Be Your Best Boss

Reinvent Yourself from Employee to Entrepreneur

William R. Seagraves



Foreword: Perry Marshall


Part I: Are You Ready for a New Boss?

Chapter 1: The American Dream Gone Awry

Chapter 2: Don’t Sell Yourself Short

Chapter 3: How Entrepreneurially Ready Are You?

Part II: Size Matters!

Chapter 4: Company of One

Chapter 5: Boss of a Few

Chapter 6: Business of Many

Part III: To Build or Buy? That Is the Question

Chapter 7: Buying a Franchise

Chapter 8: Buying an Existing Business

Chapter 9: Building Your Own Business

Chapter 10: To Partner or Not?

Part IV: Start Your Engines!

iv Be Your Best Boss

Chapter 11: The Road Map: Business Planning

Chapter 12: Fuel Up: Finding the Funds

Chapter 13: Gaining Traction: The First Six Months

Chapter 14: Acceleration: Six Months to Two Years

Chapter 15: Full Speed: Two-Plus Years

Part V: Where to Next, Boss?

Chapter 16: When and How to Exit

Chapter 17: The New American Dream

Epilogue: Entrepreneurship on Steroids

Additional Resources

Notes for My Business Plan

Relevant Reading and Research Material

Take This Myth-Busting Quiz

The Full Picture of 401(k) Funding


About the Author


Large, impersonal institutions confer degrees without wisdom; infomercials and seminars offer “coaching” that all too often is little more than a DVD set and more sales pitches

Bill Seagraves and his wife, Theresa, are a refreshing exception to that sad norm.

The irony is, Bill’s business of enabling entrepreneurs to self-fund their businesses in no way requires that they be. Bill could just as well operate like an attorney: rubber-stamping transactions, dotting i’s, crossing t’s, and forwarding paperwork.

Instead, Bill brings a huge added value to his financing expertise: he doesn’t let his clients buy businesses they don’t belong in, and he ensures that they embark on the entrepreneurial journey with eyes, ears, and sixth sense wide open.

Having coached thousands of entrepreneurs myself as a Google AdWords consultant, I can assure you this kind of mentoring is sorely needed. Bill won’t let you become his client unless you’re truly qualified. He stands at odds with thousands of biz-op salesmen whose only criteria for taking your money is that you have some to take

That is why I’m recommending this book to you. It will take you on a journey, not only of business discovery, but also of self-discovery. Bill will explain not only the mechanics of funding your own enterprise but also how to adopt the mind-set and mental toughness that business in the twenty-first century requires.

One last word: Just like the jungle is not for domesticated pets, the entrepreneurial path is not for everyone. Many would-be entrepreneurs are merely armchair quarterbacks, living their dreams vicariously through others. They read self-help books and dream of manifesting their personal greatness but never actually do it. Others start their journey with gusto and come back in body bags.

Bill Seagraves is worthy of being your advisor. Read this book and find out if the entrepreneur’s journey is

iv Be Your Best Boss

truly for you.

Perry Marshall

Chicago, Illinois

Perry Marshall is the best-selling author of Ultimate Guide to Google AdWords, Ultimate Guide to Facebook Advertising, and 80/20 Sales and Marketing


I always want to drive. Everyone else is welcome to be my passenger.

Even if it’s just for a jaunt across town with a client or business colleague, I’m the one who whips out my car keys before anyone else can. It’s always been that way. Ever since I got my driver’s license, I’ve found a way to be the driver whenever I can. Group going to a party? I happily designate myself the sober chauffer. Family trip and my wife offers to drive? I insist that she relax and enjoy the sights.

Even considering the hundreds of microdecisions and the risk and responsibility inherent in driving, I prefer it over being a passive passenger. Until I began writing this book, I didn’t realize how much this preference carries over to my business personality.

When I used to work for other people, I was at the whim of their decisions. Even if I saw a potentially better road to take, I couldn’t go there unless my boss condoned it. My employer’s hands were on the wheel, not mine.

