The Challenge of Rolling Solo

Being a solo founder is hard.

It’s almost trite to say, but I’m in it and it’s real.

I’m not sure if it’s just the fact that I’m a solo founder or the solo person employee.

Even though I’ve started 3 companies before and had my fair share of success and failure, I’m still struggling with anxiety and fear and this damn feature that I was supposed to ship 2 weeks ago and that is still sitting in my task list, 20% done.

Humans are social creatures, and I am human.

It’s hard being alone.

Do I need a co-founder? Or maybe just another person? These are the issues I’m wrestling with right now.

Once upon a time, I thought money would solve all this stuff. That the struggle was only for people who didn’t have money. I didn’t really believe it, but the tohught would buzz around my head, a bias––almost like racism––that I didn’t consciously acknowledge or believe to be true, but that was there in my heart.

Now I have money and I’m still in the struggle. Funny how life works.

I’m lucky though. And privileged. And stoked about what I’m doing.

But still, I was supposed to this damn feature 12 days ago and it’s still just 20% done. Something isn’t working.

Maybe I’m being too hard on myself. Maybe this is all just normal and I need to power through.  Or maybe I just need another human being to work with.

I had an intern living with me over the summer, sleeping in my garage. He was awesome and I had a blast! He was young and had a lot to learn, but he had the work ethic and mindset of a founder. Effing brilliant too. It was so much fun working with him! He felt like a younger brother. Smarter than me in some ways, less experienced in others.

Funny enough, my best work relationships feel that way: like siblings of different ages, each with our own strengths and weaknesses.

I made Mourtallah an offer for after he graduates in December. He accepted. His start date is 6 weeks away. 

But in the meantime, I’m struggling. Feeling in a rut. I hate that feeling.

I want to be going at warp speed again. I need to be going at warp speed again.

But maybe that’s not always possible when you’re human.

Does this ever happen to you? How do you deal with these slow downs in productivity?

P.S. Talking through it like this really helps. Maybe that’s step one?

Thanksgiving Letter to My Portfolio CEOs

Matt Mireles
From: Matt Mireles
Date: Fri, Nov 23rd, 2018 at 9:56 AM
Subject: Thankful
To: Founders


Hi Folks,
On this Thanksgiving holiday, I am thankful for… you.
You are my tribe.
A lot of you are the people I talk to most and have become some of my closest friends.
Most people don’t get to work with people they admire so deeply. Most people don’t get to be as real with the people they work with. Most people do not get to be part of work that is so important.
I feel very lucky and privileged to be a part of your lives, and to have you a part of mine.
And for this, I am very, very thankful.
Happy Thanksgiving to you. I hope it’s an awesome one!

Moral Courage: Not Taught at Harvard

  Harvard doesn’t teach moral courage. It can’t––at least not without breaking its model. No university can. Like anything else you might want to learn, to master moral courage, you have to practice doing it, and universities have no mechanism for this. A university can teach you to master reading or writing or even discounted cash-flow analysis. You’ll read some theory, maybe get a lecture, then be forced to do lots and lots of practice. And it’s through practice that you will develop mastery. When a university like Harvard claims to “teach” moral courage, what they really mean is that they tell students about the subject without forcing or even giving them an opportunity to practice it. Imagine if Harvard offered a lecture-only course on how to read, then claimed they actually taught reading. They would be laughed at. When Harvard Business Schools says they teach students moral courage and that, as my friend Michelle claims, that moral courage is *central* to the curriculum, it is only at this most superficial, shallow level of teaching. Traditional schools––Harvard is not alone––are unable to teach moral courage in a meaningful way. They might talk about it and expose it’s existence to them, but they don’t actually teach it to students Teaching requires practice, and schools have no good mechanism for this. They could change this. They should change this. But I’m afraid they probably see it as out-of-scope for their institution. To teach moral courage to the elite, now that would be a radical change.

Alone on Thanksgiving? Come to My House.

Do you not have Thanksgiving Plans? New in town? Are you wondering WTF you are going to do on Thursday? Feeling broke / lonely  ?

If so, you should come to my house and join my family for Thanksgiving. We’re making smoked Turkey and yams and stuffing and all sorts of other deliciousness. Our house is in downtown Menlo Park 5min from the Caltrain and a few blocks from Stanford University.

Truth is that no one gets anywhere in this world alone. When I was 20, it was the people who picked me up on my cycling/hitchhiking mis-adventure down the California coast and let me stay in their homes on Xmas. When I was 25, it was the New Yorkers who welcomed me into a new city and taught me how to stay safe in my job as a paramedic. When I was 29, it was the entrepreneurs & investors who introduced me to Silicon Valley and showed me how to go from Zero to 1.

And now, I feel compelled to return these favors however I can.

