Love and Tacos

In late 2015 Brittany and I made our first angel investment, and it wasn’t in a tech startup. It was in an industry where we have far far far more domain expertise. If you know us well, you know I’m talking about tacos.

You see, long before burritos became the cornerstone of my diet, tacos were my first love.

I discovered them in the summer of 1994 as a 12-year-old kid in Boyle Heights, Los Angeles at a restaurant called King Taco. That summer, my friend’s dad “hired” my friend Carlo and me to do demolition work in East LA on a construction project he was developing. I learned a lot of lessons that summer that stuck with me till this day:

  1. Treat all people with respect no matter who they are.
  2. Don’t start a job unless you plan on finishing it.
  3. Tacos are fucking incredible!!

Of course I had had tacos before King Taco. But this was the first time I’d ever been introduced to an authentic street taco. Corn tortilla, carne asada, onions, cilantro. Nothing more. I consider it a pivotal life moment.

Flash forward seventeen years to Chicago 2011. In one of life’s weird twists of fate, I manage to meet my wife Brittany while in line for tacos at a restaurant called Big and Littles. I like to claim that I won Brittany over with my vast knowledge of Mexican cuisine. This line, of course, alway elicits eye rolls from Brittany whenever I say it in public. But whatever. I’m pretty sure it’s 100% accurate.

It didn’t take long for us to fall in love after meeting in that taco shop, and about 18 months later we were married. Naturally, we served tacos at our wedding. This was Taco Pivotal Life Moment #2

Flash forward to 2015 and what I’m hoping will be Taco Pivotal Life Moment #3.

Our friends Mike and Stephanie Gaines tell us they are going to open a tacos and margaritas restaurant in SF called Glena’s.

Whaaaaaa??? Muy Interesante!!!

When Brittany and I hear the news it takes us about a half a second before we decide we to get on board with this. We had never made any angel investments but this seemed like the ideal place to start. In fact, I practically begged Mike to let us be their first investors and hitch our wagon to their star. Fortunately for us, they said yes.

We couldn’t have been more thrilled for Mike and Steph when we got an email last week saying that Glena’s was officially opening to the public.

It’s hard to put into words how excited I am about this investment and why I think it will be hugely successful, but I’ll try to explain as best as I can.

First there are the obvious reasons.

  1. It’s tacos!
  2. Mike is a Michelin star winning chef with an incredible track record.
  3. Stephanie has years of front-of-house experience and is the perfect complement to Mike.
  4. Mike and Steph are amazing human beings. They’re the kind of people you want to root for.
The Glena’s Team
How do you say product market fit in Taco?

But beyond just these obvious reasons, I couldn’t put my finger on why I was so bullish on Glena’s until the other day after a conversation I had with Joanne Wilson and Anna Barber. Joanne’s a prolific angel investor with over 100 investments and she’s often been the first money in. I asked her for advice on what has made her so successful.

“Is there a common characteristic for the successful startups you’ve invested in and if so how do you spot it before you invest?”

For Joanne, she said the common characteristic has been the startups with founders who knock down walls. The founders who don’t give up in the face of adversity. The founders who are going to keep fighting all the way to the end. Those are the ones who care. Those are the ones you want to invest in.

And that’s when it made sense for me why I was so excited about Glena’s. Over the last year-and-a-half as an investor I’ve had a front-row seat as I’ve witnessed Mike and Steph’s grit and determination through all the ups and downs that come along with starting a business.

When their first lease fell through after they were already super-deep into the process, they didn’t quit. They doubled down, hosting pop-up restaurants around town for almost a year to keep people excited before securing a new lease. When a big potential investor pulled out of the deal because timing no longer worked for him, they didn’t throw in the towel. They doubled down. They took out a loan and bet on themselves. They did the work. They pushed through. They willed their way to make it happen.

This is the EXACT attitude you see in all successful entrepreneurs.

Entrepreneurship is hard. The odds are stacked against you. Talent, luck, timing, skill, product, execution— all these things come into play in determining whether a company is successful or not. But the ones who win aren’t necessarily the people with the most talent, or the most money, or the best idea. These things are just the table stakes. The ones who win are the ones who are willing to knock down walls. The ones who are willing to bet on themselves. The ones who refuse to quit. That’s what I’ve seen in Mike and Steph, and that’s why I’m so excited for this investment.

Glena’s just opened a few days ago, and of course it’s too early to tell what will happen. But what I can say is that it’s already been a joy getting to work with Mike and Steph and if Joanne is right and grit and determination do in fact play a big role in determining success, then Glena’s is already off to a pretty incredible start and I’m going to go out on a limb and say that this is just the beginning of Taco Pivotal Life Moment #3.

Oh hey there. As a reward for getting all the way to the bottom of this Medium Post enjoy this Glena’s al pastor bonus-taco section. You are the winner!! If this doesn’t make you want to go eat at Glena’s right now, you are probably dead.

Tacos for President 2020!
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Playing Offense in the Age of Mass Incarceration

Today we live in an era where one in three black men will go to jail during their lifetime. One in three!

Crime rates have been dropping for decades. Yet, paradoxically, the prison population from 1978 to 2014 has risen 408%.