I liked corporate life in many ways, but I could not stand this lack of control. So in 1995 I stopped being someone’s employee and became an entrepreneur, which I remain to this day

My need to be in the driver’s seat extends to money. I could not tolerate the fact that the hard-earned funds in my 401(k) were at the mercy of a volatile market. Late in 2003, during the downturn that followed the dotcom bust and the events of September 11, my wife and I began investigating nontraditional ways to invest our retirement funds. (Wall Street options were not cutting it, to say the least!)

Through readings and discussions with advisors, we learned that it was possible to invest retirement funds in your own business—without having to get in debt, without tax penalties—using a self-directed 401(k), or “rollover as business start-up,” as the government calls it. I only wish I had known that eight years earlier, when I bought my first business with a seller loan!

Bill Seagraves is worthy of being your advisor. Read this book and find out if the entrepreneur’s journey is

iv Be Your Best Boss

One evening at dinner, my wife and I noted how few people in our respective business circles, our community, and among our friends and family had even heard of the self-directed 401(k). We felt lucky to have stumbled across the information, but it got us thinking, What if we made it our business to teach other entrepreneurs about this funding option?

So that’s what we did. Eventually, CatchFire Funding was born. Since then, we’ve helped thousands of Americans who have been downsized out of a job, are afraid of being let go, or pine for the freedom of entrepreneurship for a variety of other reasons

I know what it feels like to want that freedom and at the same time to be afraid of the unknowns involved in the leap from employee to entrepreneur

My record hasn’t been flawless. I sold one business because it ended up being the wrong long-term fit for my skills and interests. In another instance, I broke up (badly) with a business partner. And a third company stayed too long in my living room with a growing staff.

But I learned from all my experiences, and I was good at getting the best business advice I could afford, at striking out boldly, and at following through—all the ingredients for long-term, profitable entrepreneurship

In the pages of this book, you’ll meet dozens of new entrepreneurs from across America—former corporate warriors, public servants, or other employees who have now bought or built businesses of their own.

Their ventures range from one-person companies to businesses with a larger staff. They make products for, or supply services to, all kinds of needs in the marketplace. These once reluctant entrepreneurs range in age from their late thirties to early sixties, and they all made the leap from employee to entrepreneur midway through their careers.

You can glean lots of practical advice from these entrepreneurs’ stories (and from me, as their business coach), including pros and cons, tips and tricks, and red flags. This book also offers useful checklists and worksheets. There’s even a quiz to help you assess your state of entrepreneurial readiness!

As you read this book, I want you to think: What’s my story? What makes me tick? What strength or passion am I overlooking or underestimating? Answer those questions, and you’ll be ready to reinvent yourself

iv Be Your Best Boss

and become the best boss you’ve ever had.

Let’s get your reinvention started!

To your success.

Bill Seagraves, president
CatchFire Funding
Parker, Colorado

Part I Are You Ready for a New Boss?

Whether you’re happily employed, recently unemployed, or hanging on to your job and sanity for dear life, you have something in common with every other person who will crack the cover of this book. You have a burning desire for something more, something better, something different and new.

This burning desire—whether an ember or a full-fledged bonfire—is all you need to keep your mind open throughout this first section. I promise there will be something everyone can relate to, and that you’re ready to hear it.


Chapter 1 The American Dream Gone Awry

I awoke racked with thirst, with a terrible crick in my neck and aching knees; economy class had never been kind to my six-foot-four frame. Flying high above the dark abyss of a nameless city, in who knows what time zone, I tried to picture what my wife and kids were doing while I was on the road . . . again. Soon I’d be catching up on family stories, but I wouldn’t be home long enough to join in on new adventures

But, hey, I had a source of steady income, to keep my family fed and housed and to finance some of our kids’ dreams; a boss who (sort of) liked me, and I was making half-decent use of my skills and education. I was living the American dream, or at least the dream my parents raised me to believe in—or was I?

As a company man, I found myself increasingly talking myself off the ledge. My mental checklist went something like this:

Comfortable? Check.

Respected? Most of the time.

In control? Nope.

Confident about retirement? Not really.

Satisfied? Meh.

Happy . . . ?