So…if you’re in San Francisco Bay Area and you need a place to call home for Thanksgiving, let me know. We saved you a seat at the table.


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Alone on Thanksgiving? Come to My House.

Do you not have Thanksgiving Plans? New in town? Are you wondering WTF you are going to do tonight? Feeling broke and maybe just a little lonely?

If so, you should come to my house and join my family for Thanksgiving. My girlfriend Stephanie is making Turkey Dinner. We have beer, wine and not much in the way of family around these parts. We live in downtown Menlo Park 5min from the Caltrain.

Feel free to bring a friend. We’ve done this a few times before and it’s always a lot of fun.

RSVP using the form below and if you’re bringing food, please indicate what kind & how much in the Google Sheet that this form redirects you to after you hit submit. Once I get your RSVP, I’ll send you my address and other details. Dinner starts ~5pm and will go until ~9pm

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Getting Unstuck

“The only difference between Elite Entrepreneurs and those just getting started is the amount of time we stay stuck.”
Dan Martell

Winning is all that matters. You only have to get to the top of the mountain once. How much time you spent falling down at the bottom beforehand doesn’t matter (other than the opportunity cost, I suppose.)

Q: How long did it take for Steve Jobs to get back on the horse after Apple fired him?

A: More than a few minutes. Also, who the fuck cares?!?

Being able to get yourself out of a rut is a good thing. But even the best of us end up there sometime.

Something to think about.

Letter to a Fired Founder

A friend of mine just got fired from his startup. As a founder, he was classy, loyal and relentless. He behaved like a champion. But despite all this, he got shitcanned nonetheless. So I wrote him a letter:


I know you must be feeling pretty shitty right now. Probably a little bitter too. I know I would.

[!Name], I’ve seen you in action. You’re an inspiring leader. You’re a motherfucking relentless hustler. And you’ve got the heart of a lion.

If you go off and start a company some day, I’d be honored to work for you. Or co-found. Or invest. Or whatever.

In the coming weeks, I’d advise taking some time off, investing in your mental health and getting out of the valley. This is what I wish I had done.

Travel. Mentor. See the world outside of Northern California.

It’s not a marathon, it’s a fucking ironman.

And whenever or wherever you need me, I’ll be here for you. I am your friend.

Thanks for being part of my life and supporting me so much over the last few years. I hope that now I’ll have the chance to be there for you in your time of need, whatever that looks like.


-Matt Mireles

Be there for your friends, the real ones. Tell them what you see in them. They deserve it.

No One Is Self-Made

One of Robert Putnam's famous scissor graphs

Fatherhood has changed me.

In my pre-fatherhood twenties, I thought of myself as a self-made man. I viewed the world through an individualistic, narcissistic lens and my accomplishments, I believed, were largely my own. I had taken risks and busted my ass to get whatever I got. I congratulated myself and began — quietly — to scorn those who had failed to put themselves in the right industry, the right career. They were weak, I was strong, and that’s the game.

Fatherhood has taught me that no one is self-made.

My son will never remember how much he has been given. He will never remember the love he got at three in the morning when his tummy ached from constipation pains. But it — along with the thousands upon thousands of other gestures of love — will teach him to feel safe and secure in his person, which in turn will fuel his confidence and one day (I hope) enable him to take economic and social risks that propel forward his civic, social and business life.

Matt Reading to Luca

I am constantly impressed by how much my son depends upon me, upon us, for guidance. If we don’t teach him to eat with a fork, he will not eat with a fork. If we don’t teach him to be kind, he will not be kind. If we don’t teach him to read, he will not read. It takes effort, consistent effort, to raise the man we hope that he will become.

Civilization is not an automatic process.

Stephanie and I read to him regularly. When I stop, Luca cries. He will take this for granted as a natural part of life, because it is all he knows. Yet it will give him a permanent leg up in life, especially compared to his peers whose parents are not so involved, maybe because they’re too busy trying to make ends meet or maybe because they simply don’t know that it matters.

So too will the $20,000+ / year (!!!) we’re investing in his education at the Palo Alto daycare (in SF, the pricetag was $30k) pay off in ways large and small. His best friend is the child of two Harvard graduates. He and his little girlfriend have so much fun together. Amidst all that fun and play, they talk and teach each other things. The effect of peer influence is real. He learns from her. I see it. For a 3 year old, his language skills are quite advanced, yet she talks even more than he. His growth accelerates when they are together. And so too does his advantage.

My boy is not above hitting, kicking or biting. He is a child. I am the disciplinarian in the family (shocking though it may be to my elder siblings). He needs guidance — sometimes stern, sometimes soft. But he needs his parents, both his mom and his dad. Daddy in particular doesn’t fuck around. Resistance is futile, as I like to say. He knows that.

