Startup Lifestyle

Mental Health Matters

In December 2018, Lyft’s co-founder and President John Zimmer broke new ground by speaking publicly about his struggle with depression. CNN’s Laurie Segall published an interview with Zimmer where he spoke about the challenges of competing against Uber, a company that raised 10 times the capital raised by Lyft. Though they provide similar services, press and analysts hailed Uber as the disruptor and treated Lyft almost as an also-ran. Critics wondered if Lyft would even survive. During this time, Zimmer found himself “in a dark place” and was “in a funk for several months”.

Sadly, Zimmer’s transparency is rare in the Silicon Valley. The pressures and burdens of a continuous, breakneck pace with minimal financial resources can leave entrepreneurs feeling like they are skydivers frantically trying to assemble their parachute while they are freefalling past 10,000 feet. The fact of the matter is that startup life isn’t all glamorous hack-a-thons and butter-smooth Agile sprints. Not everyone buys into your vision. Venture capitalists don’t regularly beat down your door to give you money. All apps don’t go viral. And considering the total number of startups, companies with billion-dollar valuations are almost as rare as the unicorns they are named after.

Routine Sprint-a-thons

The truth is that startup life is hard. Silicon Valley culture promotes an always-at-work lifestyle. When most of your colleagues work six or seven days a week, it creates a palpable pressure to follow suit. Small startups attempting to disrupt their market represent the ultimate underdog David vs. Goliath battle. The urgency to retain first-mover advantage drives an expectation of non-stop sprints. Most people understand that sprints and marathons are very different types of races, but Silicon Valley seems to sadistically believe that sprint-a-thons represent a sustainable way of life. For an emerging startup, it can feel like you’re in a perpetual state of crunch time.

In normal life, people who exhaust themselves sprinting to reach the finish line get some time to decompress and recharge afterwards. In startup world, the reward for meeting a deadline is usually the next crazy deadline. Instead of resting after working hard, recovery is replaced with playing hard, blowing off steam, and partying. Numerous news reports chronicle the under-the-radar substance abuse problem that is all too common among tech startups. This news stream seemed to peak briefly in November 2013 when former Google executive Timothy Hayes died from a heroin overdose aboard his yacht in Santa Cruz. It briefly spiked again in December 2018 when Colin Kroll, co-founder of Vine and HQ Trivia, died of an apparent drug overdose. Kroll’s father reported that his son routinely worked 100 hours a week. As co-founder of prolific payment provider Square, Tristan O’Tierney was set for life, but died in February 2019, likely due to an addiction problem he previously disclosed on Twitter.

Cognitive Steroids

In light of the crushing pace, employees need to be able to consistently perform at the highest possible level. In the tech world, it’s quite possible to have one developer produce 10 to 20 times more quality output than the next. Tech workers can be tempted to find a solution they believe will help them to continuously excel and produce, as the threat of failure can lead to the company replacing them with another hotshot new hire, or worse, in the company shutting down.

The challenge is that it’s nearly impossible to hit a home run every time you step to the plate. Major League Baseball was rocked in recent years by a series of reports that its biggest stars used steroids: Jose Canseco, Mark McGwire, Sammy Sosa, Barry Bonds, Rafael Palmeiro, Alex Rodriguez and many others tested positive for performance-enhancing drugs. All of these players had tremendous raw talent, but felt the need for just a little more juice to boost their abilities.

Since both athletes and tech workers are human, it’s inevitable that startup employees face the same temptations. Red Bull and coffee eventually fail to adequately feed the voracious appetite of the strive-for-performance engine, so it’s not a stretch to see people trying to upgrade to some form of rocket fuel. Where one industry enhances physical strength with steroids, another enhances knowledge worker abilities with psychostimulants.

Adderall, a prescription drug that treats Attention Deficit Disorder, is popular on college campuses as a cognitive enhancer. Its popularity as a “smart pill” has spilled over into the tech space as well. The lure of a smart pill is even dramatized in the movie and television series, Limitless. Adderall holds a reputation as a smart pill that helps high-functioning people become higher-functioning. This reputation exists in spite of a study by Dr. Martha Farah at the University of Pennsylvania that suggests “higher-performing people show no improvement or actually get worse” from taking Adderall.

