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While taking some time off after selling his Chicago‐based company, MusicNow, to Circuit City in 2004, founding chairman and CEO Chris Gladwin had a new idea. It came to him while musing about how to store his extensive collection of photos on his personal computer. There just wasn't enough storage on his computer to house all those pictures.

Storing those keepsakes online in the cloud might work, but Gladwin worried they might then, outside of his control, be subject to loss or perhaps hacking. Not surprising, since he's an MIT graduate, Gladwin began reading books on encryption, and a really big new idea came to him that could alter the way data (including his and others' pictures) were stored and secured.

He realized that the execution of his idea would require forming a high‐tech company, putting together a team that could pull it off, and raising a lot of capital. While his MusicNow was a nice little company, a truly high‐technology startup with this big of an idea had not been developed and funded in Chicago in many years. Such startups had been gravitating to places like Silicon Valley, the towns around Boston's Route 128, and the Washington DC metro area, so the decision to try to do all this in Chicago seemed on the surface to be potentially as risky a decision as going after the big idea in the first place.

Chicago, like many other cities, had once been a hub of bustling entrepreneurship, with many hard‐driving, creative, fearless minds conjuring up the future. But such innovators—like Marshall Field in retailing, Potter Palmer in retailing and real estate, Michael Burke in telecommunications (Tellabs), the Galvin Family in electronics (Motorola), and Casey Cowell in data communications (U.S. Robotics)—seemed to be “yesterday's newspaper.” Until Chris Gladwin came along, there had been a long dry spell, and never in the dot‐com era had there been a high‐tech company created in Chicago that brought to the Midwest's commercial capital that virtuous cycle of local entrepreneur, assembling local talent, and capitalized through local funding.

The creation of that virtuous cycle depended upon not just Gladwin's big idea and his ability to assemble the required talent, but also his ability to attract the necessary funding—first from friends and family, then from local venture capitalists, and then from the wider world of risk capital.

Fortunately, Chris Gladwin had a lot of friends. Even better, some of them were individual accredited investors.

Once he exhausted that source of funds (which happens even to friendly people with big ideas), he turned to professional high‐tech venture capital investors. There were not many of these in Chicago, so it was a tough slog raising the additional $1 million he needed.

Fortunately for his new company, which he dubbed Cleversafe, Gladwin was (and still is) also a really decent, philanthropic sort. Practicing that philanthropic bent, Gladwin hosted a poker party with proceeds going to charity, to which he was able to attract several local entrepreneurs and venture capital investors.

One of the venture capital investors, Jim Dugan of OCA Ventures, knew Chris well and decided to back his idea, even though many other professional VC investors had already turned Gladwin down. Gladwin then went out on the road to find additional capital to join with Dugan and OCA, and ran into our then‐actively investing firm, Batterson Venture Capital. Our firm, along with OCA, recognized that with the rise of big data, big data storage and security were soon to be a big deal.

“Fairy Tales Can Come True, It Can Happen to You…”

The rest, as they say, is history. It may have taken a bit longer than we expected, and ultimately $100 million in investments over time, but when Cleversafe was sold to IBM in late 2015 for $1.3 billion, there were an awful lot of smiling faces in Chicago; 80 millionaires were minted among friends, family, and Cleversafe employees, and numerous already accredited investors suddenly became a lot wealthier.

Gladwin's big idea and its intersection with practical need resulted in market demand, and brilliant execution resulted in a home run win for the entrepreneurial Gladwin, the company's employees, and its venture capital investors. Many got back more than 10 times their investment. The very earliest investors made a multiple of 40 times their early investment. Cleversafe proved that a major high‐tech company could be created in Chicago in the 21st century, and so lots more are ready now to skip Silicon Valley and build their dream in the Midwestern heartland.

Opportunities like Cleversafe, while rare, are not unique. They are all around us, hoping for the risk funding—because venture capital is unquestionably risk capital—to enable them to turn their dreams into realities. This book will help you find them, understand them, and, with some pluck and luck, become a successful venture capital investor or VC‐funded entrepreneur. The result could be personal wealth, job creation, and a capital contribution to our country. Simply stated, we hope this book will help you win!

