All we had was the idea and a rough prototype.

But we got invited to an interview to meet the partners in Boston.

I didn’t like our chances…

I’ve always loved magic. I still remember my first magic set. We lost the scarf immediately. It took us days to realize the scarf had vanished in the secret compartment it was supposed to vanish in.

Over the years I kept dabbling in magic as a hobby.

When I was in seventh or eighth grade, my father came up with the idea that I should ask my old kindergarten teacher if I could perform my magic act in front of her classroom.

I remember seeing the teacher on the playground during a recess we shared with her class.

I wussed out.

I was too embarrassed. But, telling my father I didn’t have the courage was worse than the embarrassment, so when the opportunity presented itself again, I walked up to her, and nervously asked.

She agreed. I performed a magic act in front of her class and it went over pretty well.

Fast forward to High School. I love playing basketball, but didn’t get picked for the Freshman team. So my dad told me to ask the coach if I could practice with the team in case they needed extra bodies.

I thought I was going to die walking into that coach’s office with my heart pounding this fast. The coach was nice, but said “No” to my offer. It wasn’t the answer I wanted of course.

But I didn’t die from the embarrassment.

Both examples were practice at putting myself out there and ignoring all the possible embarrassment I could be putting myself in.

When I got out of college I was a glorified secretary at Accenture (Andersen Consulting back then). They didn’t hire me to be a software engineer like I wanted because I had zero training in software engineering. I was a chemical engineer. My job was to record meeting minutes and make sure people signed documents. I hated it.

So besides the countless late nights learning to make things with software, I also started a habit of emailing random partners ideas I had. Like how convenience stores could start shipping things from store to door or that we shouldn’t have to wait in line at amusement parks or how to try on clothes online with just a camera. Just vague, naive ideas (though to my credit they do all exist today in some form).

I’d use the global email directory to find partners at the firm who might be interested. The guy who had the relationship with 7–11. The one who was in charge of the Disney account. The one who was doing projects with Gap.

What’s the worst that could happen? Maybe they’d ignore me. Maybe they’d reply that the ideas were terrible. Maybe they’d even fire me. Unlikely, but sure. The most likely result was that I’d be embarrassed.

But I’ve been embarrassing myself for years thanks to my Dad. 🙂

One of my emails was forwarded to someone already doing some R&D for retail clients like Gap and he invited me into his office. He gave me a job doing software development in his R&D group at Accenture.

How’d I get into Y Combinator? Well, I passed the interview process just like anyone else that gets into Y Combinator. They might have liked the prototype we built. They might have liked our design aesthetic.

But there’s one thing that I think helped a lot.

The night before our interview, my partner and I went to get dinner at an Indian restaurant near Harvard Square. As we were finishing up dinner, all the partners of Y Combinator walked in.

I was sweating right through my shirt when I walked up to their table as we were leaving. I introduced us and mentioned we’d be meeting them in the morning.

It was just a tiny thing. It took seconds. Didn’t measurably do anything for us. But it added a bit of attention to the partners’ minds the next day. And when those Y Combinator interviews are only 10 minutes long, you can use anything you can to help get their attention.

Want to get attention? Embarrass yourself. Ship a product people might hate or criticize you for. Introduce yourself to someone who could by all probability just ignore you. Publish something no one might read. Yes, your pride takes a hit after the rejections, but you’ll still be walking this earth. You do enough of these and those rejections start to roll off.

Do even more of them and they get people’s attention.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

How to make my company big

How do we get bigger? Get more money? Grow the team? Get bigger office space? More clients?

My three year old daughter has been literally dreaming of going to a magic show. So we went to the first one that crossed our path and seemed relatively kid-appropriate.

I regretted going immediately.

The tickets were general admission. We got there early just to wait in long line. The heat was cranked up. I had to lug around our winter gear while trying to entertain my kid as her boredom progressed.

Sitting in the theater made the regret stronger.

A larger ballroom had some of those temporary moveable walls inside to make smaller rooms. We were in a smaller room.

I’ve been doing and watching magic my whole life. I’ve seen the David Copperfield and Penn & Tellers. This wasn’t any of those.

It felt claustrophobic.

And then there was the stage. There weren’t many rows of people. We were in row 8. But there’s no way we were going to see this magician with the heads in front of me.

A woman in the next row had already pulled out binoculars.

Here’s hoping my three year old would cooperate because getting out of our seats was going to be a very public ordeal.

I had dreams of my first startup getting huge. I had created Inkling with Y Combinator back in 2006 and my vision was that everyone would want to use us to help make decisions.

It didn’t turn out that way.

It turned out that gathering the wisdom of the crowd is most valuable to people who have really big crowds. Banks. Conglomerates. One of our best customers was the US Government.

So we didn’t get the crazy amount of customers I imagined. But I knew our customers extremely well. We’d travel to visit their offices. We’d have a meetup where we’d hang out for a couple days and have intimate meals together. One customer came over to my partner’s house and we brainstormed all day together. And if I remember right, that customer slept on my partner’s couch that night.

We don’t have those same relationships with customers at Highrise. I mean, don’t get me wrong, I try. I converse at length with many customers who email me, or comment about something we’re doing on Twitter or YouTube. I’ve had talks with customers not just about work but about their families and struggles. And I’d like to have a meetup soon.

But because of the scale of people, it’s hard to concentrate the attention like we did at Inkling.

At one point early in the magic show the doors to the room opened up again for some late comers. It distracted everyone. The late comers were stuck standing near the door instead of trying to find seats worried they’d cause even more interruption.

But here’s an example of how different his show was.

The magician, Ivan Amodei, paused and asked his staff to make sure the standing room crowd got seated in empty seats he spotted on the other side of the room.

This isn’t something you’d see most magicians, or any performer really, handle gracefully in larger shows with these types of distractions.

My fear about the magic show was replaced with, “Woah, this guy is doing something different.”

He bounded through the center aisle talking with people. It didn’t matter you couldn’t see the stage great because he was constantly on a chair or in the aisle showing off things. He had all of us standing up as part of various tricks.

Then my worst fear about my daughter started. 3 year olds don’t have the same social graces as we do. She began to squirm and talk about leaving.

But she snapped out of that when Ivan came through the crowd asking everyone for loose change.

When Ivan saw my daughter holding out her fist with coins, he stopped and conversed with her about her age. She was shy and not talking and I thought he’d leave quick.

But he kept at it. Getting her to finally tell him her age. Then he started giving her some of the coins he’d already collected making sure her tiny fists were as full as he could make them.

He then mentioned her multiple times later in the show.

Even the stories behind the magic had a personal touch that included stories of his kids.

It finally dawned on me why the name of his show was “Intimate Illusions”.

Ivan wasn’t in this small room because he was still hoping to be this bigger magician. Ivan was small on purpose.

He used that small room as a tool.

I look at the fun my daughter has at three.

The freedom she has to explore and experience that she won’t have when she’s 30. And I remember the strengths we had with just a handful of customers at Inkling that are much more difficult to recreate at Highrise.

Also note, Ivan isn’t just getting started. He’s been winning awards for his performances in 1995. His current show alone has been going on for over 8 years.

He could easily sell out larger crowds. But he’d lose the feel of this show.

Ivan isn’t small because he can’t be big. He’s small because Ivan uses small and intimate as a strength.

If your business is small or just starting out, don’t let these days of small pass through your hands in your desire to get big. Just remember how much you’ll lose too.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.