It’s common for college students and tech workers alike to rationalize their off-label Adderall usage by thinking it’s just a stronger form of caffeine and not as addictive as cocaine. While there may be some truth about Adderall being less addictive than cocaine, dependence can still form due to the added release and absorption of dopamine. Like all drugs, Adderall also has a long list of side effects including hypertension and cardiovascular disease. In addition, all prescription drugs run the risk of triggering dangerous interactions with other medications. Finally, there’s still the fundamental issue of a workplace culture that leads people to illicit drug usage.

Superman Syndrome

Silicon Valley also worships the superhuman: hero hackers, serial entrepreneurs with multiple exits, and celebrity founders can all achieve rock-star status. But the reality is that most startups fail, including those founded by some of the world’s brightest and most promising people. Sometimes, the shock of failure for people who are used to succeeding becomes too much to handle. Or, even if the startup continues to operate, just the daily startup grind can become too much. Sadly, there are too many tales of promising, capable people deciding that ending their life is more appealing than continuing to fight:

  • Ilya Zhitomirskiy, founder of “Facebook killer” Diaspora, was rumored to have committed suicide in November 2011. He died 22 years young.
  • Eric Salvatierra, CFO of Skype, VP at PayPal, stepped in front of a train in March 2012. He was 39 years old.
  • Aaron Swartz, co-founder of Reddit, hanged himself in January 2013. He was just 26 years old.
  • Jody Sherman, co-founder and CEO of Ecomom, shot himself in January 2013.
  • Zaria Draganic, CEO of AltoCom, ended his life in March 2014.
  • Austen Heinz, CEO of Cambrian Genomics, committed suicide in May 2015. He died at age 31.

Silent Suffering

Many of these people suffered in silence because society still stigmatizes mental health needs. This is sad because mental health challenges are more common than we may know. The National Institute of Mental Health reports that 19.1% (62 million) of American adults live with anxiety disorders and 7.1% (23 million) live with major depression. Research from Dr. Michael Freeman, a psychiatrist at UCSF, indicates that entrepreneurs are 50% more likely to have a mental health condition. So if 19.1% of the general population lives with an anxiety disorder, then about 29% of entrepreneurs suffer from anxiety.

People tend to react with compassion and empathy when someone tells them they have cancer. However, most people don’t know how to react when learning a colleague, friend, or family member has a mental health challenge. Responses vary from awkward silence to criticism (spoken and unspoken) of how the person must be weak in some way. If we are honest with ourselves, we are all weak in multiple ways. Anyone who has a hard time identifying their weaknesses probably struggles with pride or arrogance.

We can all help to de-stigmatize anxiety, depression, obsessiveness, or other conditions by treating people with mental health needs no differently than people with medical needs. Most people don’t bat an eye if a colleague or friend needs insulin to treat their diabetes or needs time off to recover from a broken bone. We should offer the same understanding and caring support for people who take anti-depressants or suffer from panic attacks.

Untreated Pain

I personally endured extended angst and anxiety for decades. I have always had very high expectations for myself and those around me. When I or those around me failed to meet these expectations, I usually found myself in a tailspin emotionally.

When I was CEO of startup #4, a number of circumstances led to serious problems on a big customer project. These problems resulted in missing several key deadlines, which ended up costing the customer a lot of money. The customer blamed us and threatened to sue. Since I had to personally guarantee the company’s finances, any losses would hit me hard. Resolving the customer’s problems and getting the project back on track stole my entire attention. In addition to the full-time job of running the company, I added about 40+ hours to every week working to avoid a lawsuit. I felt like I was playing an endless game of Whac-a-Mole, as clearing one hurdle only led us to the next obstacle. No matter how many hours we spent, we still couldn’t break through the logjam blocking the project. My stress level was off the charts for many months. I honestly started entertaining thoughts of ending my life. I welcomed the prospect of no longer having to deal with angry customers or threatening lawyers.

Thankfully, I had a strong support network. I reached out to many friends and mentors. Some really tried to help, but didn’t have the background to really understand the details of my predicament, so their advice didn’t address any of the root cause problems. (This actually added to my stress!) I had to persevere through this — knowing that people were trying to help — to get to those who had the background and wisdom to correctly identify and address the core problem.

One wise friend suggested I seek professional counseling. I initially bristled at the thought, as my prejudices reflexively took control. I didn’t want to appear weak. I didn’t want to have others potentially look down on me. I didn’t want to waste the time or the money. I doubted that a therapist could help me. In spite of all these excuses, the pain of staying the same was worse than the potential pain of seeking therapy. Engaging a trained counselor ended up being one of the best decisions I could have made.

