The 7 Tools That Ran Our Business for the Last 7 Years

Becoming Dauntless

Dauntless’ seventh birthday has come and gone. Only 20% of startups make it past year five. IMO our unconventional approach to spinning out a tech startup is what kept us in the game:

➡️ Bootstrapping and passing on venture capital

➡️ Adopting new tech and pivoting as we see fit

➡️ Securing government contracts to fund our R&D.

What 7 Years as a Founder Teaches You

I surfed the blockchain hype, dodged NFT FOMO, and watched AI go from “that’s cute” to “please don’t replace me.” Here’s what I’ve learned: Your tech stack is your survival kit. Here’s mine, hype cycle-tested and founder-approved:

  • Sintra: AI Agents for everything from copywriting to financial model analysis

  • Descript: Intuitive audio/video editing

  • Notion: If it’s not in Notion, it doesn’t exist.

  • Squarespace: Idea to an aesthetic website in a few hours

  • Slack: Team comms because we don’t need email for most internal discussions

  • Canva: I know how to use Photoshop, but Canva is faster

  • Google Suite: Cal, Docs, Sheets, and Slides—oh my.

  • Honorable Mention: Pivotal Tracker (RIP—you were too good for this world).

If I were starting today, I’d go with Federated Computer and replace a lot of these under one subscription, thanks to open source, for less SaaS fatigue.

My biggest regret: Not listening to my intuition and sleeping on building a founder-led brand from Day One.

Markets tank, trends flop, platforms disappear. But a founder-led brand? That’s the moat no one can copy. Whether you’re a solopreneur or running a team, your personal brand is your unfair advantage. Build it, nurture it, and let it work for you.

To make posting less cringe, I poured all of my professional writing experience, journalism school learnings, and storytelling best practices from Ernest Hemingway to Alix Earle into a single AI system prompt.

Technical entrepreneurs, researchers, creatives, and founders are the ones who need to share their ideas with the world THE MOST and are THE LEAST likely to share their work online. I’ve been there, and if you’re there too, check out the Write Like a CEO System Prompt and create content that sounds like you: witty, sharp, and 100% human. Go grab it, plug it into your workflow, and let’s make your ideas impossible to ignore.

News You Need to Know About

Saved on Socials

The posts, memes, job postings, and videos that caught my attention this week:

Overheard on Slack

Enter the chat. What our devs are talking about…

  • “I can’t tell if this is rage bait or a cry for help” - on influencer power couple content.

  • "You need more miles on your life odometer before I want your advice."

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