To put this in context compared to the rest of the world, we only have 5% of the world’s population, yet we have more than 20% of the world’s prison population.

Stop and think about that. That doesn’t make any sense, does it? How is that even possible?

The answer is that while the crime rate in the United States is similar to crime rates in other countries around the world, it’s the incarceration rate that differs here. We’ve made the decision to become the world’s largest jailer. Rather than attempt to lift people up, we’ve chosen to lock them up. As a result we’ve robbed generations of families the opportunity to live the American dream.

And if you’re wondering, who are these people we are locking up, it’s disproportionately black and brown people.

This in a nutshell is the system of mass incarceration, and in my opinion it is the single greatest US human rights travesty of our generation.

In late 2015 I had an opportunity to hear civil rights leader Bryan Stevenson speak on a panel with John Legend and Harry Belafonte about racial justice. Towards the end of the discussion, he asked the packed audience a series of questions.

If you lived during the age of slavery, raise your hand if you think you would have been an abolitionist?

Most people raised their hand. Then he asked:

If you lived during the Jim Crow era, how many of you would have stood up and fought against the terrorism and lynchings enacted against black people?

Again most people raised their hands.

What about the era we are living in now, the era of mass incarceration?

The room went silent.

It was stunning.

His point was well taken. The era of slavery didn’t end in 1865. It evolved. Today’s mass incarceration is yesterday’s Jim Crow. We evolved from chains to nooses to cages. The means of subjugation are different but the racial narrative has always been the same.

The question is, why are we not treating today’s system of mass incarceration the same way we would have treated Jim Crow or slavery.

In 2015 Bryan Stevenson brought me to tears and I told myself in that moment I was going to do more. In 2017 I’m starting with baby steps.

As a first step I’m committing to writing more and speaking up more when I witness injustice. The system we have is broken. But it doesn’t mean it can’t be fixed. I think the very first step is truly acknowledging it for what it is.

As a second step, I’ve made a decision to be more intentional about my charitable giving. I tend to play defense when it comes to charitable giving. When my friends ask for money to support a cause they care about, I’ll give $50 and call it day. At the end of the year I have given to all these people I care about, but I haven’t actually helped move the needle for any cause I care about.

For 2017 I’ve decided to stop playing defense and start playing offense. So this year I’m dedicating my entire giving budget to a single organization called Defy Ventures.

Defy Ventures is an entrepreneurship program for people in prison. Think of it as a Techstars or a YC except the entrepreneurs are behind bars rather than co-working spaces.

Graduation day in prions with Defy Ventures via INC

As a third step, I am planning to go to prison more. I have been a mentor with Defy since 2015 and it’s been phenomenal. But this past December I had the chance for the first time to go to prison with the organization and invite about 25 LA entrepreneurs and investors with me. I won’t share too much about the experience because I want everyone to go and experience it for themselves but it was deeply powerful. I can promise you, if you go on one of these trips, it will change you. I’ve committed to going on four more prison trips in 2017 and hope to see friends in the tech community join me in LA, SF or NY. If you’re interested in coming to prison, please get in touch.

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When Brittany and I left Chicago we had made a decision to optimize the next phase of our lives for happiness. We knew we were moving to the West Coast but we didn’t know where. We looked at Portland, San Francisco and LA and spent about 10 days in each city exploring what it would be like to live there.

Portland and SF were great (we lived in SF in 2012–2013) but ultimately we decided on LA. To be honest, I just kind of meh on the city itself when we made the decision. The biggest driver was family. I had been away from my family for the last 17 years and both of us felt it was important to be close to people we love.

But one short week into LA, I’m already starting to fall in love with this city.

The tech scene here is exploding and growing faster than anyplace else in the country. But it’s not just the tech community that is thriving. Everything in LA right now seems to be thriving: art; music; food; culture; tech.  The city is in the midst of a renaissance.

Though I won’t pretend to have figured out the freeway system yet, I’m beginning to feel more like a native. In my first week in LA, I witnessed a mudslide, took a road trip to Vegas, and ate Chinese food in the San Gabriel Valley. Also, I did 90% of this in a Prius. So yeah, I’m pretty sure this makes me a certified, full blown Angeleno.

There’s a hashtag people in the LA tech community throw around a lot: #LongLA. Before I moved here I thought it was a little goofy — you know a little too rah-rah LA. But now that I’m here I think I’m starting to get it. This place is pretty great.

When Hate Becomes Mainstream


If you’re following the news you’ve probably heard about all the hate crimes and hate speech that has proliferated since Trump became our president elect. It turns out that stuff’s real. You can add my story to the growing list.

Novemeber 7th

On November 7th, I was walking through the subway in New York when I heard someone mutter “you almost hit me with your box, you fucking n*gger.”

Let me repeat this.

I was in the subway in New York City. Not Alabama. Not Mississippi. Not South Carolina. Not Texas. Not Georgia. And it wasn’t 1865 either. It was 2016.

“Seriously?” I thought to myself.

I turned around.

Behind me was a middle aged white man in a pinstripe suit and overcoat. Before I could even stop to think, I found myself confronting him.