In the grand scheme of life, weren’t those last couple of things the most important? And in control? Ha! I felt trapped by the lifestyle I’d created for myself and my family, knowing that—at the whim of my boss or under the guise of downsizing—it could all be gone in an instant. The high-priced Silicon Valley home, private

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day care, a master’s degree for my wife, family vacations . . .

I was certainly not holding my own hand of cards in life! Even if I stayed in the company’s good graces, the best-case scenario was that in eight to ten years I could have my boss’s job (which I really didn’t want), and then what?

What if—I thought with real horror—I became unrecognizably removed from what I’d once set out to be?

Before I could stop it, I was flooded by memories of my impassioned words to friends, back in my college days, about the ideas and goals that excited me. There were paths I’d never taken, that I still cared about . . .

To block out these thoughts, I stuck in my earphones and frantically flicked through the radio stations on the airplane’s arm rest, hoping the music would stuff down the rising lump of depression and anxiety inside me. There had to be a way out. No matter how good this career looked on the outside, I needed to find out how to make work good on the inside too

That Scary Twelve-Letter Word

As it tuned out, my route to personal happiness and financial success was to become an entrepreneur. To many people that twelve-letter word sounds lofty and alien. But even though its linguistic roots are French, “entrepreneur” does not translate to “fear of failure” in English. In fact, “entrepreneur” was originally a workaday word that simply meant “someone who undertakes a task,” or, to put it in American, someone who likes to “get ’er done.”

There are all kinds of entrepreneurs out there, but what they have in common is that they don’t want to work for a cold, uncaring organization but for someone who gives a damn. To that end, they realize that they themselves are the best boss they’ll ever have.

Be Your Best Boss 5

Getting the Boot

Maybe you’ve been given your marching papers after years of loyalty and hard work for a faceless corporation that’s decided it no longer needs or wants you. We all know lots of people whose lives have been turned upside down since the 2008 recession.

You might be one of them; you may be feeling, for the first time in your life, like you’re disposable. That’s not a nice feeling. All of a sudden you’ve gone from being a smart, successful, respected professional to (cue, inner voice) a nobody, worth nothing in today’s workforce.

Through the up-close-and-personal lens of your loss you may not be able to see the big picture behind your midlife career crash. And that picture is the baby boom’s megademographic wave. The workplace system of yesteryear that gave tenured workers (like your parents and their parents) steady raises and good benefits, eventually providing for a comfortable retirement, is no longer sustainable. There are just too many boomers for this model to continue working.

A lucky few employees made it out of the recent recession relatively unscathed. Then there are the rest of us. And even if you did survive the gory years, you may now be watching your employer shift focus to recruiting and retaining younger workers

Midcareer professionals, like yourself, are getting passed up for promotions and raises or forced into early retirement!

It’s Not Personal

This kind of ageism exists entirely because younger people cost less to employ. In the HR column of the ledger, you’ve become a liability—despite being an asset with regard to experience, skills, and maturity. It’s not personal—it’s business. Sure, it hurts to be overlooked, but the bottom line is that the bottom line is the only

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benchmark that matters in in the workplace.

Dan Murphy, fifty-nine, of Syracuse, New York, experienced this—on both ends. “As senior operations officer, every year I was challenged to do more with less, pushed to decrease the headcount. I pulled the trigger and did downsizing throughout my career.” Then the gun got turned around and pointed at him!

“My employers felt I had gotten to a certain age that I was old enough and too expensive,” says Dan. “It was easier to pay three twentysomethings half my salary and let them work their calves off.” He moved on, albeit reluctantly, and started his own business after almost two years of fruitlessly seeking a new corporate gig.

Don Rollins, sixty-two, also knows what it’s like to be overlooked as “too old.” When his employer merged with two other arms manufacturers—the result of government sequestering—Don learned he’d have to move to New York or the Midwest. He didn’t want to leave his native Florida, so he gave up his job as director of operations, and “Did what all corporate warriors do—started interviewing,” he says.

It didn’t go so well. “They saw my gray hair and read my résumé with my thirty years’ experience . . . then I’d go to the interview, and I could feel them thinking, How much runway does this guy have left?”

