In 1997, Gary Winnick founded Global Crossing, a company with the bold vision of laying undersea fiber-optic cables to build a global IP-based telecommunications network. It was a massive infrastructure play, designed to form the core transport layer for the internet, connecting data centers and network hubs worldwide.
But as visionary as the plan was, none of it mattered without one crucial component: the last mile. That final connection to consumers and businesses determined whether the network could fulfill its promise.
Global Crossing became one of the most hyped companies during the dot-com boom, peaking at a $47 billion market capitalization. The demand for internet bandwidth surged – just as predicted. But by 2001, the bubble burst. The company had overbuilt its capacity and couldn’t generate enough revenue to cover its debts. In January 2002, it filed for bankruptcy with $12.4 billion in liabilities.
The lesson? You can be early and even right, but if you don’t complete the journey at the right time, the opportunity slips away. As growth investors, it’s a reminder to take some profits from time to time when excitement runs high. Not every rocket ship reaches the moon.
Ah, those were the days. I was trading tech and internet stocks on the 49th floor of 1 New York Plaza like a man possessed. Such a career-limiting move in retrospect! I even traded GBLC but can’t recall whether I made or lost money (probably lost because day trading seldom works out).
Why Completing the Last Mile Is Everything
If there’s one mantra my wife is tired of hearing, it’s this: Finish the last mile. Looking back, I didn’t fully appreciate how much Global Crossing’s rise and fall shaped the way I operate today.
When you no longer have a steady paycheck—as I haven’t since leaving my finance job in 2012—there’s no one to catch you if you slip. No meetings? Fantastic! Forget to follow up? Oh well. But also, no paycheck and no accomplishment. Everything depends on your ability to follow through.
In contrast, as an employee, you could take two weeks off and still get paid. At large companies, your absence might barely register if you take a three-month sabbatical. But when you're on your own—whether as a retiree or solopreneur—the last mile is all on you.
Without finishing the final leg, all the planning, effort, and setup amounts to nothing.
A Recent Missed Last Mile That Bothers Me
I’m sharing this story because I dropped the ball, and I want to be accountable.
As part of promoting Millionaire Milestones: Simple Steps To Seven Figures, I offered readers a unique chance for a 1-on-1 financial consultation. The promotion: buy 55 hard copies at a bulk discount, which would total roughly 40% less than my normal consulting rate, and in return, get a personalized session. Clients could gift the books, and I’d get to help someone directly and spread the word. Even though I'd make no money, it's still a win-win.
This promotion ends May 10 and probably won’t return until my next book drops in late 2027 or mid-2028. If you're interested, you can fill out the short form at the end of this page.
One prospective client accepted the offer. We exchanged emails, and he filled out the onboarding questionnaire. I reviewed his info, and he proposed a date and time. I mentally confirmed, opened my calendar, created a Google Meet invite, wrote a note about looking forward to the call… and pressed save.
Unfortunately, I forgot to actually send the calendar invite!
Off we went on a five-night Tahoe ski trip. I even took a few consulting calls during downtime and returned feeling recharged. It's crunch time! But I didn’t realize until the following Thursday morning, four days after we had returned, that I had never confirmed the meeting with him.
There was no email, no invite sent. Just silence on my end, with the belief I had a call lined up all along as it was in my calendar.
When I finally responded and sent the calendar invite at 7 a.m. Thursday morning, the day of the supposed meeting, it was too late. His day had filled up. Worse, his last email to me was 11 days ago. Imagine paying for 55 books and then hearing nothing in return. I felt terrible.
Why I’m Now Bad at Meetings (And What I’m Doing About It)
In my finance days (1999–2012), meetings were everything. When helping IPO candidates pitch to clients, I’d sometimes attend 7–8 meetings in a single day. Being punctual and prepared wasn’t optional, it was expected. I'd also often meet with clients for meals or drinks. There was no way I could ghost them if I wanted to build good relationships.
But now? I average maybe one business-related meeting a week. I limit consulting to one or two sessions per month to maintain my freedom. That’s why you won’t find my consulting page unless you search for it. The demand is overwhelming, and taking it on would recreate a full-time job, causing my lifestyle to decline.
The result? My “meeting muscle” has atrophied. Sometimes I forget appointments that are in my calendar. Alerts pop up, and I’ll still mentally dismiss them, as if they were invisible. Since 2012, my brain has been rewired to operate on my schedule, not someone else’s.
So here’s what I’ve started doing since early 2025:
- Check my calendar every morning
- Set two alarms for every meeting: 30 minutes before and 5 minutes before
Why two alarms? Because I’ve still missed meetings in the past after the 30-minute one goes off. Oh boy… the rewiring for meetings takes time.
