Business

The Last Mile Is Where Success Is Made: Always Close The Loop

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, the opportunity slips away. As growth investors, it’s a reminder to take some profits 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 GBLX but can’t recall whether I made or lost money (probably lost).

Table of Contents

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! But also, no paycheck or 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, entrepreneur, 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 Still 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. Even though I’d make no money, it’s still a win-win.

This promotion ends May 10 and 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 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 that was it.

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. But I didn’t realize until the following Thursday morning 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 it my calendar.

When I finally responded and sent the calendar invite at 7 a.m. Thursday morning, 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. My bad!

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 a relationship.

But now? I average maybe one business-related meeting a week. I limit consulting to two sessions per month to protect my freedom and energy. That’s why you won’t even find my consulting page unless you search for it. If it were easily discoverable, my lifestyle would decline because demand is overwhelming.

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:

Check my calendar every morning
Set two alarms for every meeting: 30 minutes before and 5 minutes before

Why two alarms? Because I’ve missed meetings before 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, secure funding
Miss: Never launch
Result: No customers, no revenue

4. Writing a Book

Plan: Draft 90%, revise
Miss: Never reach out to agents, never get published
Result: Zero readers, zero impact

5. Investing

Plan: Do research, understand the risks and rewards
Miss: Never invest
Result: Money stays idle, slowing lagging behind inflation as your peers 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: Came 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 children, 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 here’s the truth: 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 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 client could have followed up too 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.

Millionaire Milestones book by Sam Dogen, Financial Samurai bestseller — Screenshot

Unfortunately, thanks to inflation, $3+ million is quickly becoming 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 wrote this book to help you achieve financial independence sooner, so you can live life on your terms. I hope you enjoy the read!

Intellectual Insider

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A blog which focuses on business, Networth, Technology, Entrepreneurship, Self Improvement, Celebrities, Top Lists, Travelling, Health, and lifestyle. A source that provides you with each and every top piece of information about the world. We cover various different topics.

Business

10 Charitable Organizations Entrepreneurs Should Support

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Opinions expressed by Entrepreneur contributors are their own.

From Tel Aviv to tech boardrooms, my entrepreneurial journey has taken me through building businesses, navigating painful failures, celebrating meaningful exits and eventually investing in other founders’ visions. I’m an Israeli immigrant who came to the U.S. with little more than ambition and a belief that hard work could move mountains. Over time, I’ve seen firsthand how startups are born from nothing but grit and vision — but as those companies grow, they begin to touch more than just market share. They influence culture. They inspire communities. And they bear the responsibility to give back.

In recent years, my focus has shifted from just building companies to helping others build theirs and, just as importantly, encouraging them to align their success with meaningful causes. After joining the Israeli-American Council (IAC) as a council member, I realized that beyond the business pitch decks and M&A spreadsheets lies something even more impactful: service. Through our initiatives supporting Jewish solidarity, educational programs and bridging relationships between American and Israeli entrepreneurs, I found that philanthropy isn’t just a “feel-good” endeavor — it’s a strategic advantage. It grounds founders, strengthens brand identity, builds community and invites purpose into what can sometimes feel like a grind.

So, here’s my call to fellow founders, startup CEOs and emerging entrepreneurs: Integrate charitable alignment into your DNA. Not for press. Not for optics. For impact.

Table of Contents

Make-A-Wish Foundation

Mission: Make-A-Wish creates life-changing wishes for children with critical illnesses, turning dreams into reality during their most difficult battles.

Startup life is full of “impossible” dreams — something Make-A-Wish embodies in a very human way. Supporting them isn’t just about giving; it’s about reminding your team what hope looks like. Tech company Atlassian has funded dozens of wishes through employee-led campaigns, showing how company culture can be both productive and profoundly kind.

Team Rubicon

Mission: Team Rubicon unites the skills and experiences of military veterans with first responders to rapidly deploy emergency response teams.

Startups are built on agility — and Team Rubicon is a masterclass in organized action under pressure. They’re a phenomenal organization to support, especially for founders with veteran ties or a passion for community disaster response. Their recent deployment to Maui after wildfires made national headlines.

Operation Gratitude

Mission: Operation Gratitude delivers care packages and personalized letters to deployed troops, veterans, wounded heroes and first responders.

Startups often talk about grit and sacrifice, and Operation Gratitude honors the Americans who live those values every day. Supporting this organization provides tangible appreciation to service members and can unify teams around shared patriotic values. It’s especially meaningful for companies with veteran employees or founders, or those wanting to show support for public servants.