After several sessions, I received a diagnosis of Obsessive-Compulsive Personality Disorder (OCPD). The name often creates confusion, given its similarity to Obsessive-Compulsive Disorder (OCD). Even though the names are similar, the conditions are vastly different. The Wikipedia definitions for OCPD and OCD follow below:

Obsessive-Compulsive Personality Disorder (OCPD)

A personality disorder characterized by a general pattern of concern with orderliness, perfectionism, excessive attention to details, mental and interpersonal control, and a need for control over one’s environment, at the expense of flexibility, openness to experience, and efficiency.

Obsessive-Compulsive Disorder (OCD)

A mental disorder where people feel the need to check things repeatedly, perform certain routines repeatedly (called “rituals”), or have certain thoughts repeatedly (called “obsessions”).

Basically, people with OCPD are perfectionists. In fact, a better name would be Perfectionistic Personality Disorder. In the workplace, OCPD can be viewed as a valuable trait, as perfectionists tend to do great work. However, OCPD can wreck your life or your relationships as you tend to repeatedly make poor, unbalanced decisions. OCPD made me see the distressed customer project as imperfect, so it was my job to fix it all, no matter what the cost personally.

If I or someone I depend on makes a mistake, I have a hard time letting it go and moving on. OCPD makes it hard for me to step away from work. I constantly think about work and will wake up in the middle of the night solving problems and refining business plans in my head. I struggle with healthy boundaries, always feeling that I need to make every deliverable great, even if the customer would be happy with good-enough. If left unchecked, I will spend excessive amounts of time and energy creating artwork worthy of a museum when a stick-figure drawing would have been sufficient.

As I worked with my therapist, we developed strategies to combat my obsessive tendencies. He helped me to build boundaries that vastly improved my quality of life. He even helped me to think differently about therapy. Since I love sports, I have no problem receiving coaching. As an advisor, I have no problem giving or receiving guidance and mentorship. I learned to think of my therapist as a life coach instead of a psychologist.

I’m grateful I listened to the advice of my friend. I have tools to help me live with my obsessive tendencies. My quality of life has greatly improved.

Similarly, when he was in a dark spot, John Zimmer received great support from his wife and from Lyft CEO, Logan Green. Zimmer advises us to invest into connecting with others, as that’s what matters most. In spite of the distractions that threaten to drown us, make time to meet with people in person. Care for others and allow others to care for you.

Into the Light

Thankfully, in addition to John Zimmer, several industry thought leaders are working to bring these real problems out of the shadows and into the light:

  • Ben Huh, CEO of The Cheezburger Network, wrote an amazingly candid post about his failures and why death once felt like a good option.
  • Brad Feld, an entrepreneur turned venture capitalist, and his wife Amy Batchelor, an activist and community builder, wrote a Startup Life, a book about “surviving and thriving in a relationship with an entrepreneur.” The book is remarkable in its transparency about their own real-life relationship problems.
  • Sean Percival, an entrepreneur and investor, wrote about his struggles with depression after a friend and kindred spirit took his own life.
  • Brené Brown, a research professor at the University of Houston, spent two decades studying courage, vulnerability, shame, and empathy. Her June 2010 Ted Talk on vulnerability included many personal and potentially embarrassing stories. It continues to be one of the most popular and impactful among their entire library of over 3,000 talks. Dealing with mental health starts with the willingness to be vulnerable and rebuff shame.

I’m grateful for each of the courageous souls who have chosen to be transparent with their challenges. Brené Brown’s transparency on stage in a large public forum literally took my breath away and made me sit up and pay close attention. She models the vulnerability her research advocates. Vulnerability is key to getting help and to building connections. Even though I’ve never met Brown, I feel a connection to her because her talks about vulnerability and shame resonate deeply with me.

Shame is a difficult problem, particularly in Asian cultures, where saving face and looking good seem to be top priority. The startup world faces similar challenges, as incredibly talented and successful people face obstacles larger than any they’ve previously encountered.

Trainers Needed (and Wanted)

Professional sports teams are built on the talents of the best athletes in the world. Every sports team includes a trainer to tend to the many injuries, both small and large, that athletes endure. Startups should learn from the sports world and provide resources to help founders navigate the turbulent world of entrepreneurship. Recent developments include:

  • Jake Chapman, a general partner at Alpha Bridge Ventures, published an excellent article on TechCrunch challenging investors and entrepreneurs to address the mental health crisis in startups.
  • Erin Frey, co-founder at Kip (, created an Investor Pledge for Mental Health on Medium. A growing list of pioneering investors have signed onto the pledge.
  • Mahendra Ramsinghani, Managing Director at Secure Octane, created an anonymous survey to collect mental health data from entrepreneurs. He plans to incorporate the survey data in a book he’s currently writing.
  • Mark Suster, another entrepreneur turned venture capitalist, issued a heart-felt plea to de-stigmatize depression and mental illness.

