10 Counterintuitive Lessons from a Decade-Long Journey as a Small-Town Founder
Cheers to 10 years with Codefi! Celebrating the journey to $20 million for an innovation economy
I come from a lower-middle class family. Small town. No college degree. Instead of following a road well-traveled, I decided to go down an unconventional path.
(~14 min read)
Last week, Codefi passed the 10-year mark. We also surpassed $20 million in total fundraising (with a third yet to be deployed) which will have significant economic impact in the coming years. These milestones led me to reflect on the journey and lessons learned along the way.
I have increasingly been more curious about how people and organizations truly succeed, especially in ambiguous environments. What unique experiences molded them? So this is for those who share that curiosity. I've narrowed it down to 10 counterintuitive lessons that have been formidable for me as a founder over the past decade. I definitely welcome if you'd like to share the most insightful wisdom gained in your own journey.
1. Manifestations and Suicide
In my late teenage years into my early twenties, I was hooked by self-improvement books and experts. Think and Grow Rich by Napoleon Hill instilled in me that I was the master of my fate and captain of my soul. If I internalized events, had goal-setting techniques, increased productivity systems, followed intense workout and diet regimens, and truly believed when I said self-affirmations, then I could be like whoever my mind aspired to be and achieve whatever my heart desired.
While I attribute parts of my growth to those practices, the "hustle and hack culture" can go too far—especially when the pursuit of self-optimization consumes someone's identity. They may feel untouchable—even invincible—but life has a way of grounding even our most intense pursuits.
During the time I was launching my first company, my mother attempted suicide several times. A month before starting Codefi, my then-girlfriend also tried to end her life. I had worked so incredibly hard to manifest a new life for myself, but sometimes unimaginable challenges have kicked me in the teeth. As much as I felt I could control fate, I am still human.
I want others to know that how you feel—or react—during these moments doesn't necessarily define you. As powerful as we may feel or appear, we’re all vulnerable to the unexpected. I've shared my full story before, and I feel a deep responsibility to help make mental health an accessible and open topic in everyday conversations because these struggles deserve acknowledgment as much as our achievements.
(Most importantly: 988 Lifeline | Call - tel:+988 | Text - sms:988 | Chat
Secondly, I welcome you to refer a friend to this post if you think they may potentially benefit from reading this section in particular.)
2. Let Some Fires Burn
I learned that when there are too many fires to reasonably put out, it's easy to lose focus, become less effective, or even feel immobilized—the art has been to distinguish between those that could safely smolder and those that could potentially burn everything down. Founder of LinkedIn, Reid Hoffman, illustrated this brilliantly in Blitzscaling: when overwhelmed with calls in their early days, they didn't hire more customer support representatives—instead, they removed their phone number entirely from their website.
Over time, I've developed my own prioritization method through testing, trial and error. I combine multiple approaches:
The ABC123 method for importance and priority ranking
Kanban for workflow visualization and deadlines
Scrum's Fibonacci Sequence for complexity estimation and measuring productivity
There are many different ways to manage time, planning, and what to do. The goal isn't to extinguish every fire, but to focus resources where they matter most. If you've discovered effective approaches for handling competing priorities when everything seems urgent, please share.
3. On Deciding Less
Making constant decisions—especially during intense periods—can be mentally depleting and cloud judgment. To combat this, I've ruthlessly simplified some of the most mundane recurring events. The objective is to combat Decision Fatigue. This is a state of mental exhaustion that can impede a person's ability to continue making decisions after a period of the sheer number or time committed to making decisions causes an overload.
My approach includes keeping multiples of the same pants, shirts, and shoes, maintaining the same breakfast and lunch, and following a consistent morning routine. People are probably most familiar with Steve Jobs and his black turtle neck, blue jeans, and sneakers. These things may seem unnecessary or extreme to some, but it's necessary for me.
Through the years, I've been refining a decision-making framework that essentially helps with being most effective through ambiguous environments. The framework, questions, and measurements can be used at levels from individuals to projects to programs. So, more than just materialistic things and events, I'm hopeful to eventually share these concepts if they may be helpful to others.
As Nobel Prize winner Daniel Kahneman discusses in Thinking, Fast and Slow, our minds can only handle so many choices before fatigue sets in. By eliminating minor choice points, I conserve my mental capacity for decisions that truly impact critical outcomes.
4. Mental Palette Cleansing
During a 2018 fireside chat, Gabe Lozano, CEO of LaunchCode, described what was a rarely discussed founder challenge at the time—context switching: diving deep into analytics one moment, rising to high-level strategy discussions with executives the next, then suddenly handling delicate HR situations.
These rapid shifts between different levels of thinking are a subtle but crucial skill to master. I’ve personally found a transition technique: "mental palette cleansing." This concept is the method of hyperfocus interspersed with intentional mental resets, which has helped with clarity and effectiveness while serial tasking.