Leonard A. Batterson
Kenneth M. Freeman
Chicago, Illinois


Since the financial crisis of 2008–09, the American economy has struggled to grow at just 2%/year. Yes, there has been an extended stock bull market, but the bull must inevitably lose its vigor unless economic growth accelerates significantly.

With the stock market climbing sharply immediately following Donald Trump's election as our nation's 45th president, there are some betting that the Trump presidency will result in such an acceleration. We won't know whether such forecasts prove accurate, and to what degree, for some time. Stock market returns over the past seven or eight years admittedly look great, but that's due largely to the bounce‐back in prices following the devastating collapse of 2008–09. A look at the stock market over a more extended time frame presents a more sobering picture. Factoring in all the ups and downs, from January 1, 2000 to January 1, 2017, the S&P 500 index grew just 2.7%/year. Add dividends paid by the S&P 500, which have averaged around 2% annually, and you're looking at an average annual return of slightly below 5% over that period.

Moreover, the rise in stock prices to historical highs has been helped in recent years by the near‐zero interest rate environment, which has forced investors to turn disproportionately to stocks for any hope of decent returns. Therefore, even if economic growth accelerates, let's say to a 4% rate, the likely accompanying rise in interest rates to more normal levels should temper further prospective stock market gains.

Innovation: The Path to Wealth Creation and What Venture Capital Is All About

So how can the American Dream of wealth creation continue? The key is, and has always been, major innovation—new technology and new product development that address new needs or meet existing needs dramatically better.

The most successful major companies understand this. Today's Wall Street darlings—companies like Microsoft, Alphabet (the parent of Google), and Facebook—were yesterday's venture capital–funded startups. These companies understand that major innovation must never stop. Look at the publicized innovation efforts of Alphabet (now pursuing self‐driving cars), Tesla owner Elon Musk (racing to commercialize space travel), and the major pharmaceutical and biotech firms creating new cures for diseases that won't go away.

Automotive companies such as Volvo and BMW have established formal venture capital arms. Even marketers of mundane food, household cleaning, and personal care products, such as Unilever, are setting up venture capital arms to fund innovative startups in their fields whose growth prospects they can then nurture with dollars, distribution clout, and management know‐how.

So, a fair question from investors might be, why not just invest in the stocks of these big‐league innovators? We'd never suggest that you not invest in these companies. They've demonstrated the ability over the years to grow their businesses and stockholder value. There is one caveat, though. Their already high share prices have baked in investor expectations of continued healthy growth. Hence, you may earn a respectable return on those stocks, but don't count on breakaway gains.

The biggest wealth creation opportunity—for both entrepreneurs and the investors who back them—is through market‐changing innovation commercialized by new ventures. There are the latest winners, highly valued new ventures you've heard about—Uber, Airbnb, Instagram, Square, and many others. There are also the home runs that aren't household words. We just told you about one in the Preface that enriched many of our Batterson Venture Capital investors, a company called Cleversafe. Cleversafe's revolutionary innovations in data storage turned roughly $100 million in investments (to be clear, only about 4% from Batterson Venture Capital) into a $1.3 billion sale to IBM. And there are some doubles and triples out there, too, though the biggest money is to be made on the home runs.

As awareness of recent venture home runs has grown, there has been a surge in innovative venture activity. It's no longer limited to Silicon Valley and Boston's Route 128. Venture capital activity is flourishing in New York, Los Angeles, the DC metro area, Austin, and anywhere where creativity, ambition, and the funds to nurture it are found.

Venture incubators and supportive angels are emerging everywhere. Cleversafe is a great example. While people often talk about the Midwest's conservatism and reliance on agriculture and heavy industry, Cleversafe's billion‐dollar+ win was created in Chicago. In fact, Inc. recently reported that Chicago (which is where our funds are based) is now second behind only New York City in the number of fast growing private companies on the Inc. 5000.

The dollar growth in venture capital investment reflects this broadened activity. Venture capital investments in 2015 totaled $59 billion, up 153% since 2005. Importantly for our readers, for the past couple of years, investments by individuals have caught up with the dollars invested by the big institutions. The rich potential returns from venture capital used to be restricted to an exclusive club of institutions and the mega‐wealthy, but are now becoming “democratized.”