“What’d you say?” I asked.

“I said he almost hit me with his box”

“That’s not what you said. You said ‘you almost hit me with your box you fucking n*gger.’”

“Yeah, okay. So? That’s what he is.”

“Maybe he did almost hit you with his box but you don’t need to use the N-word.”

And with that, our conversation ended. I walked away rattled. He walked away angry, bitter, and muttering to himself.

I immediately regretted not saying something more forceful.

What I wanted to say was “FUCK YOU, you human piece of dogshit. Bigotry has no place in our society and you represent the worst of America.”

But I didn’t say any of this because I was scared. He was a belligerent bully acting erratically. I thought he might take a swing at me or even pull out a gun. So instead of really telling him off like he deserved, I politely just asked this scumbag to be a little less racist the next time around.

About ten other people witnessed what happened. One lady went up to the guy who had been discriminated against and asked if he was okay. But other than that, no one said a word.

After a very fleeting surge of courage, I ultimately wimped out pretty hard. And everyone else? Well, they just watched.

We all failed. And because of this, the bully won.

The whole event left me deeply shaken. As I contemplated what I had just witnessed, the only thing that brought me solace was the fact that it was Nov 7th. On Nov 8th everything would go back to normal and this disgusting cockroach would have to slink back into the dark shadows with all the millions of other closet racists Donald Trump has emboldened this election cycle.

November 8th.

Okay. Scratch what I said about November 8th.

As we watched the election results come in that night and it appeared Trump was going to win, I literally couldn’t talk. I went numb — catatonic.

Shock. Sadness. Disgust.

I went to bed before the final results were announced hoping against hope that I’d wake up to some miracle.

November 9th

I woke up. I immediately checked my phone.

Donald Trump. President Elect.

WTF!!??? Seriously??

We are in deep fucking trouble, America.

November 10th

I can remember being upset when Bush won in 2000 and even more so in 2004 because it felt like the Dems really blew that one. But this whole Trump thing hurt in a way that was on an entirely different level from any other normal Republican. This was supposed to be the election where Hillary won in a landslide and the country sent a loud and emphatic message to the rest of the world that we reject bigotry in all its forms. This was supposed to be the election where America showed the world what values we stand for.

In the end, I think we did show the world what we stand for. But sadly we revealed ourselves to be a very different America than the America I thought I knew.

To me, electing a racist reality television star over the most qualified nominee we’ve ever had is a slap in the face to all women. As a nation we just told women to go back to their place in the kitchen.

Sit down, woman. You don’t belong here.

But this election was more than just a slap in the face to women. It was a slap in the face to immigrants to Muslims and to all minorities. To all these people, America just said “your lives don’t matter.”

November 10–15

It has taken me almost a week to process everything about what just happened to our country. After grieving for a day or so, I spent the next couple days sticking my head in the sand and ignoring all news about the election. I couldn’t take it. I was too depressed and angry.

I finally started reading the news again on day 3 of the Trumpocalypse. But I decided not to write anything until my mind was clear I’d really recovered from this state of depression.

So now a week has passed and here’s what I have to say:

I have read about a million articles analyzing the election. I have processed everything there is to process and I’ve come to the conclusion that Trump voters aren’t really racist —  they are just regular people like you and me who felt ignored and left behind by an increasingly globalized economy.

Well that, and they fucking hate Mexicans.

In all seriousness, I’ve read so many articles and blog posts that tell the story of the “non-racist” Trump voter. These articles explain how it wasn’t about white-identity politics. It wasn’t about hate. This election was about the economy and jobs.

But here’s the thing — this storyline is complete garbage. Seriously, it’s fucking offensive. We need to stop normalizing the most abnormal presidency in the last 100 years.

Of course not every Trump voter is a card carrying KKK member. That would be insane and I don’t think anyone was ever really claiming that.

But if you vote for a racist candidate who promises to take away the rights of minorities simply because you think he’ll do a better job on the economy, that is not right — that is not what America stands for. You might not be a “textbook racist” but there is an extremely high chance you are someone who just doesn’t give a fuck about others.

I suppose that is slightly better than being a full-blown racist, but not by a lot. Because at the end of the day, whether you hate minorities or not, your intentions are irrelevant. When you choose to prioritize your own economic interests above the basic rights and freedoms of your fellow citizens you are effectively saying “Fuck you Muslims. Fuck you Mexicans. Fuck you, women. You don’t deserve the same rights I deserve and truthfully, I don’t care what terrible things happen to you, as long as I get an extra $375 on my tax refund this year.”

That, in my opinion is the biggest problem with America today. It’s not that the whole country is racist. It’s that the whole country (both conservatives and liberals alike) are indifferent to the suffering of people they consider “other.”

And the whole idea that you can separate bigotry from the Trump presidency is nonsense.

Here’s an analogy. I’m not sure it’s the best one but it’s the best I could come up with.

Racism and sexism are kind of like olives. People who like olives often really love olives. And people who don’t like olives don’t just mildly dislike them, they find them utterly disgusting.