We can all amplify this small, but growing movement. Learn to recognize, acknowledge, de-stigmatize, and address mental health challenges. Accept others for who they are. Learn to fight against shame and practice being vulnerable — it’ll help you build connections with others that you’ll value. Invest heavily in your relationships. Entrepreneurs who’ve been to the brink and back consistent lobby for the need to keep your relationships strong.

Startup life carries a high risk of mental health challenges. Mental health needs to be viewed with the same importance as physical health. As you continue your journey down the startup path, investing in mental health will better equip you to achieve your goals while also minimizing your pain.


Startup Lifestyle

Beware of the Rat Race

In the early 1990s, a report circulated that listed Beirut, Belfast, and Hong Kong as the three most stressful cities in the world. Beirut, Lebanon, and Belfast, Northern Ireland were easily explained because, at the time, they were marred by urban battlefields, victims of political conflict and civil unrest. The third city, Hong Kong, surprised many as it was devoid of military conflict, governed by a reasonably stable political system, and considered a pillar city of Asian finance and trade. Many people built significant wealth, as evidenced by the fact that Hong Kong had the world’s largest number of Rolls Royce cars per capita.

However, in order to reach these levels of wealth, Hong Kong residents often work extremely long hours. A 2016 study from UBS Bank found that Hong Kong averaged the longest work week (50.11 hours), far exceeding second-place Mumbai (43.78 hours) by a comfortable 14.5%. This culture of self-sacrifice in pursuit of success brought a number of unwanted troubles. With stress comparable to that of a war zone, social problems were inevitable. Marriages suffered as many Hong Kong businessmen sought comfort by having a mistress in China. Common patterns of parent-child dysfunction were artfully captured in Amy Tan’s The Joy Luck Club. Kindness was so rare that the Chinese government ran television ads espousing the benefits of being courteous. The culture of stress even reached young adolescents, with many overstressed teens feeling the pressure to succeed academically. Tragically, many teens who failed to gain acceptance into a top college committed suicide.

Why Hong Kong Matters

Entrepreneurs may ask how what Hong Kong life has to do with startup life. Sadly, there are too many similarities. Both Hong Kong and Silicon Valley suffer from:

  • Out-of-control pursuit of achievement.
  • Over-emphasis on wealth as the key measure of success.
  • Work life imbalances, often manifested in regular 70+ hour work weeks.

Many people consider Kleiner Perkins to be one of the top two venture capital firms in the world. As the firm’s managing partner, John Doerr knows a thing or two about startups. In 1996, Doerr predicted that the Internet would lead to “the largest legal creation of wealth in the history of the planet.”

When Doerr made this statement, the market dynamics completely supported his claim. The Internet produced dozens of companies that, in just one to three years, created more than $25M of personal wealth for hundreds of founders. With such extraordinarily rich and rapid rewards, many people launched head-first into the startup rat race without a full understanding of the risks and potential repercussions.

The Wake-Up Call

About five years after singing the startup siren song, Doerr apologized and amended his earlier description of the Internet to “the largest creation (and evaporation) of wealth in the history of the planet.”

Doerr later realized the frenzy his statement helped fuel. Tens of thousands ran into financial, marriage, and family peril as they chased Internet fortunes. Founders often run into issues by:

  • Invest existing savings to fund their startup.
  • Underpay themselves to conserve cash — sometimes taking salaries near minimum wage.
  • Borrow from their home equity to fuel their startup.
  • Stop saving for retirement.
  • Accept inadequate, minimal cost healthcare coverage.

Sometimes the bets pay off, but more often than not they fail. The media and press enjoy telling the stories of the victorious. But since venture capitalists plan for a 5% success rate, that means for every one successful startup, there are 19 that fail or dramatically miss expectations. In my fourth startup (where I held the CEO role) I myself endured a six-month period where we skated on thin ice as three separate six-figure financial challenges all hit at the same time. As a founder, I had to personally guarantee the company’s liabilities. This meant I endured six months of off-the-chart stress wondering if I’d end up declaring bankruptcy and possibly lose my house.