Venture capital returns historically have been handsome, averaging about 12%/year. That's a lot better than the almost 5% average return from the S&P 500 over the past 16 years, and almost anything beats today's near‐zero interest rates.

Some venture capital leaders have done even better. The funds we've managed have generated investor returns averaging 28%/year over the past 30+ years. We've done that even through the dot‐com collapse of 2000 and the broad economic plunge of 2008–09.

Our secret approach in fact isn't really a secret. We've shared it openly in the past, and will share it with you in this book. It takes lots of hard work, screening hundreds and even thousands of venture opportunities to select the few that we believe could grow into billion‐dollar+ home runs. We review at least a hundred ventures for every one in which we invest. We usually get in early, while these ventures still carry low valuations, before others recognize their potential.

The exhaustive screening and due diligence pay great dividends. To be clear, we don't always get it right. But more than 35% of our investments have delivered some positive return to investors. While that might not sound so great, that's almost double the success rate of the industry in total. (It's like baseball, where a .350 batting average can win the batting title!) And our big winners like Cleversafe (and several others, including our multibillion‐dollar exits for AOL and CyberSource) mean lots of new wealth for our investors.

Before we go further, though, let's be clear. Venture capital investment is not for the faint‐hearted. It is a high‐risk—and potentially high‐reward—opportunity. Most new ventures fail. Just 10% of venture capital investments deliver the majority of all returns. In this book, we'll try to help you maximize your success odds and manage your risks. We don't believe that any investor should risk losing his or her proverbial shirt in venture capital.

It's a high‐risk, high‐reward potential situation for entrepreneurs, too. It's easier and lots less risky for talented, ambitious individuals to devote their talents to large, well‐capitalized enterprises and make a comfortable living. But for the most ambitious individuals (and often the most talented), many of whom don't want to live under the yoke of corporate direction and are determined to do their own great thing, that is not enough. They seek the gold ring that can be captured only by building their own market‐moving enterprise.

After they've started up by borrowing from credit cards and home equity lines and then tapping into supportive and hopefully well‐heeled family and friends, they need to find the even‐bigger funds to continue on. As startups succeed, their capital needs to realize their full potential grow sharply.

It's often said that venture successes inevitably take twice as long and require three times as many dollars as the entrepreneur expected. So he or she had better know what they're doing, and go after funds from the right sources—those who can provide the needed dollars today, as well as help in accessing the dollars they'll likely need later, along with the advice and professional help that may be even more critical to their ultimate success.

While this book was written to help both the investor and the entrepreneur learn what they need to know to succeed today, it should remain helpful for many years to come. Sure, like the economy and other markets in general, the venture capital playing field will change over time, just as it has always been changing and evolving. Nevertheless, the fundamentals will still apply.

Very simply, the venture capital marketplace exists to bring together: (1) investors willing to accept considerable risk in exchange for potential exceptional return on investment, and (2) entrepreneurs whose innovative developments are characterized by considerable uncertainty and risk as well as potential for outstanding wealth creation.

For anyone who thinks the greatest innovations are behind us and questions how much is still left to “invent,” we say thank you for leaving the wealth opportunity from future innovations in the hands of those of us who can still dream and think big. Humankind's ever‐increasing expectations and aspirations will inevitably motivate continued innovation. Add to that the needs resulting from natural resource constraints, climate change, and other environmental concerns, which we believe will drive even more innovation than we can imagine.

Here is a list of a dozen categories we believe will be huge opportunity areas for future innovation and new wealth creation, and we're betting there will be even more:

  1. Advanced materials
  2. Artificial intelligence
  3. Big data and predictive analytics
  4. Biological computers
  5. Biomedical
  6. The conquest of aging
  7. The genome
  8. Immunology
  9. The Internet of Things and of Everything
  10. Nanotechnology
  11. Robotics
  12. Virtual reality

Changes in the venture capital playing field will also contribute to making the coming years good ones for venture capital investors and great ones for entrepreneurs.

