2020: My Year in Review

2020: My Year in Review

December 31, 2020

What’s an annual review supposed to look like anyway?

That’s the thought going through my head in the few weeks leading up to the final day of 2020. There are plenty of great examples and resources from people I admire and respect but this year I’m creating my own version.

I’m going to tell you the story of my 2020. After all, storytelling is kinda my thing so no reason to shy away from what I love most.

I had made it. The fancy office with floor to ceiling windows and beautiful art all around me. I had my modern office furniture assembled and set up to resemble Harvey Specter’s as much as possible. I didn’t quite have that setup but it felt like it. In my mind, the lawyer life I always dreamed about had been achieved. 

Fancy suits, Hermes ties, and Ferragamo loafers lined my closet. My beautiful leather briefcase from Italy had just arrived and when I went to the courthouse all of my old colleagues would remark on how I was finally in the big time. 

Don’t get me wrong, I love fashion, art, and design but those things didn’t mean I was actually living my dream. In January though, it felt like I was.

Except then school went back into session and my 15-minute drive to and from work became a 45 to 60-minute drive. I couldn’t make it home to see my aging dog Roxie at lunch. The hours were long. But worst of all the hours were boring. 

Was this really how I saw the next 20 or 30 years of my life playing out?

No, it wasn’t. 

I was finishing up my 2nd year teaching at SMU Law School and coaching the national mock trial team there and found that experience invigorating and wanted more. But the 40 hours invested on top of my normal lawyer job made it exhausting and stressful. 

I saw that a change was needed. I also saw what I love more clearly than ever before. Combining my training and experience as a trial lawyer and speaker with this love of teaching and helping people change the trajectory of their lives.

In February I tried the last case I would try as part of that law firm and ultimately one of the last cases before Covid shut the courts and world down. 

I wrote about this case before but I was defending a man who had killed his brother. No doubt about it. It was on video. He admitted it. He was devasted by it. 

But I was convinced 100% that he acted in self-defense. And realize, I spent the first 6 years of my career as a prosecutor. I’ve put murderers in prison for decades, if not the rest of their lives. This created an incredible weight on my shoulders. If I lost, my client’s life and his family would be forever destroyed.

The government wanted 25 years in prison. I wanted zero.

I won.

In this county, with these facts and these jurors, we were supposed to lose. And lose quickly. 

That moment hearing the words Not Guilty on the charge of murder showed me the levels I had reached as a trial lawyer. 

What else was left?

Photo by James Lee on Unsplash

In May I left my weekly paycheck.

Dallas was in a complete shutdown. The world was reeling from Covid.

I remember that conversation with my boss where I explained why I wanted to go out on my own. I needed to create my own way. I wanted to be a creator and founder. 

When I left, I told him he could accept my resignation immediately and not have to pay me or he could continue on because he had received a payout from the Covid relief bill for small businesses. I hoped I would get two more weeks of pay.

I crafted my resignation in a way that would make it easy for my old boss. I wanted him to be set up for success and do right by him. When he asked why I chose that moment instead of waiting since the world was shut down I told him that it felt wrong to me to take his money if I was planning to leave. 

I’m still proud of that moment. Ethics over some cash.

He was able to accept the resignation that weekend and did not need to pay me further.

I was on my own. No income. No clients. Just a vision of something greater.

The obvious decision for any lawyer is to start a law firm and that’s what I did with my long time friend and co-coach at SMU Law School. 

We are both trial lawyers and leaned heavily into that idea. Normally this would be great. In 2020, it meant very few cases came our way because the courts are shut down.

This leads me to the most interesting part of the story of 2020. 

I stumbled upon the world of Twitter in a serious way. I watched a live zoom call between Matthew Kobach and David Perell about crushing Twitter.

Talk about something I never expected to do but somehow became fascinated with this world. That’s when everything started.

I found Jack Butcher and Visualize Value. I took Design Fundamentals. Honestly, this is laughable. I can’t draw or design anything. I’m not a wiz at slide decks like Paul Millerd or John Meyer (two internet friends I’ve made this year). I had zero business taking this course but it seemed interesting. 

I laugh thinking back on it now. I remember seeing Jack’s designs and thinking how simple they looked. Surely I can do the same thing.

Fun fact...I’m no Jack Butcher.

But I still learned a ton about principles of design and figured out a way to embrace the concepts in my own art form. Speaking.

The other big thing in this course for me was seeing David Perell again. The guy just kept coming across my radar so I dove in a lot deeper to what he was about.

He wrote an article about his 10-year vision and I immediately signed up for his course Write of Passage. He thought bigger than just online writing. He had a vision. 

One thing that still stands out to me about that moment is that it wasn’t any of David’s marketing materials that convinced me. It was one article where he laid out his plans and thoughts. It’s a reminder to put your work out there. To build in public. You never know who’s watching or reading. That point will come up later.

Jack Butcher and David Perell are two of the most influential people in my 2020 and changed the trajectory of my life. 

As I signed up for Write of Passage which started in July, Jack also released a product called Build Once, Sell Twice in July.

I bought that too.