Don’s age turned out to be a blessing in disguise. He started his own business in Sarasota, Florida, a Signworld franchise—and he’s happy he did. “I sure as hell don’t miss the corporate world!” he says

What Are Your Options Really?

Maybe you’re not convinced that entrepreneurship is the answer. Maybe you’re obsessing about how to fit yourself back into the corporate puzzle. (Even if it’s an awkward fit, at least it’s what you know.)

But the fact is, the career landscape has changed. You’ve changed—certainly in the eyes of employers.

It is highly unlikely you’ll ever come across a job ad that reads like it fits you: “Seeking midlife employee with high salary demands and possibly outdated skill set. Likely to be disgruntled and in urgent need of replacement income due to family demands. Potentially overqualified and therefore likely to leave the minute

Be Your Best Boss 7

something better comes along.”

Julie Richter was the epitome of the disgruntled employee when she decided, at age fifty, that she could make something better come along—by herself. The Missoula, Montana, native was pretty jaded after many years as an employee in the insurance industry. “There are a lot of shenanigans and agents who only care about making the sale,” she explains. “I considered getting out of the business entirely.” Julie especially didn’t want to work for a company anymore, “versus working for the clients, which is more important.” She solved her crisis of conscience by starting her own insurance company, with her own clients to care for.

Not that it was easy. Julie admits, “I was afraid to leave a salaried, steady income and step into the unknown.” She has that in common with a lot of midcareer entrepreneurs, like Dan Murphy, who says, “It was scary. I had never been self-employed. I’d always worked for large corporations. . . . Never in a million years did I think I’d start my own business!”

While Julie chose to get off the corporate train, Dan was escorted off due to downsizing. He had been managing up to 250 people at a major financial services institution, and at first he wanted back into the corporate puzzle so badly, “I was even at the point that I was willing to relocate again,” he says. “But my age and income level scared new opportunities away—the same reasons for my downsizing in the first place!”

Are Your Golden Years Looking Tarnished?

What is going to change now, or in the future, that will give you enough of an income bump to make a real difference for your retirement dreams? A series of large raises or promotions? Stock options? A lottery win?

You’ve been working your butt off for “the Man” for years—and who gets a new yacht or a winter home in Florida? Not you. The top executives and shareholders at your company don’t need to wait until they retire to get those perks; they enjoy them now—courtesy of all your hard work.

How is your own retirement shaping up? Are you on track to get the golden years you’ve been dreaming of,

8 Be Your Best Boss

or is the gold looking a bit tarnished?

It’s possible in this day and age that you could end up being forced into early retirement by your employer. Is your nest egg big enough to cover your desired retirement?

Retired but Inspired

Even if you are already comfortably retired, you may be driving yourself and your spouse crazy with too much time on your hands. (After all, there are only so many things you can fix around the house!) Maybe you miss giving back to your community. Or it’s possible that retirement is costing more than you anticipated, and you aren’t sure how many more years of quality retirement you can afford.

In any of these cases, entrepreneurship could be an attractive option. You’re not ready to be put out to pasture—physically and/or financially. You may be retired, but you’re still inspired (to make a buck).

Keeping Your Roots

It’s a common scenario in this day and age of mergers and acquisitions for employees to be asked to uproot their families and relocate out of state, or even out of the United States, to accommodate a company’s change in ownership. But you might be reluctant to move your spouse from a good job and your kids away from school and friends. Or maybe you don’t want to be too far away from your aging parents. In any case, relocation by your employer may not be a viable solution for you.

Mike Pred, a global vice president at a leading health-care corporation, was given an ultimatum: he could relocate out of state or lose his job. He and his wife decided not to pick up and move their daughter during her high school years. Mike looked around at other work options and “Concluded that I could eventually replace my

Be Your Best Boss 9

income with a PrideStaff franchise while building an asset that could achieve a rate of return that would exceed what I could get in passive investments like the stock market.” He made the decision to leave the corporate world in November 2013. “I have not looked back,” he says.

