Ryan Gaertner

Builder | Co-Founder & former CEO @DubClub_win | Stanford x2 @Stanfordfball @StanfordGSB

[Ryan Gaertner @Ryan_Gaertner]

“Ryan’s Reflections” #0: 🚀 Kicking off weekly tastes

I recently stepped down as CEO of DubClub after 4+ years growing it from scratch to $100M+ GMV. I learned a lot and enjoyed the growth alongside our customers, our team, and our investors. Along the journey and especially now, it seems obvious to me that I could have built + led + scaled much better in many ways. While supporting my co-founders in the transition, I am carving out time for deliberate reflection that I hope is useful to a growing audience of aspiring builders regardless of where you are on your journey.

Starting next week, I am launching “Ryan’s Reflections” — weekly bite-sized “tastes” with an essential learning that blends literature and personal experience. Every post will follow a specific format and cover topics like building, leading, and scaling. The main post will share a short “taste” or insight, with a pinned comment for viewers to get both a content recommendation and practical context from lived experience. Everything you read will be coming from my brain and my gut, hence "Ryan's Reflections"… not "ChatGPT's Reflections" or "Perplexity's Reflections".

I’ve personally seen AI very quickly take on lower-leverage work. Going forward, I believe the real challenge for many of us is to deepen our knowledge about how we can use our time in the highest-leverage ways possible.

I am excited to see what others think and learn from your perspectives. Please comment on the posts or send me a DM — I will read everything. And if posts receive crickets, that is fine too. My goal is to build, learn, and grow in public.

As we established at DubClub: Win More Together™.

[Ryan Gaertner @Ryan_Gaertner]

@akothari @ivanhzhao @NotionHQ @ivan Congrats on the full circle @akothari

[Ryan Gaertner @Ryan_Gaertner]

Helpful perspective from @karrisaarinen who has led @linear to become one of the most beloved products in one of the most competitive categories

Shouldn’t real mastery be measured by the ratio of inputs to output i.e. leverage?

[Karri Saarinen @karrisaarinen]

The fallacy of this is that more creates more. More hours, more hiring, more something.

And it is true in a sense. If you put in more work, more work will happen. But I think for most startups, the leverage is really in how differently you approach the problem, how well you cultivate your team, and the strategy.

Any large company can outspend you on hours. They have thousands or tens of thousands more people, spending more hours. If hours worked were the metric, every large company and government organization would always win and do the best work. More hours, better output.

This thinking is often representative of younger founders, where the startup becomes their identity and life. They have a hard time doing anything else, and cannot understand that your work is not the person that is you. But activities outside of work can grow you as a person too and make you do better work.

I’ve never worked this way. As a designer, I always saw the need to take a step back, to take a break. At times, I might work 12 hours or 16 hours, or whatever amount was needed, but it wasn’t the norm. You just can't grind design, you need inspiration. But taking that step away from the work, would give me more perspective, inspiration and I could approach the problem differently or I could just see the solution.

Grinding is never good for any creative problem, and startups or creating new products are often mostly about creative problem solving. Grinding works ok for email jobs, or where you just executing on very clear playbook.

With Linear, we’ve never worked this way. We work reasonable hours, 5 days a week. All of us founders have families. Many of our employees have families. I personally stop every evening, spend time with the family, cook dinner for the family, eat dinner together, and focus on things outside of work. Sometimes I work in the late evenings or weekends, but to me the pride is that I don’t need to. Company should be succesful without it.

My goal is to build a company that is sustainable in the long term, and doesn’t require heroics or personal sacrifices every single day.

There are times when our team is heroic. Launches, incidents, some other work that just needs to be done. They will work late into the night because they know it is the right thing. But we don’t require that every day or every week, and the more this happens, the more I think it is a failure of our company and leadership. The team and the leaders should always keep a reserve to use when something is needed.

Our thinking was also that quality, which we value, doesn’t emerge from working more or stressing people more. It emerges when you create the conditions for it to emerge. Often it is the appreciation, space, time, and how the person feels. A person who is rested will do better work.

I wouldn’t attribute much of our success to working a lot. The success came from having clear thinking, ideas, and focus to do the right things.

I sometimes wish we could move the culture more toward a Zen master.

Real mastery is not exerting the most effort. It is achieving the outcome with the least necessary effort.

[Ryan Gaertner @Ryan_Gaertner]

I'm not looking forward to the day when @NotionHQ starts charging for their agents 🤣

Been a joy getting to tinker with them bundled into my existing subscription

[Ryan Gaertner @Ryan_Gaertner]

Already done ... Took 15 minutes @perplexity_ai

Fancy seeing you at the top @AnthropicAI

[Ryan Gaertner @Ryan_Gaertner]

This will do wonders for tracking my weekly @OpenAI and @claudeai spend

Getting "invoice from Anthropic" email notices but haven't had an easy way to centralize the spend on a systematic basis, without building something custom myself

Keep the cool stuff coming @perplexity_ai

[Perplexity @perplexity_ai]

Computer now connects with Plaid to link bank accounts, credit cards, and loans.