In those moments when I’m dragging him to the naughty corner (a pain for us both), I often wonder what would happen if I wasn’t around or if I didn’t care. What if Luca didn’t have a dad who was around? How would he turn out? It’s easy to imagine a different life, one without the discipline, without the guidance, without daddy to enforce lessons of right from wrong.

Same with Stephanie. Whereas my favorite past-times with the boy are reading and wrestling, hers are talking, more talking and playing with him & his toys (something I find dreadfully boring). Were it not for Stephanie, he’d be physical brute with middling verbal skills.

Together, we give him what he needs. Or so we endeavor.

Were it not for both of our efforts, our incomes and our social capital, where would he be? How could he hope to compete with the children with the children who are so priveleged?

Such are the thoughts that have been occupying my mind as I read Our Kids — The American Dream in Crisis by Robert Putnam. The book tells the story of an America increasingly divided — not by race or ethnicity — but by class and educational attainment.

Over the last 40 years, college-educated, rich Americans have clustered together, enjoying all manner of positive network effects much like the ones I just described. Americans without college degrees are living together too, suffering from the same sort of network effects, except in reverse: crime, drug use, low expectations and bad schools.

The graph below and other “scissor graphs” like it tell the story.

One of Robert Putnam's famous scissor graphs


They all look ominously similar. Each graph shows two lines diverging over the past several decades in the experiences of American kids at the top and bottom: in the share born to single mothers, in the chances that they’ll eat family dinners, in the time parents spend reading to them, in the money families invest in their clubs and lessons.

“Every summer camp you went to or every piano lesson you got or every time you went to soccer club, you were getting some advantage,” Putnam says, “that somebody else out there — Mary Sue — was not.”

from The Terrible Loneliness of Growing Up Poor in Robert Putnam’s America

This other America is not foreign to me.

Before I was a father, before I was an entrepreneur, I worked as a 911 paramedic in the Harlem and the Bronx. Monday through Thursday from 2005 to 2008, I attended Columbia University, taking courses in international politics at the best political science department in world. But come 7am on Friday, I put on the uniform and got to work on 12 X-ray (central Harlem) or 17 Willy (South Bronx). The people we served were poor. We were mostly tourists in their lives, parachuting into their living rooms or street corners to fix an asthma attack or an overdose.

In my time, I took care of a woman who’d had 30 abortions. I saw the police gleefully electrocute a man just because he made some noise in his jail cell. I did CPR on a floppy baby whose father had accidentally smothered the child in his sleep.

Now that I’m a father, I think often of all the sons and daughters growing up in that other America. It was a very different America from the one that my son will know.

How will these kids in that other America fare in a future where software has eaten the world?

Given the competitive nature of the education system and the job market, what chances for advancement will they have? How is it right and just that the circumstances of my son’s birth will determine so much of his future?

Their prospects look grim.

This is not the America that I want.

This is not the legacy that I want to leave behind.

This is not the American Dream.

I’m not sure what the answer is or how I can be a part of it, but as an entrepreneur sitting in the heart of Silicon Valley, I’m actively looking to be part of the solution.

If you know anyone who’s working on this problem, please send them my way. I’d love to be a soldier in this struggle.

A Christmas Gift for My Dad

My dad looking happy with his new computer setup

How I Created the Perfect Computer Setup for My Nearly Blind, 85 Year Old Father.

After 85 years on this earth, my dad’s vision has declined dramatically due to macular degeneration. It got so bad that he was using a magnifying glass to read emails on his 27-inch iMac. This is especially tough because my dad is actually in the late stages of writing & publishing a 600+ page book about Billy the Kid, the famous outlaw.

As a Christmas present, I replaced my dad’s iMac with a Mac Mini and a 50-inch TV. Now he can read emails and browse the web with just his regular glasses on. He’s happy as a clam and I’m really happy for him.

How It Started

My dad had been using a late-2009 iMac passed down by my older brother. He would bring it with him when he’d visit us in San Francisco. This is what it looked like setup at my standing desk in the old living room:

Here's my dad two years ago using his old computer at my standing desk. Pretty clever. He hacked my standing desk using a chair and an ottoman.
Here’s my dad two years ago using his old computer at my standing desk. He hacked my standing desk into a sitting desk using a chair and an ottoman. Pretty clever.

My dad would bring his 27-inch iMac on the plane as checked luggage. He reinforced the original packaging with plywood to make the box travel worthy.

Dad at the airport with his gigantic portable computer
Dad at the airport with his 27-inch iMac in tow. He reinforced the original box with plywood to make it impact-proof and wrapped it in plastic to make it waterproof. Then he tied it all together with an old telephone cord.

Everything was great, or so I thought, until I visited my parents’ home this Christmas. Dad’s vision had worsened and he was struggling to see the letters on the screen. To read emails, he would pick up a magnifying glass, hold it close to his eye and push his head toward the screen.