Life’s basic necessities require cash. However, losing money pales in comparison to the relationship costs extracted by many startups. Because of the long hours, stress, and emotional demands, many entrepreneurs suffer broken marriages and/or physically or emotionally estranged kids. Having gone through five startups, I can personally attest to the fact that startup stress creates marriage stress. My wife and I have benefited from hundreds of hours of counseling to keep our marriage strong. This commitment required us to work through dozens of troubles — some caused by the startup, some just because life is hard. We’ve also counseled many married couples in their times of stress.

No company is worth sacrificing your marriage. No startup exit is worth realizing you missed your kids’ childhood years. Or worse, watching your kids walk down a self-destructive path while rejecting your efforts to provide guidance because you failed to build the connective tissue needed to survive their turbulent adolescent years.

Healthy Boundaries

Starting a company doesn’t automatically doom the founders to endless risks and personal troubles. However, founders do need to be aware of the pitfalls and install healthy boundaries. I suggest the following:

  • Put a cap on the number of hours you’ll work in a week or a month.
  • Make it your goal to be there for the little milestones along your child’s life. One of my mentors traveled 40+ weeks a year when he was running his startup, but made it his goal to always attend his sons’ high school athletic games.
  • Figure out ways to minimize your travel schedule by leveraging web meetings.
  • When you are in town, decide that you’ll have dinner with your family at least five nights a week. If you must, you can continue working after dinner, take a break when you put your kids to bed, then finish with no more than 1-2 more hours so you can go to bed with your spouse.
  • At dinner time, turn off the television so you can talk to each other. Have everyone share how their days went. Ask about high points or low points during the day.
  • When you are with your family, put your screens away, disconnect from e-mail and text messages, and be present.
  • Schedule a regular 3- to 4-hour date once or twice a month with your spouse or significant other (without the kids).
  • Schedule shorter 30-minute blocks of uninterrupted time to catch up with your spouse or life partner every two to three days. Protect these times as much as (or more than) your work meetings.

Basically, when you are limited in your time with your spouse or kids, make sure the time that you do have is quality time.

Stretched, Not Shattered

Be careful to avoid the hypnotic call to pour everything into your startup’s success. A quick Google search on “Hong Kong stress” reveals dozens of articles that inventory the social costs and impact of poor work/life balance. It’s fine to stretch yourself for a period of time to build and grow your startup. But it’s important to establish healthy boundaries to protect the things that matter much more than wealth or achievement. In this way, you can reach for success without shattering your life.

Startup Lifestyle

Take Care of Yourself

I’ve previously written about the importance of taking care of your team and taking care of others. It’s also important and acceptable to take care of yourself. I’ve already written about how startups tend to extract a pound of flesh and pint of blood. After running a marathon, you have to rest and recover. Take a nice vacation with your family. Treat yourself to something you enjoy.

After my last startup was acquired at the end of 2012, I finally allowed myself to buy a nice Nikon camera system. I gave myself permission to invest time to learn to be a good photographer. Four years later, I now shoot about 20,000 to 25,000 photos a year. Some photos are about creating fine art. Other photos are about capturing memories. Still other photos are about giving to others by making quality pictures of their special moments. Taking photos provides me with a way to wind down and step away from the frenetic pace I usually keep.

But in allowing yourself to explore your passions, it is important to do so within healthy boundaries. It’s fine to get a nice car, travel to see the world, or upgrade your house. But acquiring a fleet of super cars or buying a ten-bedroom mansion can lead to a life with unhealthy or non-existent boundaries. It can also provide fertile ground for your kids to grow spoiled, as effectively you are spoiling yourself. Instead, consider the examples of Mark Zuckerberg who generally drives a $30K Volkswagen GTI and Warren Buffett who lives in a nice, but still modest $650K house in Omaha, Nebraska. Both can clearly afford to indulge in multiple exotic cars and homes that induce envy even in the wealthiest celebrities, but they choose not to.

In order to keep me somewhat rooted, my wife encouraged me to blend my passion for photography with a way to give back. I decided to volunteer to teach photography to underprivileged kids and to raise money for our kid’s school. I also volunteer as an event photographer for several non-profits and schools.