As we mentioned earlier, the accessibility of venture capital investment opportunities is becoming democratized. Today there are roughly a half million individual venture capital investors in the United States alone, and that number should expand dramatically in the coming years.

Recently launched online venture capital portals have opened investment access to America's estimated 10 million accredited investors (i.e., individuals and couples with net worth, excluding the value of their primary residence, of $1 million or more, as well as individuals with annual income of $200,000+ or couples with annual income of $300,000+). Further, the JOBS (Jumpstart Our Business Startups) Act allows venture capital firms to advertise to these accredited investors.

On top of that, regulations implementing Title III of the JOBS Act, enacted by the SEC in the spring of 2016, open venture capital investment access, albeit with tight limitations, to the rest of America, too. These JOBS Act provisions should increase substantially the availability of venture capital investment dollars. What a great time to be an aspiring entrepreneur!

Entrepreneurs will be helped further by advances in software and Internet technology already behind us, which have brought down the costs of initial startup requirements. Lower‐cost startups are ideal for many online venture capital portals, even those restricted to accredited investors. These online portals typically set much lower minimum investment requirements than the more traditional firms, and so tend to invest fewer dollars in each of their deals. The new online portals open to non‐accredited investors, which are further limited by the SEC as to how much they can invest in a single deal, are also particularly well suited to startups with lower early capital needs.

Ironically, more traditional venture capital firms like ours, which only allow investments from accredited investors and, even though accessible online, set a higher minimum investment requirement (our new firm, VCapital, has a minimum individual investment requirement of $25,000), welcome these new firms that are democratizing the industry. Frankly, they are so new relative to the typical lead time from investment to return that it's too soon to say how well they will do for investors (more on that later).

Nevertheless, for us, the ability of a venture to attract a large number of these firms' smaller investors represents valuable market intelligence, demonstrating early concept appeal. It's somewhat like virtual market research. If the venture goes on to show progress and has greater subsequent funding needs for expansion, we may be more likely to invest. We may not get in quite as early, but the risk when we do get in (which will likely still be early in the venture's growth) will probably be less, too—an acceptable tradeoff.

Notwithstanding possibly lower initial startup funding needs, most ventures with considerable potential will have increasing funding needs as they progress. In some cases, particularly in fields dealing with information technology, the importance of speed to market may require quite sizeable later‐stage investments in order to accelerate expansion. In other fields, such as pharmaceuticals and biotechnology, later‐stage FDA testing requirements carry extremely large costs. The risks even at these later stages are still inappropriate for banks or most alternative lenders, requiring a venture capitalist's perspective and risk tolerance.

Putting all this together, it looks like we are actually just now entering the golden age of venture capital for individual investors and the entrepreneurs whose dreams they will be able to fund and then benefit from financially. This book is written for both groups—individual investors and entrepreneurs—to help guide them along the path to potential wealth.

Understanding the Major Players

The Venture Capitalist: Funder of Dreams

At the center of the venture capital playing field is the venture capitalist. The practical knowledge needed by both investors and aspiring entrepreneurs begins with a general understanding of this strange and extremely small population of individuals.

This chapter will get into a general description of our unique breed. Chapters 4 and 8 will then get into the distinguishing characteristics that investors and entrepreneurs, respectively, should consider in deciding which ones to invest with or to seek out for funding.

There are many ways to think about the venture capitalist. One is to liken him or her to a marriage broker. At its most basic level, the venture capitalist's reason for being is to bring together investors' dollars with entrepreneurs who need their money. Of course, the investor has to want to invest in that entrepreneur's venture, and the entrepreneur has to be willing to accept the investor's terms. The venture capitalist as marriage broker needs to sell both sides.

The venture capitalist is also like a marriage counselor. The “VC” helps the two sides—investors and entrepreneur—communicate with one another, often counseling the entrepreneur to enhance his or her venture's success odds. After all, the venture's continued progress and potential for ultimate success along with its attendant rewards are what will keep the relationship between investor and entrepreneur together.

Of course, one could describe the venture capitalist in other ways, too. The venture capitalist is part riverboat gambler, part security analyst, part trader, and part entrepreneurial voyeur.

