Four Years, Four Lessons, One Big Change

At 32, after four years of building something from scratch, most people would tell you to keep going. Scale it. Hire more people. Open a brick-and-mortar. Follow the prescribed path to "success."

That's what I would have told myself 4 years ago.

But what if the prescribed path is just someone else's definition of success dressed up as my own?

Change is part of life. We started Tuckedito because we wanted to pursue our interests, and we're ending it to do the same.

I'm a visual thinker who wants to solve problems. I believe small business and entrepreneurs are a huge net positive to society.

After being a small business owner I realize many lack time to focus on their core business function. You're constantly putting out fires as well as dealing with all the other stuff that comes with running a business.

I enjoy "all the other stuff" and believe I'm pretty good at it.

So I'm starting a new business to use what I'm good at to help in an area I believe is important.

I want small business owners to have more time to focus on their core business function while I handle what I've been learning and loving: process optimization, AI automation integration, and systems thinking. I'll be combining my obsession with flowcharts and digital canvases (ha, nerd!) with AI tools to help businesses save time and money. (More specifics on this toward the end of this post)

For me, this transition isn't just about business, it's about staying true to who I am and what energizes me.

I've had four major shifts in my adult life that completely changed who I was. Each one felt like a huge risk because the future was uncertain.

But the future is always uncertain, it just doesn't seem that way unless you're consciously choosing change rather than letting change happen. Each major shift in my life that I've chosen has given me clearer perspective on who I'm becoming. Each identity I've killed has made space for growth.

"The only clear view is from atop the mountain of your dead selves." is an apt quote to define the feeling.

I haven't made one of those shifts for four years, and it feels time for another. To make that change I'll take along the the four lessons that four years of building Tuckedito taught me:

1. Sometimes you need to just jump in and figure it out.
2. The most mundane moments make the fondest memories.
3. The biggest risk isn't changing, it's staying still.
4. You have the power to choose your own path.

These lessons are now driving me toward Simple Flo.

What Tuckedito Really Was

Lesson 1: Sometimes you need to just jump in and figure it out

Tuckedito was born from daily conversations, for three to four years. Brendan and I would talk almost every day about starting a business.

Businesses all over the map. (Boots with foot warmer pockets, tombstones with screens, DiscussU a discussion based University)

We were stuck in that loop where you know you want to change but can't quite pull the trigger.

Just constantly ideating, not starting on anything.

The regret of standing still became heavier than the fear of jumping.

I can remember Brendan saying "We just need to sell something"

So we settled on an idea and just started figuring shit out.

By shit I mean: equipment we needed, recipes, around how much money it would be, what licenses we would need, what the brand looked like.

Then we burned the boats.

We both quit our jobs with no part-time income to fall back on. It was all or nothing. Time to build something we were proud of, out of necessity. And the strategy worked.

I realized business really is just about "figuring it out".

From my point of view, here's what we actually built by just "figuring it out":

For Ourselves: A business where we "relentlessly refined processes" until we had "software tools, kitchen techniques, communication templates" that made the business efficient and mostly pleasant to run. We proved you could work hard, have good people around you, and systematically improve your way to a profitable, sustainable business with built-in flexibility.

For Business Customers: A reliable and efficient service provider. We would provide exactly what we said we would when we said we would. This is how we operate on a personal level and how we operate the business. We never would overpromise. We do what we tell you we will do.

For Customers: A pleasant place to come order food. We wanted the food to be good and the service always to be pleasant, positive, and polite. Also, a place to bring people together.

This was done in tandem. Keeping a clear, honest, logical, and forgiving relationship made it possible.

Then we brought in Dom who really helped keep this up.

Dom was/is incredible. Ultimate positive morale guy. He has never missed 1 day. And every single time he shows up he has a positive attitude. Always smiling, always polite, always genuine, as well as always doing what is needed.

He is going to graduate college next spring and then improve whoever's business hires him next.

A Brotherly Bond Made Stronger

Lesson 2: The most mundane moments make the fondest memories

Brendan definitely kept me together at many points.

He's much better at staying even-keel than I am.

Getting into this business many questioned about "getting into business with family" as a disaster scenario for our relationship.

We always just took this advice with a smile and nodded, knowing that whoever said this was completely wrong. After 4 years I know we proved ourselves right.

Our esoteric interests align, and always have. Conversations we have together are much different than conversations we have with other people. And we have been lucky enough to have them in person almost every day for the last 4 years.

Sometimes when I get home Mary Kate asks "what do you talk about in the kitchen,"

I'd often answer with something like:

"Why bitcoin is the most important invention in human history."

"What is the true value of hard work"

"Real world Atlas Shrugged moments we've encountered."

"The thought that maybe money should be intrinsically valueless."

Then she just rolls her eyes and says "nevermind" when I answer. Boring to her, thrilling to us. She really just wanted to know if Brendan had been on any dates.