So feel free to decompress. Enjoy life. Travel. Pursue a hobby. But as you do so, think about ways to build community or invest in quality time with your family as you pursue your interests. One particularly good way to stay connected and grounded is to volunteer in your kids’ schools. It’ll help you get a feel for a big part of your kids’ daily lives while also deepening your connection with them. In doing so, you will probably find that the relationships you foster and the community you build will provide more satisfaction than any prized possession or individual (isolated?) pursuit.

Startup Lifestyle

Take Care of Others

Startups provide great opportunities to grow. Startups are hard work, but they are fun, challenging and rewarding. And should your startup result in an exit, you can live comfortably, enjoying many of life’s good things. In the midst of your success, my encouragement to you is to share in some way with others. Besides just being the right thing to do, it keeps you connected with people and can ward off some unexpected maladies (like affluenza).

Financial security is a blessing, but it can also bring some hidden curses. We can easily fall into living an insulated life, leading to a privileged attitude. This becomes most apparent in your children. As parents, we want our children to have the best life has to offer. But as life enables you to have many things, children can develop an expectation of always getting their way. Kids can whine and insist on having the latest iPhone even though they just received a new phone last year. This happens when they haven’t learned the hard work needed in order to enjoy good things. You worked hard for your wealth, but your kids didn’t.

Warren Buffett’s Wisdom

While it’s not realistic to expect your younger children to earn a salary to pay for life’s expenses, it is reasonable to help them learn the value of hard work and stay connected with others who are less fortunate. One of my favorite stories is one where Warren Buffett was approached by one of his adult children for a $41,000 loan to remodel her kitchen. His response was epic: “You can go to the bank [to get a loan] like everyone else.” If you know anything of his life, you know that this response was not rooted in a selfish hoarding of his wealth, but in a desire to teach his family a set of values.

It Starts With You

Staying well-rooted starts with you. A parent who doesn’t set an example for their kids will wonder in frustration why their kids haven’t adopted their words of wisdom. Giving back to others is an important way to stay grounded. You don’t have to have the wealth of Bill Gates or Mark Zuckerberg to be able to share. If you’ve enjoyed an exit, you probably have more than enough to live comfortably.

Kishore is a friend of mine that sold his startup and subsequently started a charitable foundation to give back. His foundation drove an innovative, self-funding clean water project in India. In addition, Kishore heard of a young child that needed a costly surgical procedure that her parents could not afford, so he paid for it. Similarly, my own family is the beneficiary of someone else’s generosity. My youngest daughter is adopted from China. As an infant, she was left in the cardiac ward of a hospital because she needed open heart surgery to correct her VSD and ASD (two holes in her heart). She almost died several times, but a local businessman heard of her plight and donated the equivalent of seven years’ of a factory worker’s wages to pay for the surgical procedure. I do not know the man who paid for the surgery — I don’t even know his name — but my daughter is alive and thriving today because of his kind and generous gift.

Practical Paths

If you’ve decided to share, it’s important to plan. If you’ve received a windfall, make sure you consult a financial planner with many startup founders among their clientele. One benefit of being charitable is the opportunity to soften the tax burden in your years where your income will be abnormally high. Set up a charitable fund. Both Schwab and Fidelity have simple, low-maintenance charitable funds that you can participate in without being a billionaire. If you are fortunate to be in the multi-, mutli-million dollar territory, consult your financial planner about the benefits of setting up a charitable foundation.  (If you need a referral to a financial planner, I’ve had good relationship with Larry Steckler at Capital Financial.)

In addition to being generous with your money, remember to be generous with your time. Sometimes, it’s too easy to write a check and stay disconnected from true human need. Volunteer your time. When you volunteer, look for opportunities to talk to people you are helping. Listen to their stories. Connect with their difficulties. Involve your family — your kids might not be able to make substantive financial contributions to pay bills or fund a charitable cause, but they can still make a difference in someone else’s life by giving of their time and heart.

One of the things I’m most proud of is how my children give to support kids with special needs. My son just graduated from high school and has volunteered almost every week for over six years as a coach for e-soccer — a full-inclusion program for both typical kids and kids with special needs. He currently works a summer job helping children from low income families. He has developed an empathy and compassion for others far beyond the typical high schooler.

Startup life is amazing. There are great rewards professionally and personally. Should you be fortunate enough to enjoy an exit, remember to give back. When you give back, do so in a personal way that involves your family. You may just find that the rewards from doing so far exceed the benefits from your startup’s exit.

