A Retrospective on Catalog: Learnings, Myths, and Takeaways as a Founder

It’s been a few weeks since the conclusion of Catalog. I’ve been taking some time to reflect on the last three years.

The Catalog journey began while I was at Google. One of the big problems I saw was the difficulty small and medium businesses were having with advertising online, in particular getting quality photos to tell their story. Fast forward, we raised $3.1M with a team of 25+ FTE and 500+ contractors to solve the content problem. As founders, we were even featured on Forbes 30 Under 30 2020 for our work.

I wanted to share some myths, lessons learned, and things that still keep me up to hopefully provide insight if you’re thinking about starting a company or are currently in a start up.

Myths

There are a lot of start-up -isms. The need to go fast and break things. The pressure to have all the answers and also know you’re still learning it on the fly. There were a couple of things going into Catalog that I believed that I no longer believe from this start-up experience.

Do Things That Don’t Scale should be Find Scale Fast

In the early days of Catalog, I read a lot of blogs from Paul Graham. None are probably as popular as his article, “Do Things that Don’t Scale.” In it, Paul talks about the need to do things manually, founder grit, and focusing on a beachhead market. When I internalized the article in my early days, I read it as experimenting as much as I possibly could with sleepless nights and long hours.

The paradox of this philosophy is that one of the immediate questions you get when you go out and fundraise is: “How does this scale?” Investors want to know that if they put one dollar in that they will get two dollars out. The secret to scaling, from my point of view, is discipline. As founders, I think we over-index for novelty. Our name should be a name that no one else has, our marketing should be inspired, our product should be sleek. The truth is that it’s impossible to re-invent everything from the beginning (Elon Musk had a ten-year plan that was only part 1 for Tesla). I think it’s okay to copy+paste the majority of things (sales, marketing, website, etc.) and find the one or two things you are really innovating on and focus your mental energy on that. Scale today is less of an art and is more of a science.

It gets easier after you raise

There’s no sugar-coating this. I hear it often from founders that after we raise, you can hire that rockstar you wanted, build faster, or finally get that PR firm (or finally get sleep). There’s this fallacy that money resolves headaches. I was at a Xoogler chat with Qasar Younis, former COO of Y Combinator, and he was asked, “Does the funding or the founder make the company?” He left an impression when he said it was the funding. The funding enables the hiring, growth, and acceleration.

It’s a bit of a trick question because it takes the right founders to also prioritize spend.

That all said, I can say from my experience that funding does not make the job easier. As CEO/Founder, I began to see an expansion in my role in both breadth and depth. My plate exponentially expanded from worrying about my role to the responsibilities of my entire team.

The job gets harder after you raise, but you also get smarter.

Finding the mythical “hands-off” investors

I’m not sure where this originated from, but it’s something discussed amongst founders often. The goal of finding a unicorn investor — someone that will close fast, give you honest feedback, and remain hands-off to let you focus on operating your business. I do agree with a few of those points; however, I’ve actually appreciated having investors that are hands-on. In fact, there are many occasions where I leaned heavily on their expertise to save time, money, and mental energy.

For example, our lead investor, Moonshots Capital, had us do monthly board meetings (which sounds insane for most). However, the opportunity to press pause (which doesn’t happen often), review our learnings, and thoughtfully create a path forward with our board saved us from a lot of mistakes. All start-ups are extremely under-resourced, and anyone that is willing to give you their time should be cherished.

What I would do again

Often in start-up retrospectives, the reflections are focused on what one would do to improve or fix from the experience. These are two things I would not change for the future.

Training team members for their careers, not just the start-up

I can’t take personal credit for this. This philosophy comes from my prior manager at Google, Porntepp Ungvichian. While most managers focused on trying to build people up for their specific role (producing more product documents, increasing quarterly sales, improving customer satisfaction), Porntepp approached development differently.

He would ask us thought provoking questions like:

  • “What is it that you actually want to do?”
  • “What do you care most about?”
  • “How can I bring out the best in you?”

One of my philosophies on team development is that the success of the start-up is never assured, but the impact a founder/CEO can have on the company’s team is permanent beyond the business.

As with most start-ups, our budget allowed for only a few senior hires and many junior hires. As such, I knew the development of our people would be key to our success. I made time for weekly 1:1’s with all my direct reports and bi-weekly for the entire company. These 1:1’s were a melding of not only professional development, but often crossed into listening and providing a supportive ear in their personal lives too. I found that when we cared for the entire person and their whole journey, we brought out the best in everyone.