Track spending in detail, build custom budget tools, and visualize your net worth alongside your investment portfolio.

[Ryan Gaertner @Ryan_Gaertner]

@felixleezd @felixleezd Agreed. Wdyt is the solution?

[Perplexity @perplexity_ai]

Today we're announcing the Billion Dollar Build.

An 8-week competition where teams will use Perplexity Computer to build a company with a path to $1B.

Finalists have the opportunity to secure up to $1M in investment from the Perplexity Fund and up to $1M in Computer credits.

[Ryan Gaertner @Ryan_Gaertner]

https://t.co/C4VGxAi7Oo

[Ryan Gaertner @Ryan_Gaertner]

Was skeptical of gstack after seeing it all over my feed

But I installed it this week and am very impressed

It takes @claudeai code thought partnership to another level

Thank you chef @garrytan

[Claude @claudeai]

Introducing Claude Managed Agents: everything you need to build and deploy agents at scale.

It pairs an agent harness tuned for performance with production infrastructure, so you can go from prototype to launch in days.

Now in public beta on the Claude Platform.

[Ryan Gaertner @Ryan_Gaertner]

🙌

[Alfred Lin @Alfred_Lin]

A CEO from one of our portfolio companies shared this with their team. I’m re-sharing it with their permission, because it resonated and reflects what all founders and CEOs should be communicating.

--
We are living through a period of compounding change. And in moments like this, the biggest risk is no longer making the wrong decision. It is moving too slowly while the world moves around you.

There are two paths. We can play defense:
- Protect what we have
- Optimize what works
- Wait for clarity

It feels safe. It isn’t.

Or we can play offense:
- Learn faster than the environment changes
- Use new tools to solve old problems in better ways
- And create entirely new strategies and businesses

That’s where the opportunity is.

Challenge yourself to do things faster and better than you have ever attempted. Stay uncomfortable. Stay on the front foot.

[Ryan Gaertner @Ryan_Gaertner]

Giddy to finally have @perplexity_ai Comet browser mobile app

[Ryan Gaertner @Ryan_Gaertner]

Every week something happens that makes me more excited (and nervous) for what’s coming with AI

Speaking to Perplexity Computer for 15 minutes resulted in 3 agents that now make starting my day so much easier…

- Filterable web-hosted dashboard showing status of deliverables (which I keep in @NotionHQ)

- Emails from contacts that aren’t in my CRM yet

- Suggestions for who to add to my CRM and proposed actions based on the inbound context

Kind of shocked me in a good way

3 years into using Perplexity too!

Thanks @AskPerplexity

[Ryan Gaertner @Ryan_Gaertner]

@AskPerplexity A good but long related article:

[Matt Shumer @mattshumer_]

https://t.co/ivXRKXJvQg

[Ryan Gaertner @Ryan_Gaertner]

Every week something happens that makes me more excited (and nervous) for what’s coming with AI

Speaking to Perplexity Computer for 15 minutes resulted in 3 agents that now make starting my day so much easier…

- Filterable web-hosted dashboard showing status of deliverables (which I keep in @NotionHQ)

- Emails from contacts that aren’t in my CRM yet

- Suggestions for who to add to my CRM and proposed actions based on the inbound context

Kind of shocked me in a good way

3 years into using Perplexity too!

Thanks @AskPerplexity

[Ryan Gaertner @Ryan_Gaertner]

My suggestion is to think of something you do daily that is kind of annoying, then @AskPerplexity if it can do the task for you

[Ryan Gaertner @Ryan_Gaertner]

@akothari Mine is starting to look similar 🤣

Trying to figure out how to integrate them closely with one another via Notion AI so it doesn't feel like I'm switching between the different parts of the ecosystem

[a16z @a16z]

"Not having a coding experience is becoming an advantage."

Replit CEO Amjad Masad:

"You don't need any development experience. You need grit. You need to be a fast learner."

"If you're a good gamer, if you can jump in a game and figure it out really quickly, you're really good at this."

"Coders get lost in the details."

"Product people, people who are focused on solving a problem, on making money, they're going to be focused on marketing, they're going to be focused on user interface, they're going to be focused on all the right things."

"I think this year it's gonna flip, and I think not having a coding background is gonna be more advantageous for the entrepreneur."

@amasad with @jackhneel

[Ryan Gaertner @Ryan_Gaertner]

@yourfinanceeguy @perplexity_ai @ChatGPTapp Yeah, 100% I remember when ChatGPT would hallucinate because it didn't have real-time information. It actually got some people into a lot of legal trouble, including lawyers being disbarred

[Ryan Gaertner @Ryan_Gaertner]

I'm thankful for my early use of @perplexity_ai way back in late 2022

Because of its real-time web search, Perplexity felt more reliable than @ChatGPTapp in the early days

This accelerated my comfortability with AI as a highly useful lever to get more of the right work done

[Ryan Gaertner @Ryan_Gaertner]

@AILearningPaths @perplexity_ai @ChatGPTapp Totally from the outside looking in, that feels like a huge leap, but honestly, as a user, it's felt pretty natural