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Successful entrepreneurs love to credit "luck" for their success. In most cases, it's a humble deflection rather than the full truth.
Don't get me wrong, the great companies of the past century don't exist without luck. For every Google, there are hundreds of entrepreneurs who failed. But were those failed entrepreneurs simply victims of bad luck?
Not exactly. This is where "create your own luck" comes in. You generate fortune through relentless pursuit of a goal despite headwinds. Over a long enough timeline, consistent effort produces a few "lucky" bounces. But the create your own luck narrative has been overused.
Today, I want to talk about something more sinister: how young entrepreneurs actively sabotage their own luck.
Seneca wrote, "Luck is what happens when preparation meets opportunity." The problem? Most founders never give preparation and opportunity a chance to meet. They're too busy running around like a guillotined chicken.
Take DealBuilder, my last company. While we had unlucky moments, we were also incredible at making things hard for ourselves. We didn't just attempt one of the hardest business models to master (a software marketplace). We added:
A business valuation software
An online paid community for business owners
A software for franchise territory resales
A business brokerage
A SaaS tool for business brokers
We weren't throwing spaghetti at the wall, we threw the entire grocery store.
We eventually turned things around enough to manage a small exit to Deal Studio, but the following lesson stuck with me forever.
Picture this: every entrepreneur starts with a well. Some wells are deeper than others (born with better networks, more capital, or stronger skills). But everyone's well contains some water, representing your initial luck and advantages.
Okay, this is where this metaphor gets a bit gross but stay with me lol.
When you work hard, your sweat literally drips into the well. Early on, you're pulling up empty buckets. Frustrating and seemingly pointless. But here's what you can't see: every drop is accumulating at the bottom. With each bucket you lower, the water level starts to rise. You keep going. Then one day, your bucket breaks the surface and comes up full. Not because you finally got lucky, but because hundreds of empty buckets worth of effort finally reached the tipping point.
But here's the catch: you need to be drawing from one well. Our problem with DealBuilder? We were sprinting between five different wells. All that sweat equity wasn't falling into any single well. It was falling onto the ground between the wells, evaporating before it could compound into anything meaningful. A majority of successful entrepreneurs I’ve spoken to have fallen into this (lack of) concentration trap.
We can't control our starting position in life (how much water we start with) but we can control our effort and where we focus it. If you're hoping for better luck in 2026, take a moment to reflect on which wells deserve your time this year.
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The TL;DR? You focus on creating. Google AdSense handles the rest.
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idea of the week 💡
credit: ideabrowser.com
Problem: Freelancers face a brutal cycle. Invoice clears, rent hits, taxes loom, last month's slow period catches up—and suddenly there's nothing left to save. Good months vanish. Retirement stays a "someday" problem. W-2 workers have HR setting up 401(k)s and withholding taxes. Freelancers have a checking account and good intentions.
Idea: Pay Yourself First — an automated savings and retirement platform for freelancers. Connect your bank and invoicing tools (FreshBooks, Wave, HoneyBook). Every time a payment lands, money flows automatically into the right buckets: tax reserves, emergency fund, retirement. Flush month? More goes to long-term savings. Slow month? Minimums stay protected. No transfers to remember. No discipline required.
How it makes money: Subscription model at $19–49/month targeting freelancers earning $80K–$250K—enough income to save meaningfully, not enough to justify a $300/hour financial advisor. Start with automated savings and tax reserves, then expand into quarterly reminders, health insurance guidance, and investment recommendations shaped for irregular income.
Why it might win: Fifty-seven million Americans work for themselves now. The gig economy scaled, but the financial tools haven't. This answers the Reddit question asked every week: "How much should I be saving for taxes?" Grow through creator partnerships on YouTube and integrations with platforms freelancers already use. The pain is universal, the timing is perfect, and the market gap is massive.
friday fitness
at-home workout
Perfect for when you don't have access to a gym—just your body and some floor space.
Complete 5 rounds:
20 air squats
15 push-ups
12 reverse lunges (each leg)
30 mountain climbers (total)
20 bicycle crunches
Goal: Move continuously. Rest 30–45 seconds between rounds.
gym workout
A well-rounded session using basic gym equipment.
Complete 4 rounds:
12 dumbbell goblet squats
10 dumbbell bench press
12 dumbbell rows (each arm)
15 kettlebell swings
30-second plank hold
Goal: Challenge yourself with weight. Rest 60 seconds between rounds.
outdoor workout
For time:
400m run or brisk walk
20 push-ups (use a bench if needed)
30 jump squats
20 walking lunges (each leg)
200m sprint or fast uphill walk
Rest 2–3 minutes (until your heart rate settles), then repeat 2–3 rounds.
tweet of the week
The 2 word reply to an important email with ‘sent from iphone’ at the end is the greatest wealth flex in business
blog of the week
Selling to private equity can be the best outcome for many entrepreneurs, but you need to proceed carefully… as it could also be the worst decision of your life. This guide breaks down the common tactics PE buyers use during negotiations and the best defenses against them:
my plugs
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