While traditional time management techniques like Pomodoro or Time Blocking focus on structure, they often miss a critical element: the transitions between tasks. These approaches, while seemingly helpful, don't align with how our brains naturally prefer to work. They rely on fixed schedules, which are actually the least effective reinforcement strategies for sustained focus according to behavioral psychology.
I've found that variable-interval scheduling with positive reinforcement works best: giving complete attention to the current meeting or task, then using transitions as intentional rewards—using moments for activities others might see as distractions. For me, it must be a mentally stimulating activity to actually enhance the switch to the next task: playing a quick game, exploring specific subreddits, or having a conversation with the latest LLM voice.
5. Rethinking Absolutes
I've come to realize that there are far fewer absolutes than I once thought. My understanding of absolutes began with my views on work ethic: I grew up believing hard work would always beat both knowledge or talent that was poorly executed, and that without hard work, success was impossible. This evolved into its opposite: always work smarter, not harder, because brute force could never compete with adaptability. Then I swung further: optimizing both simultaneously at all costs, which seemed like the only strategy to reach new heights.
Now, I see the limitations of these absolutes. I’ve learned to weigh effort versus effectiveness, to recognize diminishing returns, to avoid overengineering, and to appreciate the role of serendipity. A pattern emerged: statements containing "always" or "never" often revealed themselves as oversimplifications that required necessary corrections in my thinking.
Rather fitting: "Never say never" and "It will always be that way... until it isn't." There are rarely absolutes.
6. Fallibilism
I've always had a pursuit of certainty and desire for perfectionism. It eventually led me to Judea Pearl's The Book of Why, which transformed my understanding of causality and truth. His observations sparked a profound shift in my thinking:
You cannot answer a question that you cannot ask, and you cannot ask a question that you have no words for.
This search for better questions, rather than absolute answers, also led me to discovering fallibilism through David Deutsch's The Beginning of Infinity, which holds that “propositions can be accepted even though they cannot be conclusively proven or justified, or that neither knowledge nor belief is certain." Leaning into fallibilism, I've learned to "battle test" my thinking by deliberately creating the strongest possible case against my own ideas and beliefs—a practice known as Steel Manning.
Adopting this mindset has refined my ability to ask better questions, leading to deeper understanding and more meaningful solutions. Such a perspective helps view problems not as failures but as inevitable yet essential steps for growth. Startup culture often sensationalizes stories to the point where it feels like "failure porn". The true lessons aren't in glorifying the fall but in developing how to better learn to analyze, adapt, and advance from these moments.
In the pursuit of continual progress, this approach has encouraged me when I've needed to accept being approximately right rather than precisely wrong.
7. Beyond Resilience
Building a company requires constant evolution. I thought Ben Horowitz captured this perfectly for leaders in The Hard Thing About Hard Things when he emphasized that a founder’s learning curve must accelerate to stay ahead of their company's growth. That in and of itself was a great practical insight.
This concept of necessary adaptation led me to Nassim Nicholas Taleb's more theoretical approach in Antifragile:
Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.
I've observed this principle at multiple levels—from individual founders to entire communities. The key is understanding how risk and response both can cascade through different layers: what stresses one part of a system may strengthen the whole. Most I've worked with have talked about avoiding weaknesses, creating strengths, or building resilience. Few considered the advantages from efforts of intentional disruption that could lead to increased capabilities to thrive.
The startup and tech industries have experienced major changes, shocks, and volatility the past few years: covid-19, a booming economy for tech workers and large increases in startup funding, followed by massive layoffs and major constrictions, and the now increasing speeds of artificial intelligence capabilities. Economic environments like what we are in right now are typically when the most successful companies have historically launched.
Like a muscle that strengthens under stress, the right kind of challenge at the right level can transform potential breaking points into breakthrough moments.
8. Why 10x Growth can be Easier than 5x
Ash Maurya has discussed a counterintuitive insight: growing 10x can paradoxically be easier than growing 5x. Whether setting much larger goals or significantly shorter deadlines, both force a rethinking of entire paths forward. I've learned that setting audacious goals often demands simplification, which can spark innovative solutions that modest targets rarely inspire.
Tim Ferriss echoes this principle in The 4-Hour Workweek, noting that:
Skills are overrated. Perfect products delivered past the deadline kill companies faster than decent products delivered on time.
This mindset of radical acceleration has practical applications: I've witnessed how adding firm deadlines to ambiguous objectives forces focus, while experimenting with achieving deadlines in half the time—or even just 10% of the time—reveals inefficiencies and promotes decisive action. It's ironic how implementing just one of these approaches can automatically resolve many decisions that previously lacked direction.
These exercises pair well with Prioritization because they bring unresolved decisions to light and cut through ambiguity, helping focus on what truly matters when aiming for exponential growth over incremental improvements.
