A New Beginning: Lessons Learned

by Gregory VandenBosch

Hello and welcome.

Reflecting on writing the last post on my previous blog in which I attempted to distill years of startup learning into a ‘top-ten lessons learned’ list for entrepreneurs made me think that the same words may also be a good way to kickoff this blog.  My goal: think about the advice I’d want to give to the next generation entrepreneurs.  So, here it is:

1. Understand your motivation.  I believe it’s critical that you fully understand why you want to start a company.  Entrepreneur and author Steve Blank wrote that a startup, especially as a founder, is a calling.  And, if you’re not called to it, if you can’t get it out of your head, if you’re not passionately engaged waking up at 3 am making notes, if it’s not the first thing you’re thinking about in the shower and convincing your friends and family that this is the thing you need to dedicate your life to, don’t even think about doing it.

If things do work out and you’re fortunate enough to have your venture become successful, that’s terrific and it may be financially lucrative.  But, as VC investor Geoff Yang suggests, that’s really the effect not the cause.  The cause is that you’ve been completely committed to executing your vision.  Believe me, if it’s money or material things you’re after, if that’s where you tap real meaning in life  – then you will never have enough.  Never feel you have enough.  It’s the truth.  Remember, at some point very early on you’re going to have to convince other people to leave their jobs – to take salary cuts and gamble their careers on you.  Before you know it, you’re going to have dozens of people betting on you and the passion of your original vision, and it can’t be just to make money – that is not a sustainable driving passion.  Doing so would create a terrible culture and, long term, the company and/or your role in it, won’t survive.  It’s got to be about, as Steve Jobs said, making your dent in the universe.

2. Get started.  If you have conviction in life to be an entrepreneur, do it.  But, know for a fact, it’s not sexy and, in general, it’s pretty terrible.  It’s stressful, there are huge responsibilities, it’s lonely and it’s incredibly competitive.  But, if in your gut you think that it’s in you or you want it to be, this is obviously, as VC/entrepreneur Mark Suster submits, the single biggest gate in gating items that keeps most people from being entrepreneurs.

3. Beware of experts.  It’s difficult to do early on, but be wary of the “experts” that suggest they know more about your business than you do.  It seems like a perfectly rational approach to appoint authorities the task of evaluating your business.  However, I’ve found that “experts”, as a group, are perhaps the least suited to identify new ideas or assess your startup.  Most I’ve met are rote learners devoid of creativity.  They may possess a vast store of knowledge of facts, figures and detailed minutia of their particular field but they often lack the creative ability to venture outside the confines of their narrow field of knowledge and beliefs.  Don’t forgot, these people are guardians of the status quo who prefer to tinker with old ideas and models and dismiss new ideas with quick jabs that have a ring of authority but, in truth, often amount to nothing more than impressive sounding jargon outside of their expert fraternity knows the meaning of.

So whom should you turn to for advice?  It’s hard work, but there are experts who are not simply reciting old ideas in opposition to new.  There are creative thinkers who don’t subscribe to this approach – they don’t dismiss new and strange because it’s unfamiliar.  These thoughtful experts tend to not have quick opinions and rarely make quick negative pronouncements.  I’d start by looking for advice from people who’ve done it before – real life entrepreneurial experience, and from people who come recommended by people you know well and trust.

4. Don’t let your self-worth be completely defined by your company.  I admittedly struggled with this early on and, try as I may, continue at times today.   Over the long haul, I really tried to have fun with it.  I began to see my role as an entrepreneur as a game.  In some of my darkest moments I literally thought to myself, well, at least I’m going to figure out what bankruptcy is like.  So, if you can, as hard as it is, try to have some fun.  If you’re not having some fun or enjoying at least big parts of how you’re spending your days, why are you doing it?

5. Hire true believers. One of the things that I’ve come to believe is that as people are building their teams, entirely too much emphasis is placed on sort of the conventional notion of what appropriate qualifications are. “This person has a Master’s from this ivy-league school or that prestigious school.  Let’s hire him or her instead of the person who has a degree from this school which isn’t quite as good.” “Oh, this person has 10 years experience in your sector, as opposed to this person’s one year experience.”  I think that is a wildly overrated measurement for how to build a team. When you are starting out, I would encourage hiring people who would run through a brick wall, who are true believers in the mission of the organization’s product or service.  Even if somebody isn’t as smart or well qualified on paper as another applicant, in my own experience, it’s people who have the will and hunger to succeed that more likely than not are going to be the ones who end up becoming most successful.