The Trevor Project

Mission: The Trevor Project provides crisis intervention and suicide prevention services to LGBTQ+ youth.

Today’s workforce values inclusion, and The Trevor Project is on the frontlines of emotional and mental health. Their work intersects with DEI (Diversity, Equity and Inclusion) priorities that many startups strive for. Salesforce has championed LGBTQ+ causes through The Trevor Project, showing how social alignment can reflect core brand values.

Israeli-American Council (IAC)

Mission: The IAC builds an engaged and united Israeli-American community that strengthens the Israeli and Jewish identity, the American Jewish community and the bond between the people of the United States and Israel.

Beyond my personal affiliation, IAC offers incredible opportunities for founders to connect with global networks, Jewish and Israeli-American business leaders, and to support education, cultural diplomacy and solidarity during global crises. When Israel faced economic and emotional turmoil during recent conflicts, IAC quickly mobilized both humanitarian aid and business support.

DonorsChoose

Mission: DonorsChoose empowers public school teachers by funding their classroom projects, from books to science kits.

Education is the ultimate upstream investment. Many of today’s innovators were inspired by great teachers — yet those teachers often lack basic resources. Supporting DonorsChoose lets entrepreneurs impact students directly, and startups can align product donations, campaigns or even team volunteering around local classrooms.

Feeding America

Mission: Feeding America is the largest hunger-relief organization in the United States, providing meals through a network of food banks.

No one innovates well on an empty stomach. Hunger is closer than many founders realize, especially in cities with both tech hubs and underserved populations. Recent partnerships with companies like Amazon and General Mills show how even operational efficiencies (like surplus distribution) can be used for social good.

Girls Who Code

Mission: To close the gender gap in tech by equipping young women with the computing skills to pursue 21st-century careers.

Founders often talk about the pipeline problem — Girls Who Code solves it. Their alumni now work at Google, Meta and hundreds of other startups. Supporting them isn’t just charitable; it’s a strategic investment in a more balanced, innovative future.

Operation Underground Railroad (O.U.R.)

Mission: O.U.R. works to rescue children from sex trafficking and exploitation and partners with local law enforcement around the world.

Modern slavery is real — and profitable. It’s time for ethical businesses to help end it. O.U.R. gives companies a direct way to engage in awareness, funding and rescue missions. With ongoing cases in Central America and Southeast Asia, their work is urgent and impactful.

St. Jude Children’s Research Hospital

Mission: St. Jude leads the way the world understands, treats and defeats childhood cancer and other life-threatening diseases.

St. Jude combines compassion with cutting-edge research — a formula every biotech or health-tech founder should admire. What sets them apart is that families never receive a bill. Startups can support them through percentage-of-revenue donations, corporate sponsorships or employee matching programs.

Startups are inherently optimistic. They are born from belief. But belief without action is hollow. These ten organizations aren’t just charity checkboxes. They’re powerful channels for meaning, connection and responsibility. When founders integrate giving into their companies, they don’t just enrich the world — they enrich their teams, their culture and themselves.

As someone who has gone from bootstrap to boardroom, from failure to fortune and from founder to funder — I can tell you this: Success that stands alone feels empty. But when your company becomes a vehicle for change, everything you build starts to matter more.

So, the next time you pitch your business, ask yourself: What are you building it for?

Intellectual Insider

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Business

When You Don’t Want Your Kids To Be Just Like You

There comes a moment when your child might look up and say, with wide-eyed innocence:

“I want to go to the office and type on a laptop all day like Mommy.”
“I want to travel abroad for work for two weeks at a time like Daddy.”
“I want to have video meetings at home and in the office like you.”
“I want to go to work and come home late at night every day like Daddy.”

At first, you may feel a surge of pride. Your hard work is being seen. You’ve become a role model. But almost as quickly, that pride can twist into something else: concern.

Because if they truly knew what it was like to be you—stressed, exhausted, chasing financial security—they might rethink their dreams. And you might, too.

Why I Don’t Want My Kids to Be Like Me

After publishing Buy This, Not That, I was drained. Traditional publishing was new for me, and while I was proud to try it, it felt like swinging two bats at the plate—exhausting but satisfying to let go.

Then my publisher offered me a two-book deal. I hesitated. Did I really want to put myself through the grind again? Part of me said no. But another part—the part that wants to instill a strong work ethic in my children—said yes.

As a FIRE parent, I worry about raising entitled kids who don’t appreciate how hard life can be. So I committed to the second book, not just to help readers, but to show my kids what persistence looks like.