9. The Perfect Enemy
I've sometimes gone down philosophical rabbit holes, spending days or even weeks grappling with questions like, "Am I doing things right?" and "Am I doing the right things?" This can quickly spiral into "What is the purpose?" then "What is my purpose?" They have often led to existential conversations with Socrates, Plato, or Aristotle... "Why is there... purpose?"
Through this journey, I've seen where perfectionism can come from deeply rooted fears masquerading as rational thought. I still wrestle with some of these questions, but comedian Mike Birbiglia offers breakthrough guidance:
You can't make each night a referendum on whether or not you should be doing what you're doing. You just have to do it a bunch.
In On Writing Well, William Zinsser offered clear wisdom with his idea that "simplicity is the ultimate sophistication." This resonated deeply: clarity often comes not from adding complexity, but from distilling ideas to their essential truth.
One technique I've found helpful is to simply become aware of how you think and make decisions: first by a quick 5-minute writing exercise to describe a situation, identify the specific fear or distortion, then examine what you may believe are the the underlying beliefs, and finally describing the resulting behavior (what you actually did). This systematic approach—combined with increased mindfulness and self-awareness—has helped me recognize when I'm letting perfect become the enemy of progress.
10. Letting Go
There have been times where letting go is difficult because of a sunk cost fallacy, loss aversion, or a fear of regret. There have been attachment and nostalgia biases. What makes this lesson peculiar for me personally is there is no "desire for control."
In Ask Your Developer, Twilio co-founder Jeff Lawson shares insights from Eric Ries:
Innovation is like planting seeds in the ground. You don't necessarily know which ones, if any, will grow into giant trees. But you do know one thing: if you don't plant any seeds, you won't get any trees.
Collectively, I think we need to plant more seeds.
I have learned that sometimes the hands that have helped build and grow something must eventually release their grip. Having such cherished relationships makes this lesson the hardest.
Yet paradoxically, from this distance and vantage point, I will gain a new perspective and deeper appreciation for something remarkable: the evolution from what we've built together to what they will build next.
Build Better Things Together
I'm curious; do any of these resonate most with your experiences? What's the most counterintuitive insight you've discovered on your own journey?
To everyone who has cheered, supported, contributed, or been impacted by Codefi: thank you. As always, Codefi is just getting started. Now, let’s get to work!
This article would be 10 pages long if I listed everyone I owe this milestone to, but one deserves special gratitude:
James Stapleton, PhD - thank you for taking a counterintuitive bet on me.
Sources & Further Reading
I am not an affiliate marketer, nor is there any financial incentive for providing the information below. I am strictly sharing links to hopefully be helpful for anyone interested themselves.
Books & References:
988 Lifeline | Call - tel:+988 | Text - sms:988 | Chat
10 Best Online Therapy Services in 2024 by Sarah Davis (Forbes)
Think and Grow Rich by Napoleon Hill
Questioning Rural by Chris Carnell
Gabe Lozano, CEO of LaunchCode
Ash Maurya, founder of LEANSTACK and author of Running Lean
Eric Ries, author of The Lean Startup and Founder of LTSE
Key Concepts
ABC123 - time management system built upon from Alan Lakein's prioritization principles.
Kanban, Scrum, and Fibonacci Sequence - agile project management methodologies emphasizing visualization, iterative progress, and complexity estimation.
Fallibilism - philosophical approach to knowledge, recognizing the inherent uncertainty in all beliefs.
Steel Manning - advanced form of argumentations, involving building the strongest possible version of opposing viewpoints.
Partners & Startups
I'd like to give a special thank you to 10 major #EconomicDevelopment partners:
Center on Rural Innovation–advancing digital economy ecosystems in rural communities.
Delta Regional Authority–supporting economic development in the Delta region.
U.S. Economic Development Administration–funding and supporting regional development.
efactory–fostering innovation and entrepreneurship in Missouri.
Missouri Department of Economic Development–driving economic opportunities across Missouri.
Missouri Department of Higher Education & Workforce Development–building a skilled workforce for the state.
Missouri Technology Corporation–investing in technology and startups in Missouri.
The Bank of Missouri–providing financial support for local business growth.
U.S. Department of Labor–supporting job growth and workforce development.
U.S. Small Business Administration–empowering small businesses through funding and resources.
I'd like to give special recognition to 10 #startups (some now grown up) we've had the pleasure to work with closely:
Coangler–connecting anglers to the best fishing experiences.
Concept AgriTek–innovating sustainable agriculture solutions.
Parent ProTech–simplifying tech for parents and families.
PubGen–transforming publishing and content creation.
PumpTrakr–improving efficiency in irrigation management.
Sho.ai–empowering brands with AI-driven solutions.
Swipesum–streamlining payment processing for businesses.
upSwot–providing real-time analytics for small businesses.
Vendoor–real-time updates for job sites and their vendors.
Venku–connecting people to outdoor adventures.
#StartupLife #Innovation #Entrepreneurship #Technology #Leadership #FounderJourney #TechStartups #CodefiTurns10