Don Rollins faced the same kind of “relocate or you’re out” choice from his corporate employer. In his case, the kids were all grown and on their own, but still Don and his wife didn’t want to leave their native Florida. What Don does now, building signs for his franchise, is certainly different from being an engineer at an arms manufacturer, but, in his words, “I still get to build stuff,” and he doesn’t have to give up his daily contact with other people—something Don admits he just could not envision for himself, despite being, at sixty-two, close to the (old school) retirement age. Visiting customers, working alongside his employee, chatting with other local business people in the region where he lives and works—that is Don’s lifeline.

If Not Now, When?

Even if you’re still employed, you may see that you’re running out of road. Your company is letting your colleagues go, one painful batch at a time, and you suspect that your number is coming up. Like a deli ticket from hell, the waiting game is as bad as, if not worse than, actually receiving the pink slip!

Maybe you’re stuck in a job you longer enjoy and you’re pining for a change. You’re the one who tells family and friends at each Christmas party, “This is the year I’m going to make the jump and be my own boss.” And then nothing changes. Sure, change can be scary. But feeling stuck is worse

Or maybe you’re not looking forward to a passive retirement; many baby boomers aren’t as comfortable with that as previous generations were. Dave Young, forty-nine, of Jackson, Missouri, says bluntly, “I’m not a big fan of saving your retirement funds to use when you’re old, which aren’t your best years.” Dave is using that retirement money now, injecting it into his dream business (a start-up kennel and breeder).

About his own reinvention from employee to entrepreneur, Tom Macari says, “Sometimes it’s just ‘put up

10 Be Your Best Boss

or shut up’ time!” In 2012, Tom applied for a job as police chief in Cripple Creek, Colorado, a historic gold rush town on the southwest slopes of Pikes Peak in the Rockies. He and his wife, Pattie, stayed at the area’s KOA campground, and, Tom recalls, “We half-joked that if the Cripple Creek KOA ever came up for sale we should look into buying it.” He didn’t get the police chief job, and they went home. Then, in June 2013, the Cripple Creek KOA came on the market. It was go time for the Macaris: they put their money where their mouths were and bought the KOA business.

Even if you’re younger—and nowhere near retirement—you may have had an epiphany like mine, where you realize you’re not chasing the dreams of your younger self, and you can’t see any good reason why not. Andrew Caplinger, thirty-five, went the corporate route for fifteen years, until he had a New Year’s Eve talk with his wife, Courtney, about where he was headed. They made a pact that by a year from that date he would have launched his dream business. He followed through—and Caplinger’s Fresh Catch Seafood Market was born in Indianapolis.

“I’ve known I’ve wanted to do this since I was a junior in high school,” says Andrew. “We were a bunch of business dorks in the marketing club. I was part of different competitions at the national level. At one, I had to write a business plan and present it to SBA loan officers. . . . My idea was a fish market and restaurant combined. I won at the state level.”

Andrew will tell you how good it feels to live up to the “boy wonder” he was twenty years before, and that all the work to become that entrepreneur has been worth it.

Life Changers

Then there are life-changing moments that remind us how short our time is on Earth—both for us and our loved ones. These experiences can really show us what’s important in life, and they may push us to embrace change now, rather than put it off anymore.

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Pete Dailey, forty-nine, had a life-changing experience involving his father that helped get him make the decision to leave his long corporate career as a meteorologist in 2014 and pursue his dream—a restaurant startup in Oakland, California.

“Dad and I sat and talked, just the two of us, in my apartment—it was the first time we’d ever talked about me changing my career,” says Pete. “Dad recommended that I do what makes me happy.” A couple of weeks later, his father died suddenly in his sleep. Pete was ready to make the leap to entrepreneurship.

Or it could be your own mortality that gives your entrepreneurial dreams a jump start. A serious health issue had Mark Olenick reviewing his priorities and looking more closely at his next chapter. “Getting a pacemaker at age forty-three will do that,” he says. Now fifty-one, Mark is going after his dream of starting a pickle company with his wife in Pennsylvania—instead of putting it off for “someday.”