Venture capital is a high‐risk/high‐potential‐reward endeavor, so not surprisingly, venture capitalists are calculating gamblers, instinctively balancing the risks and rewards. No venture capitalist can win every time, but the successful ones' winners will handily compensate for the losers.

Successful venture capitalists have intuitive and analytical skills. They must be able to assemble and digest large amounts of data—some precise but some pretty vague and incomplete—and integrate all that information in order to make seriously consequential decisions.

The venture capitalist must be an astute trader and negotiator, the kind of talent Donald Trump would admire. To succeed, he must figure out what he can sell to whom (like deal potential, deal terms, and ultimately the successful venture he has funded and nurtured) and what he can buy from whom (professional services, shares of high‐potential ventures) at a favorable price.

Even the successful venture capitalists, though, will lose more often than they win, so they must have confidence and strong egos. While recognizing that reality—that they'll lose more often than they win—they still must be able to state unequivocally that they believe in this entrepreneur and his or her venture, and to back that stated conviction with theirs and others' money.

The venture capitalist must often be a skeptic, as he is likely to reject a hundred deal opportunities for every one in which he invests funds. He also must temper the optimistic fervor of the entrepreneur. That's important at the start in order to negotiate a good deal and then later to foster the entrepreneur's management discipline and ensure the entrepreneur recognizes key risks and addresses them thoughtfully. At other times, he must be a business romantic, recognizing and accepting his limited control over the entrepreneur's operations and therefore often having to suspend lingering disbelief.

Venture capitalists must be extraordinary at living with and managing through ambiguity.

  • Ambiguity in that not much can happen before he or she has investor money in hand, and often that money must be secured before he can even tell the investors the deals he has to offer.
  • Ambiguity in that he or she must read between the lines, as investment decisions must be made before much of the information one would like is available.
  • Ambiguity in that the investments are usually highly illiquid; most must be held for 5–10 years, through good times and bad, before success or failure can be known.
  • Ambiguity in that entrepreneurs may love him as their essential source of money and yet hate him because of the controls and limitations he may insist on imposing in exchange for that money.
  • Ambiguity in that investors must think enough of him to invest with him, may then grow impatient and displeased, waiting so many years for a return, and then love him dearly for the stellar returns he may ultimately deliver.

Venture capitalists must also have the confidence to live with frequent adversity. Almost all ventures in which he or she invests don't go quite as planned at the start. Most go through the valley of death at least once. Buckminster Fuller once wrote, “Sometimes I only find out where I should be going by going somewhere I don't want to be.”

Most of all, the venture capitalist needs to be a business generalist. He or she is often required to provide not only know‐how but also “know‐who,” to know the resources that the entrepreneur needs to best solve specific problems. Often the venture capitalist needs to know a lot about the particular industry, market, or technology in which he is investing his investors' funds.

Importantly, the venture capitalist must be highly knowledgeable about business development. That means sometimes being a patient nurturer of growth, but at other times being the impatient, sharp prod pushing the entrepreneur. Most people involved in business creation create just one business in a lifetime; the venture capitalist is involved in building many.

The venture capitalist must be an astute strategist. The ventures in which he invests are inevitably on the cutting edge of markets and technologies, so often those ventures need to make sharp strategic turns as more is learned. The successful venture capitalist must be able to participate in driving the venture's strategic path. Both investors and entrepreneurs need such VC skill.

Perhaps surprisingly, the successful venture capitalist must sometimes display exceptional operating acumen as well. While in most cases the venture capitalist will not get heavily involved in portfolio companies' day‐to‐day operations, there are times when the VC must step in, right an errant venture ship, and spearhead the turnaround of a venture that still has valuable potential but has lost its way.

There aren't many individuals who have all these tendencies and skills, and even fewer who want to live life on the edge like this. There are only about 500 active venture capital firms in America. Given all the aspiring entrepreneurs and ambitious startups vying for the support of so few VCs, the entrepreneur needs to understand the time pressures they face and the schedules they juggle. Don't lose faith if the call you made or the documents you sent don't receive responses for several days. The message you get that the VC is out of town or in meetings and can't get back to you right away is likely the truth, so don't despair.