The Second Book, And A Moment Of Dread

Two and a half years later, Millionaire Milestones: Simple Steps To Seven Figures is finished and will hit shelves on May 6, 2025. My son has seen me write, heard me talk through chapters, and even weighed in on cover designs.

One day after school, he told me, “I want to be a writer like you, Daddy.”

My heart swelled. And then sank.

Because while writing is rewarding, it’s also brutally hard and not financially practical for most.

The Arduous Life of a Writer

I’ve often wondered how kids end up pursuing some of the least lucrative jobs after 17 years of education. Don’t they realize the world is too cruel to let them major in Art History, English, or Poetry?

Maybe not. In school, they’re encouraged to be creative, follow their passions, and believe they can achieve anything with hard work.

Unfortunately, life has bills to pay.

Unless you’re from one of the wealthiest families, spending four years and hundreds of thousands of dollars on college to pursue a career in the arts is impractical.

If my son majored in English and became a writer like me, he’d face many hungry days. He’d likely never earn enough to buy a home, let alone get married and start a family.

Instead, he could end up living in our garage, wondering where it all went wrong. During my 24 years in San Francisco, I’ve seen plenty of adult sons living at home, unable to provide for themselves.

My wife and I might not see grandchildren either. By pursuing writing, our family lineage could end, unless we build a genetic dynasty like the one in Isaac Asimov’s Foundation.

The Harsh Economics of Writing

The average book advance? $5,000–$10,000. Even a top 1% advance of $250,000 is usually split over 3–4 payments and 2–3 years. That’s maybe $83,000 a year, hardly a golden ticket, especially in a high-cost city.

And most writers don’t even get a deal. Roughly 95% fail to land one. The odds are long. The income is low. Don’t become a professional writer if you want to live well.

As one dad said to me in 2022, when I mentioned writing another book, “I’m sorry. Artificial intelligence is disrupting everything.”

So when my son says he wants to follow in my footsteps, I feel conflicted. I want him to be creative and fulfilled. But I also want him to eat.

Blogging Isn’t Easy Either

“Can’t he just start a blog like you did?” some might ask.

Sure. But most bloggers make little to nothing for years, even if they publish three times a week. AI-generated content is flooding the internet, but it’s not winning reader trust or SEO rewards, yet.

Yes, he could try YouTube or podcasting. But those, too, are long games filled with uncertainty.

Don’t build your main career on a platform you don’t own, and don’t expect passion alone to pay the bills. Here are some more reflections on making money online since 2009.

Meaningful vs. Lucrative Careers

Ideally, your child will find work that’s both meaningful and financially secure. Doctors, nurses, and teachers all contribute to society in incredible ways. But even they face burnout. For teachers, they often aren’t paid enough for what they do.

On the other end are the high-paying but potentially soul-draining jobs—investment banking, big tech, management consulting, and law—the industries where many elite university graduates land. While the work may not be fulfilling, these roles can accelerate the path to financial independence.”

Demand for software developers is declining — Even the once-coveted software developer job may be getting disrupted by AI.

The Freedom To Choose Comes From Financial Stability

If my son wants to write, I hope he does it as a side hustle, at least until he’s financially stable.

Personally, I’d love for him to pursue a career that helps society, even if it doesn’t pay well. But he’ll only have that choice if he builds wealth early. Passion without income is a fast track to resentment.

Before you try to save the world, you’ve got to save yourself.

Work Ethic Is The One Thing You Can Control

You can’t dictate your child’s path, but you can model determination, discipline, and pride in your work. Those are universal skills in any field.

That’s one reason I pushed through writing Millionaire Milestones. It’s not just a book, it’s the culmination of decades of financial learning, packaged to help people build great wealth step-by-step. Further, it’s an example of work ethic.

But let’s be frank: there’s no way I could have written this book or maintained this site without the net worth and passive income to support my family.

Writing is a labor of love. It brings deep satisfaction. But the freedom to do it regularly came only after financial independence.

Final Thoughts

So when your kid says they want to be just like you, take a moment. Smile. Hug them. Then think hard about what it means and what kind of life you really want them to have.

Because maybe the greatest gift we can give our children isn’t just inspiration. It’s optionality.

Millionaire Milestones is out tomorrow and I’d love for you to pick up a hard copy. Thank you for your support!

Millionaire Milestones book by Sam Dogen, When You Don’t Want Your Kids To Grow Up To Be Just Like You — Click the link to pick up a copy on Amazon

Reader Questions

Readers, do you believe in following your passion or being practical? Do you want your kids to grow up to do what you do? Why or why not? How do we ensure our kids choose occupations that pay enough and are also spiritually rewarding? How do we instill in our children a work ethic that will help them succeed, no matter their occupation?