The people who voted Trump but claimed they weren’t racist are basically arguing that they ordered a veggie pizza and all the things about the pizza were great except the olives. So when the pizza comes out they’ll just pick the olives off.

But here’s the thing. They didn’t order a veggie pizza. They ordered olive fucking tapenade!!!

When Trump comes out on DAY ONE of his campaign and says that Mexicans are rapists, anyone listening knew that olives were the main course of his campaign. They were baked in and inseparable from the jump. Pretending that Trump is a veggie pizza is simply offensive.

Now, I am not writing this post to shame people. I understand that people feel desperate and when you are desperate you make choices you’re not always proud of. I don’t blame these voters for their choices any more than I blame the guy in the street selling drugs because he sees no other options for employment. But what about the people who were not desperate? What about those Trump voters solidly in the middle or upper class?. How do they justify their votes? I want to have compassion for these voters. I want to understand. I want to be openminded. But it’s hard.

 At the end of the day, the bully on the subway might only represent the views of a very small minority of American citizens. Let’s say 5%. But when 95% of the population idly stands by and watches as the bully abuses his victim, we end up in a situation where the bully on the subway somehow ends up becoming the leader of the free world.

America, we failed. We didn’t stand up for what was right. We chose to be silent in the face of injustice. We chose to vote our pocketbooks at the expense of others. And I’m afraid to say, we got what we deserved.

I’ve come to accept that Trump is my president. I really do want to give him a chance. I want to believe that the hateful and divisive things he said during the campaign were just campaign rhetoric that won’t become policy. But a week after Trump is elected when you hear that Trump named Steve Bannon, an indisputable bigot as his chief strategist, it’s hard to hold out hope.

So now more than ever, I think it is up to all of us to double down on racial and gender equality. Now more than ever it is time to speak up for our Mexican and Muslim brothers and sisters. Now more than ever it is time to fight for justice.

We royally screwed up this election because we failed to stand up to the bully. Let’s not ever do that again. When we see injustice, we owe it to ourselves, to our country, and to the world to speak up.

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Why I invested In Pearachute

pearachute image

I recently made my second angel investment. It’s in a company called Pearachute started by my former co-founder at GiveForward, Desiree Vargas Wrigley. It’s a subscription based service for children’s activities — think Class pass for kiddos.

Though I am new to the investing world and haven’t yet developed a full framework for evaluating investments, in general I am looking for four things: great CEO; great team; big market; real need. Pearachute hits all of these criteria for me.

Here’s why I invested.

 1. Great CEO

First and foremost I’m looking for a great CEO, and Desiree checks this box.

As Mark Suster has famously stated, investors invest in lines not dots — meaning when you are opening your wallet, more data points > than fewer data points. As a rule of thumb, investors want to invest in people whom they trust and already have an existing relationship (a line) rather than people they have only met once or twice (dots).

In the startup world, I have no longer line than my connection to Desiree.

We had the opportunity to work together over the last eight years on GiveForward and I have an enormous amount of admiration and respect for her. She’s smart, hungry, passionate, empathic and her mind is always thinking about the future. I’ve seen her help pioneer an entire industry (crowdfunding). I have no doubt she can help pioneer another.

2. Great Team

Great companies are built by teams, not by individuals. The best CEOs are the ones who build the best teams around them.

With Pearachute, Desiree has done just that.

When she first told me about Pearachute my immediate response was, “this sounds amazing. You need to hire Erica” (our first employee at GiveForward).

With a smile, Desiree responded, “I already did.”

My heart lit up.

Recruiting is probably the most highly leveraged activity a CEO can spend time on. This is even more true when you’re recruiting your first five to ten hires, as these early team members will shape the DNA of the company for years to come. Hire great people early on and your life becomes exponentially easier over the next three to five years. Your chances of success also skyrocket.

But a startup team isn’t just employees and co-founders. It consists of investors and board members too.

Great CEOs recruit up just as well as they recruit down.

So when Desiree told me that some of our early investors in GiveForward, David Cohen (CEO of Techstars) and Sam Yagen (co-founder of OkCupid/former CEO of Match Group) were thinking of investing in Pearachute, my decision to invest became even more of a no-brainer. The reason wasn’t just because these guys are so called “brand name” investors, but more importantly because they are both incredibly smart and supportive and have a relationship with Desiree that goes back almost six years. Both sides of the table are going in with eyes wide open and that’s a wonderful thing. Again, it’s about lines not dots.

The final piece of any startup team is your board. As a CEO your relationship with your board is probably the most important relationship outside of the relationship you have with your co-founders. It is one of the few relationships that can either make or break a company. When Desiree told me that two people she’s known collectively for over a decade, Sam Yagan and Paul Lee (Managing Partner at Roniin) were going to sit on her board, it was icing on the cake.

Great CEOs recruit great teams and with Pearachute I think Desiree has brought on some of the best in the industry.

3. Big Market

I won’t spend too much time on this one because it’s pretty straightforward.

If you are optimizing for upside, big markets provide the greatest opportunity for outsized returns. As an investor, ideally you want to invest in the company that is going to execute the best in the biggest market possible.

The market for kids activities is estimated at $32B. For me, this checks the box.