Summered up in a meme:

I'll definitely miss those deep philosophical discussions in the kitchen and cart.

I read this quote recently.

Wilbur Wright to Orville Wright shortly before his death: "Nearly everything that was done in our lives has been the result of conversations, suggestions, and discussion between us."

That's what my life has been so far and how I hope it ends.

Why Risk is Actually Staying Still

Lesson 3: The biggest risk isn't changing, it's staying still

Getting caught up in something you've grown out of and being too scared to change because you're comfortable and it's "good enough".

What if I never did this with my brother? Where would I be? I don't know the answer but what I do know is I like where I am and the person I've become. So based on that experiment change was the answer.

I will move forward with that assumption

To relate it to a common experience:

Can you remember that time you got dropped off at your dorm room for the first time?

A scary new territory but with endless possibilities that endlessly excite the mind. Soon you realize you didn't have to be scared. That's exactly how this transition feels, intimidating but with perpetual potential ahead.

The truth is, I never loved the core business function of Tuckedito. I loved the process optimization, the systems thinking, the big picture connections.

But I never wanted to be a chef or a restaurant owner. I just wanted to learn about business.

I spent years looking for permission from some mythical adult authority figure. Someone who would tell me it was okay to make big changes, okay to walk away from something that was working, okay to pursue what actually interested me.

That person doesn't exist.

This realization was liberating.

It meant I could stop waiting for permission and start making decisions based on what I actually wanted to do with my life.

That's what I plan to do.

There's Only Now

Lesson 4: You have the power to choose your own path

The past no longer exists, it's just a memory appearing in the now. The future doesn't exist yet, it's a dream appearing in the now. Life is just a series of nows.

Building Tuckedito taught me to choose my now as my career. I've always thought it but it's the first time choosing to live it.

4 months ago, I wrote down what I wanted my life to look like:

"I want to live a life that's honest, simple, and fully mine. I want to think for myself, keep my body and mind strong. I'll be a loyal husband, father, son, brother, and friend. I'll show up when I say I will. No pretending, no chasing things I don't need. I'll mess up. I'll change. But I'll stay open, ask better questions, and keep learning."

This transition to Simple Flo is me living these values, not just writing them down.

I will operate according to my personal values: don't get stuck, everything is here, life won't always be calm, creativity lives everywhere, and focus intently create value.

Anyway, I'm writing this partly to tell everyone my next step I guess, but mainly to capture my mindset at the intersection of a big change. So, that's part of why this is so excruciatingly long and more introspective than I intended it to be. It's a time capsule for my future self, or even my future kids if they ever think I'm cool enough to want to learn about what I used to be like.

I have a personal blog where I write and it feels closer to something that belongs there, I guess because I'm writing it for the same purpose as I write that.

Moving Forward: Simple Flo

My mission is to transform small business bottlenecks and chaos into systematic clarity through visual workflows and intelligent automations, saving 5+ hours weekly while creating scalable systems that grow with you.

I want to do this so small business owners and entrepreneurs can spend more time focusing on creating value for their community and building the life they want.

The thought of this business came years ago when solving my own problems. I wrote about it two years ago here. And have been honing and improving the idea since.

The idea that a simple flowchart + detailed instructions can save insane amounts of time and brain energy was a big one for me. I realized you can make your entire team's workflow visible, efficient, and collaborative with one tool.

Then around 8 months ago I started playing around with ai automations and realized I had to learn more. They pair perfectly with the visual work flows and are exactly what small business owners need.

With the combination of the two we can turn all that chaos into a simple visual map you can actually follow—like having GPS for your business. Plus smart automations handle the boring repetitive stuff automatically. Owners get their time back.

The business will run the same way as Tuckedito: I will always deliver what I say, on time, or your money back. Communication will be clear and honest.

The following video shows the end result of the service

Please pass along my contact info if you think this would be useful for anyone you know.

Reach out here: james@simpleflosolutions.com

Follow along here: newsletter - twitter - instagram

Can talk here: https://cal.com/james-pinder-simpleflo/floframe-express-discovery-call

Get a better idea of the business here: https://www.simpleflosolutions.com/

The Choice is Always Ours

There's no prescribed route, we don't have to do it the way everyone else says we should. We have the choice.

We are the author of our story. We choose the path. It's not about talent or luck—it's agency. It's the willingness to say "this is mine to solve" instead of "this is happening to me."

So after all that rambling time to get back to my feelings on wrapping up the business.

Bittersweet would be an awesome cliche for this feeling except I enjoy bitterness.

The feeling of wrapping up Tuckedito is sad and exciting. I know, not the 25 cent words I was taught at St. Stans but sometimes simple words work best.

Always sad to close a chapter of life that positively impacted me, but the unknown world of endless possibility is endlessly exciting. A wise man once said, "You gotta jump in to swim."

So, time to jump in again.