When You Don’t Want Your Kids To Grow Up To Be Like You is a Financial Samurai original post. All rights reserved. For more personal finance insights, join 60,000+ others and sign up for my free weekly newsletter.

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Business

Learn How to Delegate Now — or Risk Losing Your Business

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Opinions expressed by Entrepreneur contributors are their own.

Successful entrepreneurs often share similar qualities — they’re driven, resourceful and ready to wear multiple hats to turn their vision into a reality. In the early stages of building a business, being a jack-of-all-trades isn’t just an advantage; it’s a necessity.

Given the nature of the job, it can be challenging for entrepreneurs to learn how to delegate effectively as a company grows — but it’s one of the most important skills to master for scaling a business and sustaining long-term success. The ability to recognize when to seek help, which tasks to delegate and how to lean on the expertise of others is what separates thriving businesses from those stuck in survival mode.

For me, the delegation lesson came early on in my entrepreneurial journey when I found my startup at a critical crossroads. In the beginning, I was operating as a one-man show, offering my software for free while personally handling support inquiries from our 500 users when I wasn’t at my full-time job. It quickly became clear that it wasn’t sustainable to continue managing this on my own, and I was faced with the choice of either eliminating support completely or finding a way to share the workload.

I decided to hire my very first employee to manage the increasing volume of support requests so I could focus on further expanding our user base and building a sustainable business model. By delegating support, my business was able to scale significantly without sacrificing the high-quality customer service that continues to define our brand today.

Table of Contents

Breaking the “it’s easier to do it myself” mindset

If you don’t learn to delegate, your business growth will always be limited by your own capacity and capabilities. Handling everything on your own may feel efficient in the moment, but in reality, it restricts your potential as a leader and as a business. You only know what you know, and there are only so many hours in the day. Imagine what you and your business could be capable of if you had the right support from the right experts.

A solo mentality often leads to burnout, missed opportunities and stagnation. Shifting toward a leadership mindset doesn’t necessarily mean letting go of control — it’s about maximizing your impact. By trusting and empowering others, you’ll free up valuable time to focus on strategy, innovation and the big picture, ultimately driving greater success.

Start small and start now

If delegating isn’t your strong suit, the most effective way to build the habit is to start small and start now. Pick a task from your list — no matter how small or important — and delegate it to someone else on your team. Then move on to the next task and the next. The more you delegate, the more you’ll lighten your workload while building confidence in your team and their abilities. Over time, delegating will come more naturally, and you will encourage those around you to step up and excel.

Progress over perfection

In the beginning, tasks may not be done exactly as you would do them yourself — and that’s okay. Focus on progress over perfection. Effective delegation will be a learning process for both you and your team, requiring some patience, communication and trust. Instead of micromanaging or taking tasks back at the first sign of imperfection, try to embrace these moments as teaching and growth opportunities.

Building a stronger, more capable team

Delegation is a powerful tool to help your team grow. By entrusting your team with meaningful tasks and encouraging problem-solving and accountability, you’re creating a culture where employees can develop new skills and build confidence in their abilities. When your team feels empowered to solve problems and make decisions, they are more likely to feel a sense of ownership and pride in their work. This sense of responsibility fuels engagement, motivation and investment in the success of the business.

Over time, delegation will only strengthen your team to become more self-sufficient and capable. As they take on more responsibility and grow in their roles, your business becomes more resilient with a stronger foundation. This growth enables you to scale your business efficiently without sacrificing the quality that is critical for long-term success.

Practical steps to delegate effectively

Choose what to delegate: Reflect on your workload and identify the tasks that truly require your direct involvement and those that don’t. Time to be honest about your strengths and weaknesses — does someone else on your team have the expertise to handle certain tasks more efficiently? Consider the time-consuming or repetitive tasks you could delegate to free up your time for higher-priority work.
Pick the right person: Be intentional about assigning the right tasks to the right individuals based on their skills and experience. Think about those who are capable, eager to learn and show the most growth potential.
Set clear expectations: Clearly define the scope of the task at hand, outlining key deadlines, objectives and your desired end result to set your team up for success. Provide any necessary resources or background context, and be available to answer questions or offer support along the way.
Support without controlling: Trust is the key to effective delegation — which is why it can be such a tough skill to master. Resist the urge to micromanage or demand perfection. Give your employees room and autonomy to complete the task in their own way while you remain accessible for guidance and support if needed.
Follow up and offer feedback: Schedule deadlines or check-ins to review progress and provide constructive feedback. Prioritize recognizing successes as highly as addressing any challenges.