4. Real Need

The last part of my investing checklist is about impact. I only want to invest in companies that solve real problems. Pearachute does just this.

When I was at the Pearachute office last week, I sat in on a phone call from a inbound investor (and father of a toddler) who was hoping to invest in Pearachute’s next round after reading about Pearachute in Techcrunch.

He pretty much started the conversation by telling Desiree how he viewed the problem in the current market:

“I have a three year old and when you have a three year old, you have no idea what they are going to be interested in. Plus kids at that age lose interest so quickly. The problem with the way things work now is you spend $250 to sign your kid up for soccer and get locked into a twelve week program only to find out on week two that he hates soccer and doesn’t want to go.”

When Desiree first told me about Pearachute she pretty much explained it like this.

“I have a three year old and when you have a three year old, you have no idea what they are going to be interested in. Plus kids at that age lose interest so quickly. The problem with the way things work now is you spend $250 to sign your kid up for soccer and get locked into a twelve week program only to find out on week two that he hates soccer and doesn’t want to go.”

It was uncanny how the investor and Desiree were saying the exact same thing. It was like Deja Vu.

Pearachute is solving is real pain point for parents. Instead of paying $250 and getting locked into soccer for the next three months, a $99 monthly membership on Pearachute allows your kiddo to take unlimited classes and discover all sorts of interests from art to sports to music, and language.

Pearachute gives children the opportunity to discover what they truly enjoy and reduces the pressure and financial burden on parents stressed out over trying to pick out the perfect activities for their kids.

It’s a win-win both for mom and dad and for the nino.


As one of my first angel investments, I don’t think I could have picked a company and team that I’m more excited about. And though I went through my entire investment checklist, truth be told, I probably would have invested no matter what. There are certain people who you’d invest in blind. It doesn’t matter what their idea is. Whatever they are doing next, you want to be part of it and get in on the ground floor. Desiree is one of those people. I’m pumped to see where this goes.

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The Best Books to Read in 2016


I’m trying to put together my reading list for 2016 and looking for suggestions. What were the best books you read in 2015 that I should read this year?

Here’s what I read in 2015 if it helps spark any ideas for your 2016 reading list.  If you want to start a discussion about any of them, hit me up @ethanaustin


The New Jim Crow:  Mass Incarceration in the Age of Colorblindness by Michelle Alexander

MUST READ:  If there is one book I would recommend reading in 2016 it is this one. I think we are at a pivotal moment in history right now in the fight for racial justice and equality. This is the most illuminating book I’ve read on the subject.  In methodical detail, Michelle Alexander ties together the various components that have created our system of state sponsored oppression leading to the incarceration of millions of African Americans and people of color.  This book was a game changer for me. If you are curious about racial equality and why the Black Lives Matter movement is gaining so much momentum, I highly recommend you to read this book. It will be impossible to stay silent on this issue once you do.

Give and Take:  A Revolutionary Approach to Success by Adam Grant

Good Read. A quasi-business-slash-self-help-book, it’s an easy read filled with lots of fun stories and science to back up the message. The central theme is that people who consistently give to others without the expectation of return tend to wind up the most successful people in life.

The New New Thing:  A Silicon Valley Story by Michael Lewis

Good Read.  I love Michael Lewis books and had never heard of this one until recently. The book was written in 1999 about Silicon Valley so it’s interesting to see what’s held up and what hasn’t.  The protagonist is a guy named Jim Clark, who is most famous for bringing Marc Andreessen out to the Valley to build Netscape.  The book is not as heady as some of his other books like Flash Boys or the Big Short. It’s not as good as those either but it’s still fun to read as Michael Lewis is an awesome writer and Clark was a fascinating guy – kind of like the  Elon Musk of the late 1990s.

Superintelligence:  Paths, Dangers, and Strategies by Nick Bostrom

Horrible Read!!!  Ever since I randomly stumbled into a Ray Kurzweil speech in 2010 I have been super-fascinated by the subject of AI.  Unfortunately, I thought this book was a clunker.  Though it was highly touted by guys like Elon Musk and Bill Gates, I found it to be nearly impossible to read and inaccessible to people of average intelligence like myself.  If you are interested in the subject of AI you can get the gist of the book in one twentieth of the time by reading the ABSOLUTELY AMAZING Wait But Why two part series,  The AI Revolution: The Road to Superintelligence

Man’s Search for Meaning by Viktor Frankl

Good Read.  Not much to say here that hasn’t been said.  It’s a classic.

The Circle by Dave Eggers

Good Read.  This is an eerily spooky farce on Silicon Valley and where things might be heading in the future.  Think:  a modern take on 1984.

Between the World and Me by Ta-Nehisi Coates

Meh. This book has received a lot of praise but I was a little disappointed.  Ta-Nehisi Coates is probably my favorite writer so my expectations were really high and it just didn’t do it for me.

Life on the Outside:  The Prison Odyssey of Elaine Bartlett by Jennifer Gonnerman

Good Read.  If you’re interested in racial justice issues, I’d recommend reading this book after you read the New Jim Crow.  It’s a narrative told through the story of  Elaine Bartlett who goes to prison for nearly 20 years for her first drug offense.  Whereas the New Jim Crow is very academic, this book is gritty and real and illustrates in human terms the horrible effects of our country’s racist drug policies and criminal justice system.

