Post #200
What have I learned writing online..
Three and a half years ago, I hit publish on an article called “The Secret Skill for Entrepreneurs: A Lifelong Quest for Learning.” I believed in every word. Reading it now, I appreciate how far the craft has come.
That first post reached almost no one. This week, I’m writing to readers in all 50 US states and 107 countries. From Marc in South America to Sheo in India. From founders in Brooklyn to operators in Berlin.
I’m based in Rapid City, South Dakota—not exactly the center of the startup universe. Writing changed that. It dissolved geography. It turned a small city in the Black Hills into a node in a global conversation about building companies.
Putting yourself out there is hard. It’s also one of the best decisions I’ve made.
What 200 Posts Taught Me
About a year in, a founder from New York City applied to Wildfire Labs. When I asked how he found us, he said he’d been reading the newsletter for months. A founder from the startup city, seeking out a program in South Dakota, because of words on a screen.
That moment rewired how I thought about this work.
Over 60 teams have come through Wildfire Labs in the past three and a half years. These articles are, in many ways, a shadow of their journeys. The frameworks that show up here get tested in real companies. Much of what I write ends up in our Wildfire Labs app, guiding founders through their six-month journey with us.
The posts that hit hardest weren’t the ones I thought were cleverest. They were the ones that gave founders permission and language for things they already sensed but couldn’t defend.
The $100 Trillion Disruption went viral—100,000 views—because it helped people see second-order effects they hadn’t considered.
The Cockroach Strategy resonated because it gave founders cover to build differently than VC orthodoxy demands.
The Measurement Paradox named a tension founders feel but struggle to articulate.
Seed-Strapping provided a framework for a strategic choice that didn’t have good language.
The historical parallels—Edison, Emily Roebling, Amundsen—work because they provide air cover. “This is how the Brooklyn Bridge got built” is easier to say to a skeptical board than “I have a hunch.” The history is dessert. The permission is the meal.
The Team
I write. But I don’t do this alone.
Tom Olson is my copy edit guru. He reads every article and delivers humble, constructive feedback that makes the work better.
Mike Vetter is my sounding board. He’s always up to help me sharpen a message—or tell me I’m going in the wrong direction. Both matter.
Priya Singh and Hailey Forrest make sure the trains run on time. They turn articles into LinkedIn posts, broaden the reach, and handle the operations that let me focus on writing.
It’s a team effort. The byline is mine; the work is ours.
The Promise
Here’s what I’m committing to for the next 200:
More personal experience. Less Edison, more “here’s what I saw at Wildfire Labs last month.” The historical parallels will stay—but only when they’re inevitable, not constructed.
Keep it free. Founders in the early grind shouldn’t hit a paywall to learn. That won’t change.
Keep showing up. Weekly, for another 200.
One reader, Paul Cavanagh, captured what I’m trying to do better than I could:
“Your articles show you have been in the trenches doing the doing and have been able to reflect on what happened and give a great framework on how to think about challenges and do them better—all in a genuine and heartfelt way.”
That’s the goal. Trenches, reflection, frameworks, heart.
The Ask
This newsletter will stay free. I’ve been a founder. Cash is always tight. Paying for content like this is a nice-to-have that rarely becomes a must-have. I remember that.
I’m at a stage in my career where it’s time to help and give back. So many people invested time in me, gave me second chances, helped me when I didn’t deserve it. If I can share some of these hard-fought lessons, this is a good way to do it.
But producing this takes real resources—research, editing, design, distribution.
Many of you reading this are no longer early-stage. You’re operators, executives, investors, advisors. You can afford to help.
If this newsletter has been valuable to you, consider becoming a paid subscriber. Your support funds the team that makes this possible and keeps it free for the founders who need it most.
If paid isn’t right for you, here’s what helps just as much:
Forward this to one founder who needs it
Reply and tell me which post changed something for you
Share on LinkedIn with your take
One Question
I want to make the next 200 posts better than the first 200. Help me aim:
What do you want more of?
Historical deep dives
Field reports from Wildfire Labs founders
Tactical frameworks and checklists
AI articles for founders
Reply with your answer. I read every one.
200 down. 200 to go.
Thanks for reading.
— Todd
Congratulations Todd on your amazing run of articles and different business topics. I’ve told so many people you are teaching PHD level classes for free and they should take advantage of them. I may not read them all but I sure enjoy all the ones I do read. Keep up the great work!!
I ADMIRE & CELEBRATE with WILDFIRE LABS & MR.TODD the 200th Post milestone and recognize it’s Worth as an Entrepreneur who has benefited by using the WISDOM of the posts and also as a reader.I request to put all these 200posts in WILDFIRE Archives section.
Fifty years from now,when the Startup History will be written,WILDFIRE LABS and MR.TODD, will be remembered for their contributions. I, as an entrepreneur, and,as a person, shall remain ever Grateful to MR.TODD for the impact MR.TODD posts had on me,as long as I live.
*- It’s like celebrating 200 insightful analyses and groundbreaking ideas that have shaped startup thinking.
- the frameworks and features, make these 200 posts, a treasure trove of knowledge that can be continually explored.
- in fact many a times I revisit the posts and I always find something that I read and didn’t apply and then I apply.
- Though Mr. TODD classified posts in hardest hits and cleverest —I Believe all of them are Classic articles,and provide timeless wisdom objectively though relevance may be subjective.
- As Startups now face new challenges, specially that ideas get copied overnight with AI and Tech, MR.TODD posts provide guidance on how to adapt and thrive.
- The intersection of strategy from history and from real life experiences, promoter leadership, and innovation has always been MR.TODD’s focus, and it shows.
- MR.TODD always shares lessons based on his own entrepreneurial journey and his observation of many founders and investors.
Entrepreneurship is hard. It’s not easy. It is tough. It is exhausting. But having guidance of MR.TODD is crucial to my success. MR.TODD’s many frameworks really made me to do a self-assessment about who I’m and what my core competencies are, because, particularly as an entrepreneur, I’m always being challenged. That is part of entrepreneurship, and that’s part of the journey.And,these posts made my journey smoother.
Well,I take liberty to comment on some of MR.TODD observations:
—What 200 Posts Taught Me: Me—Yes,I realised these articles & frameworks were tested in real companies.
—The Promise:Here’s what I’m committing to for the next 200:Keep it free.—Me—I’m GRATEFUL and so will all the beneficiaries be.I had earlier also acknowledged the generosity of free of cost advices.
—The Team —It’s a team effort. The byline is mine; the work is ours.—Me—“There can’t be a better statement of Teamwork.”
—One Question:My request—1.please share more of MR.TODD personal experience of entrepreneurs journey as those stories motivate. 2.pl.make a software checklist tool of the frameworks.
GODWILLING I look forward to read 2000 th post by MR. TODD.