Success Comes From Closing the Loop
You can brainstorm, plan, and prepare endlessly, but if you don’t complete the final step, none of it matters. The last mile is where results happen. Here are some common examples:
1. Job Hunting
Plan: Build a resume, research companies
Miss: Never apply or skip interviews out of fear
Result: No job, no progress, no money
2. Fitness Goals
Plan: Buy gear, get a trainer
Miss: Don’t go consistently
Result: No transformation
3. Starting a Business
Plan: Build a site, come up with an idea
Miss: Never launch
Result: No customers, no revenue, no breaking free from from a job you dislike
4. Writing a Book
Plan: Draft 90%, revise
Miss: Never reach out to agents, never get published
Result: Zero readers, zero impact, no legacy left
5. Investing
Plan: Do research, understand the risks and rewards
Miss: Never invest
Result: Money stays idle, slowing lagging behind inflation as your peers who took risks get richer
6. Education
Plan: Pass exams, attend class when you're not hungover
Miss: Only attend for three years and drop out to start a band
Result: No degree and $60,000 of student loan debt
7. Relationships
Plan: Come up with a witty opening line to reach out
Miss: Never call, meet up, or send the message
Result: Missed connection, no joy, no love, no family, only more loneliness
8. Financial Planning
Plan: Create strategy, hire a financial professional, or take advantage of my promotion
Miss: Don’t implement
Result: Great plan, no results, and being filled with regret when you're 65
The Finish Line Is Where the Magic Happens
We all know people who start with incredible energy but never follow through. I’ve been guilty of that more times than I’d like to admit. But the real value, the growth, the reward—it all lives in the last mile.
Whether you're building a business, planning for retirement, or simply trying to keep your promises: finish the last mile. The world rewards follow-through.
Readers, are there things you’ve started but didn’t complete that crucial last mile? If so, what held you back?
Sometimes, not finishing is a sign it’s time to move on—and quitting can actually be the smarter choice if progress has stalled. Do you have any examples where walking away turned out to be the better decision?
A realization after the fact: After a 10-minute sit-down with my wife at the dining table, she helped me realize a couple of things. First, the prospective client I forgot to send the invite to had never actually ordered the 55 books—which is huge! That made me feel a lot less bad about forgetting to send the calendar invite. Second, the prospective client could have followed up after several days. Communication goes both ways.
Order A Copy Of Millionaire Milestones Today
Huge thanks to everyone who’s pre-ordered a hard copy of Millionaire Milestones: Simple Steps to Seven Figures so far. From what I see, Amazon currently offers the best price with a lowest price guarantee.
This book is my attempt at writing a modern-day version of the classic The Millionaire Next Door. Times have changed, and so have the many different ways to achieve millionaire status.
Unfortunately, thanks to inflation, $3+ million is the new $1 million—and by the end of this decade, $5 million might take that title. Without proper saving, investing, and calculated risk-taking, building outsized wealth is only getting harder.
Lucky for us, we have the knowledge and resources to outperform. I hope you enjoy the read!
This post really hits home. The ‘last mile’ concept is such a powerful metaphor—not just in business, but in relationships, parenting, and personal growth.
It’s amazing how often success hinges not on brilliance, but on consistency and follow-through. I’ve definitely dropped the ball before by assuming the hard part was over, only to realize I missed a crucial final step. Thanks for the reminder that excellence lives in the details, especially at the end.
PS, I agree with your wife. Communication is a two-way street. Always follow up after several days if you haven’t heard back and find the topic important.
-through being more important than brilliance—so true. It’s often the unglamorous, persistent effort at the end that separates good from great. And yes, the reminder to close the loop in communication really stuck with me too. It’s easy to assume silence means disinterest, but often it’s just life getting in the way. Following up shows care and intent. Appreciate your insights!
I am very guilty of not completing things especially the non essential tasks on my to do list. If I have a clear deadline, I’ll for sure hit it. But if I can get away with procrastination I tend to delay starting or start but delay the finish usually because I get distracted with something else or reshuffle priorities. It’s a long time bad habit.
This reminds me of one particular thing that’s been on my to do list. I realized six months after getting new frames and lenses that I can submit an insurance claim for partial reimbursement. But I also learned I have up to 12 months from the date of service to submit the claim.
So did I keep the momentum going and actually execute on filing a claim? Nope. And here I am 10.5 months after date of service, and just 1.5 months before my chance expires for good, still skipping over it on my to do list. I’ve put it off because it’s a pita to fill out the paperwork and make copies, but really I just don’t want to do it lol.
But shifting my mindset to me essentially throwing money away by not getting it done, has convinced me to put it at #2 on my to do list today. I’ll hold myself accountable now that I’ve put it out there in the world!
Totally relatable—and I appreciate the honesty! It’s funny how we’ll put off a task for months, even when it’s basically like leaving free money on the table. I’ve definitely had similar moments where the mental cost of procrastination ends up outweighing the actual task. Good on you for reframing it as throwing money away—that’s a great motivator. Now that you’ve made it public, you’ve got the accountability boost too. Rooting for you to get that claim in with time to spare!
I’ve known a lot of people who give up after the first mile. Usually, it’s because they’re distracted by something new and their original idea is never incubated properly. Enthusiasm is not enough. Determination must be right behind it.
I think hard-driving people have the opposite problem: not knowing when to quit. They do three miles past the end of the marathon, keep putting effort into relationships that should be left to natural causes and (worst of all) stay in jobs they should’ve left years ago.
That’s a great observation—both quitting too early and holding on too long are traps on opposite ends of the spectrum. It really highlights how success isn’t just about grit, but also about discernment.
Knowing when to push through and when to pivot or let go is a rare skill, and I think it often only comes with experience (and a few stumbles). The challenge is figuring out whether we’re running the right race in the first place.
In FIRE land, the biggest thing I see is people suffering from the one more year syndrome, where they just can’t let go of their day job to do something else, even though they have enough money.