Asylum Denied:  A Refugee’s struggle for Safety in America by David Ngaruri Kenney.

Great Read. The book was written in 2008 and chronicles the story of a Kenyan seeking asylum in the US after he had been tortured by his government  for leading a farmers’ protest for higher wages.  Co-authored by Philip Schrag a Georgetown immigration law professor, Kenney’s narrative shines light on the heart-breakingly inequitable laws we have in the US surrounding the asylum process.  Many of these restrictive laws were put in place by congress after the 9/11 attacks based on irrational fears that terrorists could use the asylum process to sneak into the country.  Incredibly powerful and timely for anyone concerned with the Syrian refugee crisis, I read this book in Dec 2015 amidst all the fear-mongering taking place after the Paris and San Bernardino attacks.  I think what was most powerful about this book was that the introduction written by Schrag in 2008 seems so prescient today.   In it he wrote:

[Overly restrictive] statues and proposals such as these are based on the ludicrous idea that asylum is easy to obtain and that terrorists can therefore evade immigration restrictions by masquerading as refugees.  Actually, asylum applicants must go through an exacting examination based on documentary evidence to prove their identity and the truth and validity of their claims…a terrorist would be poorly advised to apply for asylum, because an applicant comes to the attention of officials who question every aspect of the individual’s life.

A Hologram for the King by Dave Eggers

Horrible Read.  This book was a bag of poop.  Not Dave Eggers best work.

The Art of Asking; or, How I Learned to Stop Worrying and Let People Help by Amanda Palmer

Okay Read.   I don’t think I learned anything particularly novel from it but it was entertaining and fun to read.  It was written by rock star and TED speaker, Amanda Palmer.  She tells her own story about vulnerability that is very real and honest.

Harvest of Empire:  A History of Latinos in America by Juan Gonzalez

Okay-to-Good Read.  I thought this book was interesting.  It tells the immigration story of Latinos in America and  how different each group’s story is.  It highlights, Mexico, Puerto Rico, Dominican Republic, Cuba, Guatemala, Panama and a handful of other countries I can’t remember. The biggest eye-opener for me in this book was how much Puerto Rican citizens suffer due to PR’s  limbo status of being an American Commonwealth.

Bossypants by Tina Fey

Good Vacation Read:  Easy, funny vacation read.  Good for when you need a break from the real world.


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How To Win At New Year’s (Or How To Never Feel Bad About Not Meditating Again)

45% of Americans made new year’s resolutions two days ago.

The rest of us ate a donut.

Let’s admit it. New Year’s resolutions kind of suck.

So here’s an idea for 2016: GIVE IT UP!

That’s what I did four years ago, and today I’m a happier, healthier and more productive person because of it.

With that one decision I expunged from my life the feeling of failure and self-loathing that would inevitably arrive every January 4th when I remembered how much I hated meditating and eating kale. (Side note: Fuck kale. Seriously.)

With the exception of super-annoying people like Tom Brady, who eats avocado ice cream for his cheat meal, most real human beings can’t just say “I resolve to do X” and then will themselves to becoming an awesome person.

As a species we are just not programed to work that way. Science backs this up. Only 8% of Americans will actually achieve their resolution in full this year.

So why do we continue setting ourselves up for failure every year in a game where the odds are so stacked against us?

For me, it was convention. It was simply easier to do what everybody else was doing than to actually think for myself.

When you realize the odds of a game are stacked against you, either play a different game or change the rules to shift the odds in your favor.

In 2012 I chose to play a different game. I finally quit making new year’s resolutions.

This didn’t mean I’d given up on self-improvement and resigned myself to a life of Tombstone pizzas and sweatpants.

when brittany leaves

I’ll admit at certain times in my life, I’ve given serious consideration to the Tombstone and Sweatpants route

Instead, I opted for different path to self-improvement.

In December of 2011 my friend Patty invited me to a new year’s day vision board party.

“A what party?” I thought to myself. “I am too old to be doing hallucinogens.”

I googled ‘vision board party’.

As it turns out, it was completely different from what I had been picturing.

A vision board party is where you get a group of friends together, cut out pictures from magazines of things you want in your lives and then paste them on a board that you can keep throughout the year . The idea is that by envisioning this life you want, you are more likely to manifest it.

I’ll admit I was skeptical. Going to this vision board thingy seemed like an awfully slippery slope to becoming a full-blown, new-age mystic.

All sorts of questions raced through my head.

Will I have to start listening to Enya? Will I start wearing patchouli? Is my future going to look like this? I’m not sure if I’m prepared to make this leap.

But my friend really wanted me to come. So I agreed to go. When I got there I was blown away.

First off, there was no Enya. Second, it was fun.

Creating a vision board gave me an opportunity to reflect on my past year, and more importantly, it gave me an opportunity to be purposeful about what I wanted out of life going forward. After a few hours of cutting and pasting pictures out of magazines I had a visual representation of the way I wanted my life to look like in 2012 and beyond. Since that time, I’ve made a new vision board every new year’s day.

