On Entrepreneurship, Resilience and Starting from Scratch with Landon Sanford

One morning I stumbled upon Landon's post and couldn't stop being amazed by his voice of perseverance.

I quit my job. I'm starting a new company. Ideally, I'm hoping that this was my last "real" job. Correction: this will be my last real job. I am going to keep starting things until something works out. I don't care if it takes months or years, I'm going to be a founder. I've only had failures so far with startups. But at this point another failure doesn't scare me: regret is the bigger fear in my mind. Regretting not reaching my full potential or regretting a day where I look back at my life and wonder if I played it too safe. So, I'm taking the leap. More failures to come. “The biggest risk is not taking any risk.”

I told him about my book, "Starting from Scratch," and he giggled and said, "I wish I had a book like that when I started. Starting from scratch is very lonely and something we entrepreneurs need to do all the time".

Like many people I interviewed for my book, Landon, too, started working early and built a solid way to learn by doing. Growing up in South Carolina as a teen, Landon's summer job was to offer shuttle pick-up to the beach and back and was making great money from tips. Post-graduation, he dabbed into many different areas. He worked in investment banking and even door-to-door book sales in Texas, which "built the rejection stamina he needed to have as an entrepreneur ." Then he applied for 70 jobs and got rejected by all, but a knee injury that placed him in 8 months recovery led him to decide "No TV until he starts a company," and so he did, and he raised 1.5M for it too.

The startup Landon founded didn't continue to grow, and he decided to close shop and get back to the corporate role. He found a job with Google but couldn't stay there because "Once you taste the taste of freedom, nothing else tastes the same," and since then, he started many startups and raised money for them all.

Landon's path is fascinating and is worth following because he knows the founder's way is his way and owns it. Landon attributes his resilience and perseverance to not having plan B "just like the Dark Knight Rises who jumped without a rope," he says and laughs.


The Learning Mindset

On the road to entrepreneurship, Landon found the need to learn to be self-sufficient at the beginning before there's a team or funding, and for him waiting is never an option. I asked him to list what he learned and how he decides what information he misses:

  • Needed to learn design > took design courses.

  • Needed to learn how to be a product manager to better work with developers > took product management classes and read product management books.

  • Realized he needed to be better at public speaking > trained and set a goal to have a TED talk.

Landon's learning mindset is part of his growth, and according to him, the best way to learn is by "getting into the mud."


On Building Resilience

I reminded Landon about a post he shared. I read it out loud for him "I've still only had failures so far in startups. Low moments like running out of funding, being fired, going below minimum wage, letting teammates go, making the wrong decision, etc. But since I quit my corporate job, my plan has been to keep starting businesses until one works. And that will be this one.".

So he smiled… to himself really, from the side it looked as if he was forgiving himself and then he said: "Failure is not as scary as people think it is! there will always be swings and misses - it's OK". Admiring his resilience, I had to ask what he does for himself.

Landon admits resilience is part of his identity and has tried many ways to build his mental health. Last year he read over 30 books, and these days he likes to start his mornings with quiet reflecting on his day ahead.



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