Discipline and Focus

Start-ups are notorious for constant experimentation. We too were guilty of that in the early days. We changed icons and webpages constantly. We tested multiple price points on different customer groups. We had dozens of different email templates.

We congratulated ourselves for moving quickly, but in retrospect the learnings were minimal. By constantly changing practices and materials, we built no real foundation to accelerate on or learn from.

One of the transformative points for us was when one of our investors, Mikhail Naumov, joined us in our office for three months. Mikhail was the co-founder of Digital Genius, which had at the time just raised their Series A with 26M total fundraised, and taught me the power of pause and patience. (It is also key to have good mentors and investors who are just a few steps ahead of you to guide you).

We morphed as an organization from a company that praised experimentation to one that elevated thoughtfulness and intentionality. For example, one of the most immediate things Mikhail did was bring rigor to our sales process. We were aimlessly trying different things: Adwords, cold calls, mailchimp, social media posts, etc. We stopped trying to do everything and just focused on one thing: cold e-mails.

We broke down all the various components of cold emailing and made it into a science. We were meticulous about every facet including: the number of new contacts, e-mails sent, win rate, call handling times, and messaging. Instead of trying to find a silver bullet, we made a silver bullet.

Here’s a sample of our weekly sales motion and metrics:

In a way, by making things “boring” and repeatable, we built a business that scaled.

What Keeps Me Up

There’s a lot I learned from Catalog, and it would take a much longer blog post or talk to go through everything. There’s also so much I still don’t have a clear answer on and at best only directional thoughts.

Start-up culture: All or nothing

When we think about start-up culture, we often think of workplaces where the hours are endless, the scopes are undefined, and you run at a breakneck pace. It is burnout culture.

In a startup, you want maniacs and diehards only. It’s not for everyone. A perfect example is Brian Chesky’s interview question, “If you had one year left to live, would you work at Airbnb?” Would you work on your start-up if this was the last thing you could do?

I get it.

But shouldn’t startups that stand to help more people be more inclusive of the whole person and their lives? Would companies benefit if we told people to take care of themselves? Or stopped glorifying workaholism?

What I think traditional startup culture misses is that there’s more to life than the company.

I don’t have an answer yet on what this new type of culture looks like, but I believe it’s an important one to look at if we want to build people focused companies.

On doing things right

In the last three years, I made more mistakes than I got things right. There were a lot of hard decisions. One, in particular, was when we had to do a 70% staff reduction in Q4 ‘19. The company had overspent over the course of the quarter, and it greatly impacted our start-up’s life. I proposed two plans to the board: a majority cut to our contractor staff and minimal full-time cuts or a steeper cut across the board. I was hoping that we would be able to retain all the full time members that had dedicated their time to Catalog; however, over the course of the board meeting, it was decided that the preservation of cash was more important to keep the company alive. It was decided that we had to cut 70% of the full time team.

I struggled a lot through this.

I spoke to a lot of other founders on what the right thing to do is. What we ultimately did was sit down with each person 1:1 and were straightforward with them. They weren’t being cut because of who they were or their contributions to the company. It was my failure to properly budget and account for changes, not theirs. In the end, it was well-received. Even though people cried, it was because they wouldn’t be returning to a job they loved.

What’s next

I’ve been trying to take a break. Originally, I wanted to take the time off to climb Kilimanjaro and visit friends. Instead, COVID hit and I felt it was my responsibility to step-up and volunteer. I’ve been giving my time and efforts to two amazing organizations: Frontline Foods and US Digital Response. (Please check them out by volunteering or donating).

I also want to take a moment to thank our investors: Moonshots (in particular Kelly and Jawhara), Luma (in particular Laurent, Matt and Danielle) , Techstars (in particular Anna, Ethan and Ryan), Day One Ventures (Masha) and our many angels (Johnnie, Francis, Dorothy, Wilson, Robert, Tony, Eric, Alan, Andy, Mikhail, Alex, and JB). I also want to thank our advisors: Gary Swart (Former CEO of Upwork), Aaron Magness (CMO at Brandless), Shaahin Cheyene and Keith Ferrazi.

In addition, I want to thank my parents. When we first set out to fundraise, my parents and I sat down at Cotogna in San Francisco where they offered to participate in our first round of financing and then invested in every round thereafter. This was particularly hard for me because in our final days, my parents still very much believed that we would pull a rabbit out of a hat (as we had done countless times in the past).

While this wasn’t the financial success many people thought it would be or hoped for, I remain hopeful that this is just the beginning. At 29, the best is yet to come.

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