Yesterday I pulled out my original board from 2012. Amazingly, about 80% of the things I put on it in 2012 have now become a part of my life.

For example, in 2012 I had never climbed a mountain before and it was something I really wanted to do. So I put a picture of a guy scaling a mountain on my vision board. I then hung my vision board over my dresser so that every morning when I got dressed I saw the picture of that guy scaling the mountain. This created a daily visual reminder throughout the year that mountain trekking was something important to me.

It was something I stayed focused on for the year and eleven months later I summited Table Mountain in South Africa. Granted this was a far cry from scaling Everest but it was a start in right direction. I loved the feeling of sitting at the top and looking out at the world. It was a feeling I couldn’t shake.


Summiting Table Mountain, South Africa 2012

The next year, I put another picture of a mountain on my vision board. That year, my wife and I got married on top of a mountain in Banff after a 7 mile hike with our families.
wedding photo banff

Hiking up the Plain of Seven Glaciers for our wedding in Banff in 2013

For our honeymoon we went heli-hiking in the backcountry of British Columbia.

Hiking Mt. Nimbus in the Columbia Mountain Range our honeymoon in 2013


The next year, I didn’t need to put a picture of a mountain on my vision board. I no longer needed a visual reminder. Seeking out the mountains is something that had become ingrained in me.

Why Vision Boards are Better than New Year’s Resolutions

What I love about vision boarding is that unlike new year’s resolutions that are binary and end in failure 92% of the time, vision boarding is more of a continuum.

 You don’t have to achieve all the things on your board in one year. Nor do you have to create narrowly defined goals of what you specifically want to achieve. (e.g one year I just put up tacos).

I like to treat vision boarding like OKRs where I hope to do maybe 60-70% of the things I put up on my board. For me, it’s more about starting down a path of making continual improvement than it is about hitting specific milestones and achievements within an arbitrary timeframe.

Four years after my first vision board, I have not accented any of the world’s seven summits. Nor have I even done any serious mountaineering yet. But what I have done is taken the first step — the hardest step. I’ve shown up.

Little by little, I have made hiking a part of my life and I’m so much happier because of it.

Yesterday, I was at REI and purchased an alpine jacket for a 10-day hiking trek my wife and I are taking this year in Patagonia. Nowadays, I can’t imagine my life without the mountains being a major part of it. I have my vision board to thank for it.

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The Four Most Powerful Words in the English Language

I believe in you

I believe in you.

These are the four most powerful words in the English language. When we share these words with someone, everything in the universe becomes possible.

Yesterday I met with a couple of GiveForward’s early angel investors. These were the dudes who bet on us in our first funding round in 2010 before crowdfunding was even a thing. They believed in us before anyone else did.

I told one of them half jokingly that while I appreciated all the advice he’d given us over the years, in all honesty most of his tactical tips on management and leadership went in one ear and out the other.

His eyebrows raised up as if to say, “well jeez, thanks…you dick.”

But then I said

You know, that’s not the point. It doesn’t matter what you said. It’s how you made us [my co-founder and I] feel. That’s the important part. Whenever we left a meeting with you we felt like a million bucks — like we could go out and tackle the world because you believed in us and you always let us know that.”

The ‘value add’ he created as an investor wasn’t his wisdom, it was his character.

As a founder, I’ve tried to model my behavior after his. For many years when someone would ask what I did at work my response was simply,

“I’m the head cheerleader. My goal is just to make people believe in themselves.”

Everyone Needs a Head Cheerleader in Their Life

When we build people up rather than break people down we achieve so much more in our classrooms, in our homes and in our companies. Study after study backs this up.

In a study conducted at Harvard, Asian women were given math tests. Before the first test they took, they were told to think about the fact that they were women (who are stereotypically worse at math then men). They later took a second test of equal difficulty, but this time they were told ahead of time to think about the fact that they were Asian (who are stereotypically good at math). The second time around they scored far better simply because they were primed to believe in their own abilities.

Similar results have been seen in African-American students who were given tests the day before President Obama got elected in 2008 and the day after Obama got elected. The day after his election test scores rose dramatically because having a role model in the white house temporarily freed the kids from self-doubt and internalizing negative racial stereotypes. (H/T Shawn Achor)

But it’s not just academic studies. The power of believing in people is real. I see it day in and day out.

Yesterday I got an email from a GiveForward user — a teacher at an inner city school where almost none of the students’ parents went to college. A few months ago she raised $3000 to take her students on college campus tours. As the money was rolling in she wrote that her students couldn’t believe that strangers on the Internet were donating to their trip. For many of them it was the first time a stranger had ever said “I believe in you.” Today twelve acceptance letters have come in and eleven of them have come from colleges where the students had toured.

They visited the campuses. They met with alumni from their high school who had gone through the same program. And now they are beginning to believe in themselves and their abilities.

The teacher asked if there was anything they could do to return the favor. I said,

“Make sure that the students know it’s their obligation to mentor the next class and then the class after that.”