Those two courses showed me the possibilities of this online education world. Jack’s background in design was extremely similar to my background in the legal world. 

David’s WoP 5 showed me the power of cohort-based courses and community. 

In July, I had nothing going on. Cases weren’t coming into our law firm. I had time. A lot of it.

So I went absolutely nuts with WoP. I went to every session. I completed every assignment. I was meeting with people, creating small groups, and even set up a small group system that nearly 80 people joined to form daily accountability writing groups. Not only that, I attended 3 different mentor groups each week. And most of all, I was on Zooms nonstop. 

These were my people. The motivated, dedicated, ambitious, but friendly and selfless too. That environment led to 50 very close friendships. It led to probably another 50-100 connections with current students and alums.

It also created an energy on Twitter and online. More people started to find their way to this corner of Twitter. 

David and Will Mannon had created the thing so many of us were looking for in that moment of the summer of 2020…

Human connection.

Photo by Tim Mossholder on Unsplash

I’ve never seen a group of people become so invested in one another so quickly and deeply. 

I became close friends with people like Brandon Zhang who was 19 and just getting ready to go to Columbia University as a freshman. I met people like Andrew Barry and Charlie Bleecker that served as mentors. They will forever be some of my nearest and dearest friends that I would do anything for.

I can’t even name all of the people I met in Write of Passage but know that you all played a huge role in 2020 for me. I saw other friends launch companies like Greg Frontiero with Noowave and found inspiration in being on a similar journey. 

People who were huge on Twitter, in tech, in consulting, design, marketing, and anything else you can think of became a DM away that would be answered in 30 minutes. Need an essay edited? They would get it done that day. 

My July was spent deep in this world. Tweet, write, edit, zoom, class, repeat.

A new world had opened. Like Neo choosing the Red Pill, I saw it. 

No more boring office job with a long commute day in and day out for the next 30 years. Instead, I could create and build online. I could work remotely. I could travel and experience the world. 

The last trip I took was to Paris in January as I spent 3 days exploring the city solo. It’s a beautiful way to explore but as a lawyer, the cycle goes work, quick vacation, work. 

I wanted to live places and integrate my work into that environment. 

I want to wake up and surf, work, explore a place, and understand the rhythms and ebbs and flows in a place. Work integrated with life. Life. Not separate things.

In July I saw the way.

I created the idea of a Performative Speaking cohort-based course. 

I’ve outlined how the course came to be in a tweet thread before so I won’t go into that again at length but it was 3 months of pure energy, excitement, and exhaustion.

I always felt ready and not ready at the same time. It reminded me of being in trial. 

In October I turned the lights on, flipped the switch on my camera, and opened up the zoom room.

Would people show up?

They did. They all showed up.

I used everything I knew after taking Jack’s courses, David’s WoP, and also Tiago Forte’s Building a Second Brain.

Teachable, Circle, and Zoom was my tech stack. I ran 3 live teaching sessions each week. I added 2 office hour sessions each week. I ran CrossFit for Speaking (credit to David Perell for the inspiration with CrossFit for Writing idea) on 3 Saturdays.

I got help and advice from people I will never be able to pay back for their generosity, time, and help. 

Clay Hebert workshopped with me for hours and even came and did a guest session on The Perfect Intro (which was an absolute masterpiece). He saw early versions of the outline and vision. We talked community and structure and everything in between.

Justin Mikolay helped me work through ideas and refine what the Performative Speaking course would look like. He’s the former speechwriter for General Petraeus and General Mattis. He is a part of Gumroad and understands the creator economy and speaking. 

I became friends with these two people. I still can’t believe how lucky I was to have this happen.

David Perell talked to me whenever I needed to give me insight and guidance. Jack Butcher did the same. Not only did they inspire this journey but they gave me the help I needed to make it real.

They too became friends. 

My world changed fast. 

During my course, I had people like Andrew Barry and Julia Saxena that were in the cohort that would give me real feedback after each session. I learned so much from their insight and help. 

If you know me, you know that I love playing with time in my stories. This means we need to rewind and go back into August to build out more of how this all happened.


Real friends were formed through Twitter. 

One connection changed everything though. We called it Twitter Englightenment as a joke. We were all sub 500 follower accounts at the time. 

I knew Andrew Yu a bit from WoP. We vibed but hadn’t had a ton of interaction. So me and him chatted.

He was so legit.

Then Jamie Russo, (fun fact...an amazon best selling author now) reached out because of all the energy from the WoP 5 crew. We set up a call.

That quickly turned into a 3 way DM group called Twitter Englightenment. We turned that into a weekly Zoom call every Friday. 


No motives. No asks. Just a way for 3 guys to connect and talk about things we were facing, struggling with, or to celebrate each other’s wins. 

Unknown to me, on a James Clear post in August that asked for the best accounts to follow under 10,000 followers, Jamie put me on there.

“I’ll do you one better. Under 1,000. @robbiecrab. Watch this one in 6 months. Rocketship.”

A few people commented after and then another Twitter follower posted my account on that same tweet by James Clear.

I gained 2600+ followers in 24 hours. 