Startup Lifestyle

Take Care of Your Offensive Line

NFL quarterbacks are key to their teams’ success. And key to the quarterbacks’ success is the offensive line. The offensive line protects the quarterback in the passing game, while opening up running lanes to establish the ground game. The success of ground game activates the passing game by keeping the defense from just pinning their ears back and using the quarterback for target practice. A smart quarterback maintains a great relationship with his offensive line. Quarterbacks often treat their front line to fine dinners each week. Stories also abound of quarterbacks that present their blockers with expensive gifts such as Rolex watches, paid from their own pocketbook.

In the same way, a founder is key to the startup’s success. The founder manages the game, calls an audible at the line based on the defensive set, makes split second decisions, and delivers the ball where only the receiver can catch it. A seasoned founder also knows that his (or her) success is dependent on the surrounding team. Founders who take care of their people end up building strong, loyal teams. Should the startup enjoy an exit, the founders are in a position to ensure that everyone feels victorious.

During the negotiations with a potential investor or acquirer, founders should be careful to evaluate the impact of the terms of the transaction on the team in general. Even though these negotiations are fast-paced and stressful, founders need to make sure to run scenarios on how the transaction will impact the compensation of the employees. I’ve seen transactions go down where the executives preserve a reasonable equity position for themselves, but the rank and file employees get the short end of the stick. Put yourself in the shoes of your team. Would you, as a non-founder, be happy with the outcome of the transaction? Negotiate not just for yourself, but for your team. Where the numbers make it difficult and the broader employee base might get squeezed, can the founders carve out a portion of their own equity to make the employees whole?

In most exit scenarios, founders should have some room to share. Founders have much more equity than the average employee and can afford to be generous. There’s nothing wrong with founders earning a payout that is many times larger than the average employee. There’s nothing wrong with a quarterback getting paid many times more than a special teams player. The roles they play are dramatically different. Founders take the risk, flirt with failure, lead into uncharted territory, and shoulder the burden of making some of the most difficult decisions in the company. But in the same way that NFL quarterbacks take care of their offensive line, founders should remember the players that make success possible and be generous with their team. If you’ve done a good job as a founder, you’ll do just fine financially with the exit. Generosity results in the founders enjoying not just financial wealth, but also great friendships. Your team will appreciate the money, but will remember the loyalty. And as any older, wiser person will tell you, close relationships are more valuable than the size of your bank account, so do good and share.

Startup Lifestyle

Not Your Baby

Founders are a rare breed. They are driven by a vision of what can be to take risks. Founders often invest years of blood, sweat and tears to build and grow their startup. Given the amount of energy, effort, and sacrifice required, it’s not surprising that many founders consider their startup their baby. Some founders use this metaphor casually. Others use it quite literally. In light of the huge commitment required by a startup, founders have to be careful to maintain perspective and balance: a company is not a baby.

The Fun Toddler Years

It took a leap of faith for me to start my own company back in 2001. It was exciting to watch the small seedling that was my company germinate, take root and grow. The volume of work quickly exceeded our capacity and we began to hire employees and sign multi-year contracts. We nurtured and babied every customer. With a strong focus on providing technical expertise with phenomenal service, we soon grew to several hundred customers.

The Challenging Adolescent Years

And that’s when things got hard. Not every employee was the perfect hire. Not every customer was reasonable, nor did all of them pay their bills on time. As both the Chief Architect and CEO, I split my time designing highly available data centers while also securing financing and lines of credit to fuel the next stage of the company’s growth. We counted several top-15 e-commerce web properties and online marketing companies among our customers, including several with millions of daily transactions and billions in revenue. We grew faster than expected, meaning employees often bravely accepted responsibilities that they weren’t completely prepared for. Good employees rise to the occasion, but it certainly was turbulent at times.

As a first-time CEO, I include myself among the list of employees with more responsibility than ever before. I had to drive corporate strategy, negotiate legal terms, monitor cash flow, analyze markets, deal with angry customers, and ensure that we didn’t over-extend our resources. There were many pivotal moments where the company’s success or failure hung in the balance, and with it, the immediate livelihood of the employees and their families. During these times, stress and anxiety were off the charts. I found myself easily agitated and moody. I worked all the time. I wasn’t enjoying my family. My wife and friends wondered if I suffered from depression.

The Epiphany

Thankfully, I had a great support network. It was through this circle of friends that I got help. Several seasoned gray-hair types gave me perspective. I always considered my company my third child. This was my core mistake. A company is an asset, not a child!

A child is a person, with a beating heart, emotions, and the ability to feel both pain and love. A child is special and needs care, feeding, and connection. In return, a child gives wondrous joys and brings years of fulfillment. Every parent feels this – or at least felt it at one time.