If Anyone Has Ever Believed in You, You Have an Obligation to Believe in Others

I grew up in a very privileged environment. Throughout elementary school, high school, college, law school, and then in the startup world, both my inner circle and society at large told me I could do whatever I wanted. For most of my life I never gave any thought to the fact that this isn’t true for everyone.

I feel strongly that we need to make it true for everyone. If you have ever benefited because someone believed in you, then you have an obligation to believe in someone else.

Last night I got a text from a buddy who was one of the first in his family to go to college. When I met him a few years ago, he was trying to get his feet under him in the startup world. Today he’s absolutely killing it and was just recruited to join a venture capital firm. He texted me:

He said he would. I just hope he looks good in a cheerleading skirt.


Peak San Francisco

I was at a tech conference the other day in SF. My buddy was one of the speakers. All the speakers got a bottle of wine.

Buddy: I’m going to Shyp the wine home so I don’t have to carry it around all day.

[Shyp is an on demand shipping app where you take a photo of something and someone comes to pick it up and mail it]

Me: you realize that is pretty much the most San Francisco thing you could have possibly said.

Buddy: yeah, it was, huh? But I don’t want to carry it around all day.

Me: What if it’s shitty wine and the cost of it isn’t even worth the shipping costs?

Buddy: Oh, good call.

[He then proceeds to pull out another app that scans the bottle label and spits out the price of the wine. Upon realizing it was cheap wine, he leaves it on the table.]

I’m calling it right now. San Francisco has officially reached peak craziness. This town is nuts.

Why Crowdfunding Isn’t Enough

why crowdfunding isn't enough

When we launched GiveForward in 2008, we were innovating a brand new concept. The term crowdfunding hadn’t been popularized yet, Kickstarter was still months away from launching, and the idea that one could simply set up a site on the Internet and ask friends and family to contribute to a medical fund was completely novel.

Today, we are in a different world. It’s hard to imagine someone who hasn’t contributed to a medical crowdfunding campaign either for a friend, a family member, or for someone they read about in the news.

To date, millions of people have visited GiveForward and raised over $170 million for out-of-pocket medical expenses and life-saving treatments. We boast a net promoter score higher than Apple or Zappos and our office walls are filled with handwritten cards from users (we call them “hugs”) exclaiming how GiveForward has changed their lives. It’s been easy to feel good about what we are doing.

But the reality is we grew complacent.

Simply put, we stopped innovating. Until one day last year we finally woke up and realized that the industry we had helped pioneer had become commoditized — a giant indistinguishable mass of crowdfunding platforms all offering a nearly identical feature set. Even more remarkable than this convergence towards the norm was the realization that every platform, including GiveForward, looked and functioned almost exactly as it did five years ago. Complacency had steamrolled innovation.

So late last year we decided it was time to take a step back and reexamine EVERYTHING. We asked ourselves a single question:

Are we really solving the problems of our users?

When we opened up a dialogue with our community the answer we got back was a resounding no. We were only solving a tiny portion of the challenges our community faced. It turns out crowdfunding just isn’t enough. So we set out to build a better solution.

Evolving Beyond Crowdfunding

Someone going through an illness or a challenging life event needs much more than financial support. They also need meals coordinated and delivered, extra help with childcare, transportation to and from treatment, and a way to communicate updates with friends and family. Most importantly, they need a community to rally behind them and let them know that they’re not alone. Until now, people would have had to navigate four or five different sites to tackle all these needs.

Starting today, they will need just one: GiveForward.


This morning, we announced the launch of the new GiveForward, a centralized place where friends go to help the people they care about in many different ways — everything from sharing photos and “thinking of yous” to coordinating meals, sending needed wishlist items and raising money for out-of-pocket expenses. We want GiveForward to be the first place people turn when someone they know is going through a major life event. But just as importantly, we want it to be the place they come back to again and again to support their friend throughout their journey.

What’s really exciting for us is that we’re already seeing this happen. During our beta period of 1650 new GiveForward pages, we saw a 322% increase in returning users as compared to our legacy fundraising pages. People are coming back, sharing and giving in new and different ways. We see this as a beacon of promise.

Looking Towards The Future

Our new vision has made 2015 our most transformative year yet. This evolution beyond crowdfunding helped us attract a new CEO and some of Chicago’s best executive and product talent to our team. It also helped earn us our biggest partnership to date. This month marks the beginning of our partnership with Nationwide Insurance, a company whose mission aligns so much with our own. When we told them about our vision for the new GiveForward, we couldn’t believe how quickly they embraced it and moved to help make it a reality. Nationwide is a Fortune 100 company, but we’re lucky that they also happen to be one of the most innovative companies in the world. We believe that the new GiveForward will be built on partnerships like this one with companies that share our values and care deeply about making people’s lives easier when they need it the most.

For GiveForward, 2015 is going to be a year of taking what we started to the next level. In 2008 we pioneered the world of medical crowdfunding, but we didn’t go nearly far enough. Today we’re evolving the world of crowdfunding into something that truly solves the needs of people going through life’s biggest challenges. It’s exciting to be innovating again. Suffice to say, we’re through being complacent.

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