The things that don’t scale, make all the difference.

That Twitter Englightenment group of us 3 continues to talk in DMs on a daily basis and still have our weekly Friday Zoom call. We are all on the rocket ship.

This growth on Twitter matters because it’s where people started to associate me with public speaking, trial lawyer, and storytelling.

I followed that playbook from David and Matthew. 

I started June at 180 followers. As I write this I have crossed 8,150 followers.

Social proof is real. 

This takes us back to the world of Performative Speaking and after the first cohort ended. The course had a 95% completion rate. Unheard of in this world.

The results were an average of 44% increase in speaking ability from Day 1 to the finish. Live speeches in the class were mind-blowing. Beautiful, powerful, and most of all, transformational.

Success and the hype from students started to get noticed. 

Enter in Ali Abdaal. A brilliant creator. He has a YouTube channel with over 1 million subscribers. He has a Twitter with over 44k followers. 

He launched a video course called Part-Time YouTuber Academy and we connected through Twitter. After a zoom chat, he asked if we wanted to link up and be involved with each other’s courses. He asked if he could release our zoom as an interview in the course and followed up with an ask for guest workshops.

I said yes to everything. This was a big break. That’s a massive audience and the first cohort he ran had over 400 people in it. 

I taught storytelling and how to be a better speaker the quick and dirty version. 

This felt like the moment I made it over the wave. Big-name people were taking notice of what I was creating. More and more creators started reaching out to me. Podcasts started invited me on. Things were happening. 

Photo by Silas Baisch on Unsplash

But the stress was still high. It’s still fully on me to run everything. Marketing, outreach, sales, content creation, and so much more. 

Podcast appearances, content creation, DMs, Zooms, the grind is part of the process. 

So this brings us to the next stage of this year. The one that ended with Performative Speaking being acquired by On Deck.

Now I’m not sure but this is the first course I know that has been acquired. What a way to end 2020. But don’t worry, I’m not ending this review yet.

How did this happen?

In September I saw On Deck Writing announced and I knew the quality of what On Deck was creating. I wanted to be a part of this community.

So I applied. 

I got past the first stage quickly.

Then I was waiting.

During this time though I had become friends with Vik Duggal from our time in Write of Passage. We talked about what I was building and my experience. We talked about his experience and what he was building. But during this time he also tweeted about being a part of On Deck so I asked him about it. 

I told him my interest in the writing fellowship and that I was stuck in the process. He reached out and the next day I was in.

I would also later join Vik’s program called Consulting Club in December. He helped me bring my trial lawyer, public speaker, and teacher into one powerful package that delivers incredible value to founders with my consulting offer.

But back to October.

ODW started at the same time as Performative Speaking. Challenging but doable. 

Except I got Covid during this time. Nobody knew except those closest to me but for 3 weeks it was rough. I simply couldn’t run my course and really take part in ODW while dealing with Covid. 

So Max and Erik were kind enough to push me into ODW2. 

And then in the slack group one day recently I saw a message from Erik Torenberg. So I responded and we started a conversation just about Covid and me joining ODW2. Nothing that exciting just Erik being Erik. Generous and invested in his community.

A few minutes passed, maybe 30 or so and he reached out again. Something along the lines of you’re the public speaking guy, right? I hear you’re in this space. What are your thoughts on if something like that could work with On Deck?

Me being me, I shared my thoughts. I talked about the different options and approaches that could be taken. A small vision or a larger vision.

Short answer, Yes.

Long answer, we can change everything.

I wrote out a plan for what cohort 1 would look like for On Deck. No offer but I believe in giving away the playbook.

After all, nobody can be me. To do this right requires someone with experience, results, and also an ability to teach this stuff to other people.

That led to discussions with many members of the On Deck team. From Head of Candidates to Head of Growth to Program Directors, and ultimately to a final discussion with David Booth the CEO, and Erik Torenberg together.

We had something that made sense. The numbers were close but the impact would be huge.

I was talking to Gonz, head of growth, a few days before and he said the question that drives him is how can he help the most people become founders.

The question for me, how can I help the most founders attract the right funding, talent, and idea customers by telling their story and framing the narrative.

I knew On Deck was the place to achieve this result. The scale will be huge. The world-changing ideas contained in the On Deck community is hard to fathom and I know the multiplier effect a Performative Speaking course can have inside each of the fellowship groups.  

So we agreed on terms. 

Performative Speaking was acquired by On Deck to help supercharge the storytelling and communication of their founders and fellows.

I imagine I will look back on 2020 as one of the most challenging and rewarding years of my life. I started a law firm. I created a startup. 

My startup was acquired.

I joined a true rocket ship with On Deck.

I built incredible friendships. 

I no longer work in an office or sit in traffic. I created the life I wanted.

I did it the way I wanted to do it.

Maybe I’m not Harvey Specter but that’s because I’m creating something better.

I created the Robbie Crabtree I want.

2021 looks good but only because 2020 got me here.

Connect with me: Robbie@beondeck.com

Follow me on Twitter: @robbiecrab

Title Photo by NASA on Unsplash

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