Life changers can also include new relationships or a point in a long-term relationship where a couple reevaluates how much time they spend together

Michael Croteau can relate to the former situation. In his fifties, the aircraft mechanic wanted to find a job where he could work closely with his fiancée, Tina. So he left his career with a large aeronautical corporation and bought an existing business back east, where he grew up—a quaint vacation resort in the heart of the New Hampshire Lakes Region. “I wanted something that would support us and something that we could do together,” says Michael.

Velvet Shackles

If you are still working for someone else, take a moment to consider how the next decade will likely play out. Do you think you’ll have control over how and when your career ends? Will you even get a say in the matter? You could be wearing velvet shackles that look good and feel comfortable now—but shackles are still shackles

Michael Schaul, fifty-seven, knows about shackles, and how they can creep up on you despite your best

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intentions or how happily your career started.

Michael spent the first decade of his career with a large US oil company at its small offices in Africa, China, and other international spots. He loved the hands-on work he did there. “In my mind, I made more powerful decisions overseas,” he says

When Michael and his wife moved back to Chicago to start a family, he found the large corporate culture there didn’t offer “as much job satisfaction for me.” He missed being able to make fast decisions as a country manager who “ didn’t have to go up three layers of management for approval.” So despite better pay and great exposure, he left corporate America and started consulting for a couple of years (“loved the work, hated the travel”), then bought an apparel company in Wisconsin. So began Michael’s satisfying twenty-year entrepreneurial journey.

Layers of management and the “analysis paralysis” of the boardroom-meeting culture are shackles that former corporate warrior Mike Pred does not miss. He says he and his employees at his PrideStaff franchise in Lilburn, Georgia, “can focus our efforts on what we determine to be the most valuable—and eliminate the cumbersome elements of decision making in the corporate world.” Mike adds that as an entrepreneur, “There are no excuses, no finger pointing, and no politics. . . . I know that the results of my business totally hinge on my effort and the team I put in place.”

Amy Shellart is clear about why she launched her own business, the Goodness Locker Inc., in Springfield, Missouri. “I need to be in charge of my own destiny. . . . If I piss off my boss, I can’t provide for my family,” says the forty-one-year-old who is raising two preteen kids with her life and business partner, Christina Hesse.

Whether you’re motivated by inspiration or desperation, whether you are pursuing a dream or adapting to the changing workplace—shaking off the shackles is worth the effort. And here’s some more good news: you’re likely in a much better position to become an entrepreneur than you think!

The Legions of “Yeah, Buts”

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Sometimes entrepreneurs start out with a bunch of “yeah, buts” that explain why they can’t, or shouldn’t, start their own business. These may sound familiar.

“Yeah, but I don’t have time to start over with a new career, not at my age!”

Here’s the thing, though: you’re not starting over! It’s not at all like coming out of college. You’re bringing with you a whack of real-world experience, maturity, people skills, money management skills, and more. A move to entrepreneurship at a later stage in life is more like a transition, a reinvention, than a start-up.

Dan Murphy knows this because in the business he bought, he handles all the sales and marketing (he’s a common sight, in his region, driving his branded SUV), as well as bookkeeping. His college education in finance plus three decades working in the banking industry have been a huge asset, as has all that time working with other people. (Let’s see a twentysomething bring all that to the party!)

“Yeah, but I don’t know anything about entrepreneurship—I don’t even know what I don’t know!”

It’s true, you may lack exact knowledge of what knowledge you’re lacking, but relax—you can get up to speed pretty quickly. Because you’re mature, have made years’ worth of big decisions, and have good people skills, you won’t have any problem

  • researching all the options out there,
  • seeking out conversations with entrepreneurs who have ventures similar to what you’re considering,
  • surrounding yourself with experienced professional (such as financial and legal) advisors,
  • and weeding out misinformation by running it past those trusted advisors.
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“Yeah, but I don’t have the money to finance my own business. I have bills to pay and kids to put through college!”

Finding the funding for your new business is a serious hurdle, but there are more ways around it than you think. Debt is not your only option! There are options such as self-directed retirement funds (without tax or penalty). Many people are holding on to their retirement funds, whether in a 401(k) or IRA, because, frankly, they just don’t know that those funds can be rolled over into a new business.

“Yeah, but don’t half of all new businesses fail?”