A company is an asset – just like a car, a house, or a stock. Sometimes the asset serves you well and provides a fine return on investment. Other times, the car breaks down, the roof leaks, or the stock you bought loses value. When this happens, you either fix it or you replace it. Though many people spend hundreds of hours building up their car or perfecting their house, these assets don’t love you back. They serve you and we all need them, but they are inanimate objects and can be replaced.

I struggled with this concept at first, but I soon came to realize that life moves on even if your company doesn’t succeed. My wife and kids wouldn’t love me any less. Nor would their love be dependent on the size of our house or the material things in the house. Once I understood and accepted this concept, I was able to install healthier boundaries. I felt liberated. Don’t get me wrong: I still worked very hard to make the startup successful. I still shouldered the same weight, but I was now unencumbered. It was still a significant burden to bear, but I found much more peace and satisfaction with my daily life.

What to Do

We eventually sold our company, so in many ways it was a success. However, the business world is littered with stories of entrepreneurs who amassed small fortunes, but failed to find satisfaction or worse, lost their family in the process. A Google search on “deathbed regrets” is sobering. Click through the search link. Read several of the articles. Though death may seem far off for most, you shouldn’t wait until the end of your days to start living life to the full. Drawing healthier boundaries produces a harvest that you can enjoy now.

Every situation is different. Every founder has different skills, values and motivations. Every company has different strengths and weaknesses. But every employee in the company, from the largest stockholder to the entry-level new hire is a person. And every person needs to establish the right priorities to guide their life and their decisions. My advice to every aspiring startup founder is to seek a trusted group of seasoned and successful counselors to guide not just your company, but to guide you as a person first and an entrepreneur second.

Startup Execution, Startup Lifestyle

Startup Life

Startups are hard. Startups are rewarding. Startups suck the lifeblood out of you. Startups energize teams to overachieve. Startups expose your weaknesses. Startups develop your strengths. Startups periodically take a pound of flesh and a pint of blood. Startups provide deep gratification from doing your best and seeing something grow.

The right role at the right startup can be more educational than an MBA. Not all startups expect you to sacrifice your firstborn child to the gods of success. But not all startups are healthy environments. For individuals earlier in their career, finding the right fit to your skills and your goals is key. For those with some experience behind them (or those playing executive roles), building the right foundation and exercising good judgment is key to growing a healthy startup.

A Little About Me

I am a veteran of five different startups. I left the world of technical/management consulting in 1999 after my wife and I started a family. High-end consulting provides great opportunities to work with very talented people on very interesting customer projects, but the time and travel demands are difficult to balance with a quality family life.

I joined my first startup as an Engineering Director and was promoted to VP Engineering shortly before the company shut down in 2000, a casualty when the Internet bubble finally burst. I then served as VP Applications Engineering for another startup with fantastic market-leading technology, but various internal and external issues resulted in that company also shutting down. I then took a CTO role where I built a team that created the technology platform for a financial services compliance company. After successfully launching the application, I left the CTO role and founded my own startup. I learned a ton as a first-time CEO, culminating in a successful acquisition after seven years of steady, consistent growth. After working several years for the acquiring company, I felt the itch to return to my heritage and joined my fifth startup as VP TechOps. This fifth startup had a stellar engineering team that built the best product in the market, but was designed to run very lean, meaning everyone wore multiple hats in order to build and grow the company. Thankfully, Cisco recognized the value of the engineering team and the strength of the product and acquired the company.

Why I Write

I enjoy helping teams win. I enjoy coaching and sharing from my experiences. In some ways, writing this blog is a form of catharsis after many startup trials and tribulations. I’ve been fortunate to see several successes in my startup career. But the truth is, success wasn’t likely until I learned from several failures. The old adage that you learn more from failure than success is absolutely true.

Many seasoned experts and investors provide good advice on a variety of startup matters, but there are a few topics that I rarely see written about. I hope to cover several such topics over the next several months, from high-level strategy to low-level operational execution. I also plan to crossover and write about taking care of yourself so you can keep up with the ever-pressing demands of startup life. I believe in working to live, not living to work – a message that is sometimes lost in the Silicon Valley rat race. I plan to cover topics as diverse as startup job titles, hiring, product management, channel development, legal execution, giving back, and building a strong foundation for your life. I welcome your comments and hope you find something valuable for you and your situation.