“Papa,” I said, “there’s got to a better way!”

The Perfect Computer Setup for My Nearly-Blind, Elderly Father

Late in one afternoon, I took elderly parents to the Apple Store. After briefly considering the new 27-inch iMac, we picked up an upgraded Apple Mac Mini for $700, though you can buy the base model from Amazon for $459. I chose the Mac Mini because:

  • Just a computer – Works with any size computer monitor.
  • HDMI port – can use a TV instead of a traditional computer monitor.
  • Small size – easy to transport on a plane to San Francisco or car to the Apple Store.
  • Apple Genius Bar – my dad can take it in to get fixed and troubleshoot any problems that crop up. <––Makes life way easier for me and my brother!

Next stop: Fry’s Electronics of Anaheim, computer store of my youth. In case you’ve never been, Fry’s is an electronics chain known for low prices, massive warehouses and used-car-esque salesmen.

I walked into Fry’s thinking we’d buy a ~32-inch computer monitor for $500, which seemed like a decent option. However, I was concerned that we could get something much cheaper online, but then I realized: We could actually get my dad a big ass TV and use it as a monitor!

Me, I couldn’t deal with having a TV as a monitor. The resolution just isn’t high enough. I need a higher density of information and pixels. My dad however had the opposite problem. He didn’t just need a big screen, he needed big pixels and big text. The bigger, the better.

Dad at Fry's checking out TVs.
Dad at Fry’s checking out TVs. He’s still a bit confused about the end goal at this point. 

After perusing a few smaller options, we settled on a 50-Inch Flat Screen Television with 1080p resolution for $425 (refurbished). If you’re willing to settle for something slightly smaller, this 40-Inch, 1080p TV from Amazon looks like a great deal at $279.

I chose the big screen TV because it is:

  • Bigger display size than a regular monitor.
  • Cheaper than a regular monitor.
  • Text appears bigger than a regular monitor.

This turned out to be an excellent decision financially and practically. There’s no way we could have gotten a display that size for anything close to that price.

Since my dad already had a keyboard and mouse that he liked, we just needed an HDMI cable and a webcam to use for grandpa-grandson FaceTime.

Mom and Dad FaceTime with me and grandson
Mom and Dad on FaceTime. Me and Luca say hi.

FaceTime with my parents is one of my favorite evening pastimes with my son, so having a functional, low-hassle webcam attached to the computer was crucial.

We chose this HD Webcam by CreativeLive!. We paid $40 at Fry’s, but you can buy it Amazon for $20. Things I liked about it include:

  • Works reliably with Mac / Apple products.
  • 720p HD resolution.
  • Built-in microphone.
  • Lots of positive reviews.

Getting everything in the car paid for and in the car was a bit of a pain in the ass, but we made it home safe just two hours after we left. Getting started was pretty easy because I’d already set my dad up with a Dropbox account and used that store all his important files, including his book. I also made sure that he shared all his folders with me and my brother, so that we could poke around with files just in case he got into trouble.

A Huge Win for Accessibility & Usability

I was pretty sure my dad would be happy with the end result, though he was a bit skeptical during the purchasing process. After a day at the helm of his new computer, he was unequivocally happy with the new setup. “It’s tremendous!” he said, calling me the next day. “Son, I can read everything just fine. I don’t need the magnifying glass.”

My dad's new computer setup - rear view
This is me showing my dad how to share a Dropbox Link. Man, that’s some huge text. 

My dad's new computer setup - side view
Suddenly, my dad could see the text and do work without squinting or using the magnifying glass. Pretty awesome!

My dad looking happy with his new computer setup
My dad with his new computer setup. “It’s tremendous!” he told me the next day. “I can see everything with just my glasses.”

In case you’re interested in buying this setup for someone you love, I created an Amazon store so that you can buy this setup for someone you love who is vision impaired. 


Farewell to All That

“Each time you crest the rise in front of you, it just makes it clear the size of the even larger hill that looms beyond it. It goes on for a long time.” -Marc Randolph, Founder/CEO Netflix


After six years in the saddle as an entrepreneur, I’ve decided to hang up my hat and get a job.

Two weeks ago, the first wire hit our bank account––EasyFridge‘s first investment! I was excited at first. It felt good, validating and all that. After a few days, however, a different thought occupied me: “Am I ready to do this for the next five years?” 

 If you’ve never started a company before, this is a question you need to ask yourself.

For me, the answer was “definitely not.”

I’m tired. I took just two weeks off after the SpeakerText acquisition closed. In retrospect, that was a mistake. I should have taken more time, have made an honest effort to charge my batteries. But I didn’t. And now I’m paying the price.

As a result, I decided to return the capital to our investors (100 cents on the dollar) and move on.

Now I’m looking for a job.