Starting a business is hard work but, then again, so are most worthwhile things in life. How easy is raising kids? How easy is it to stay happily married long term? You know the odds of matrimony failing, but that doesn’t stop you from giving it a try!

Besides, failure is not really an option if you do your research and due diligence, invest wisely, and give your new business 100 percent of your effort.

If you focus on other people’s failures, how can you emulate other people’s successes? Stick with the winners. Avoid the losers.

David Coleman knows about fear of failure. The corporate man turned owner of USA Auto Glass of Naples, Florida, says it can be frightening to start a business, “Because now you’re responsible for your own self and, in many cases, employees too. But, by the same token, if you’re one of those employees, you’re going to be stuck in that hamster wheel for the rest of your life.”

He adds, “The initial work [as a business owner] transforms itself further down the road into a lifestyle that most people can’t imagine. It just makes it so much easier once you attain that level—it becomes enjoyable again to go to work!

Don Rollins, the sixtysomething Signworld franchise owner, says that “Being an entrepreneur is not a lazy

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man’s deal. . . . It’s a whole lot different than back when I had a staff to delegate work to.” But he adds that now all his hard work directly benefits him, and not some employer: “It’s my money. It’s my deal. I can make decisions as I see fit.”

“Yeah, but everyone says I don’t have what it takes to be an entrepreneur!”

We’ve all, at some time in life, found ourselves at the end of other people’s “head trash”—the sort of knee-jerk negative reactions family, friends, coworkers, even strangers, can have to an idea they aren’t familiar with. Sadly, this head trash will likely appear when you start talking about entrepreneurship and how you’re going to do it.

Joseph Davern, owner of Davern’s Tavern & Lounge in Justice, Illinois, knows the feeling. Soon after he learned about the self-directed 401(k) funding option, Joseph says, he dealt with serious skepticism from family members, namely his brother, who was a vice president of a large company. “He was convinced that the transaction was impossible,” recalls Joseph. After a few more talks with CatchFire Funding, Joseph’s brother “actually got on board.” Joseph didn’t let a beloved sibling’s doubt deter him from pursuing entrepreneurship.

When Mark and Tracey Olenick, of Venango, Pennsylvania, started their pickle business from scratch while raising four young children, Mark left behind a twenty-year corporate career. “Everyone had lots of opinions on what we should do,” Mark recalls. For example, Tracey’s father said, “I would never do it, but if anyone can, it’s you two.’” That’s a nice touch from Dad, throwing in his vote of confidence while sharing his own fear of entrepreneurship.

Naysayers will always exist in the world, and most of them don’t mind weighing in! But here’s a critical tip: do not seek validation from people with no entrepreneurial experience. Their concerns could be wellmeaning, but they aren’t backed up with credibility. It is not your job to convince everyone else that you’re making a good decision. (Convincing your spouse and your bank is another story!)

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“Yeah, but I don’t want to lose the friends I’ve made at work.”

Maybe you’re worried about your professional social life. If you have a network of colleagues and friends you spend time with at the office, and sometimes even during off-hours, will life as an entrepreneur be lonely?

It might be—at least at first. The corporate world and the entrepreneur / business-owner community rarely overlap. Moving from one to the other can be a difficult adjustment, but it’s up to you to build a new network of friends and colleagues you can trust. (Of course, your family and nonwork friends aren’t going anywhere, regardless of the type of employment you choose.)

As Peter Dailey, who became a new entrepreneur in Oakland, California, after decades as a career meteorologist, says, “I may miss the people, the friends I made at work, but I sure don’t miss the cutthroat corporate world!”

“Yeah but what I really love to do won’t make a viable business.”

You’d be surprised. You may have heard the expression, “You tend to be good at what you love doing.” Well, it generally holds true that if you start a business based in something you’re passionate about—and you have the skills and there’s a market demand, of course—you’ll be successful. It just makes sense. We get good at what we do over and over, by choice, and often that begins as a hobby or side occupation. Adore going to dog shows? Have you looked into how many breeders or kennels there are in your area? Always been a computer nerd? Look into running a computer-repair service. You get the idea. So go for it!

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