6. Manage time like you manage money.  I submit that as much time and effort you put into figuring out how you are going to manage your capital, become similarly focused and ruthless about how you manage your time, because just as dollars drain out of your checking account, so to does time pass. And, in my opinion, time is the most precious resource for an entrepreneur.

7. Be careful from whom you take advice.  Australian screenwriter Mark Luhrman may have said best when he wrote that advice is a form of nostalgia and dispensing it is a way of fishing the past from the disposal, wiping it off, painting over the ugly parts and recycling it for more than it’s worth.   And yes, the irony of this isn’t lost on me.

8. Avoid bringing velvety leaders into your company.  It’s incredibly difficult, but don’t mistake charm and a big vocabulary with effectiveness.  Trust me, way too much of their time is spent avoiding bruising others, making themselves look like the “good guy” and positioning themselves for their next engagement or Board appointment – not leading.  I’ve found, in the end, they are ineffective and dangerous.

9. Protect your culture. First, it’s important to understand what culture is and what it’s not.  Culture is not company values or employee satisfaction.  It’s not, as Ben Horowitz explains, dogs at work and yoga – those are perks.  Rather, culture is a way to distinguish you from your competitors, a way to ensure that critical operating values persist such as delighting customers and helping your company identify employees that fit with your mission.  I’m deeply saddened that I didn’t do a better job protecting the culture in my company.  I’ll never make that mistake again.  So, where did I go wrong?  Turns out, surprise, it’s people.  In my case, just one person.  Harvard Business School Professor Howard Stevenson and author Eric Sinoway created a classification system to identify those employees that help an organization’s culture and those who hurt it.

  • Stars are the employees we all love — the ones who “do the right thing” (i.e. perform well) the “right way” (i.e. in a manner that supports and builds the desired organizational culture).
  • High potentials are those whose behavior we value — who do things the right way but whose skills need further maturation or enhancement. With training, time, and support, these people are your future stars.
  • Zombies fail on both counts. Their behavior doesn’t align with the cultural aspirations of the organization and their performance is mediocre. They are the proverbial dead wood. But their ability to inflict harm is mitigated by their lack of credibility. They don’t add much, but the cultural damage they do is limited.
  • Vampires are the real threat. These employees perform well but in a manner that is at cross-purposes with desired organizational culture. Because their functional performance is strong, they acquire power and influence. Over time, they can also acquire followers who share their different set of values.  Soon, there’s a small group of vampires and zombies that are slowly destroying the company from within.

When I mapped the company against these categories it was obvious we had a cultural vampire on the team.  In hindsight, the biggest mistake I made in ten years was not removing this person from the company.

10. Be audacious.  There is a lot of comfort to be had by people getting good jobs and a wariness to take the bold step — but then to have similarly big failures.  What I’ve learned is that failure isn’t the end of the world and in fact, it makes you a lot stronger.  I think that success and ultimately happiness in this world has a lot to do with the spirit of audacity.

Take a moment and think of the people you admire in life.  Did any of them do exactly what the status quo said?  Chances are they didn’t.  Chances are they took big risks.  I believe you have to dare to be great.  Steve Jobs famously said: “When you grow up, you tend to get told that the world is the way it is, and your life is just to live your life inside the world.  Try not to bash into the walls too much.  Try to have a nice family life.  Have fun, save a little money.  That’s a very limited life.  Life can be much broader once you discover one simple fact, and that is everything around that you call life was made up by people who were no smarter than you.  And you can change it.  You can influence it.  You can build your own things that other people can use.  Once you learn that, you’ll never be the same again.”

Similarly, the world needs more people living a life of passion and purpose because living that life inspires others to do the same.  Author/speaker Simon Sinek reminds us, “People don’t buy what you do, they buy why you do it.”  So, blaze a new trail, dare to discover, rely on yourself, take risks, venture further and say yes to adventure.

Lastly, many think that being inside a startup will be a great experience and then people get in and it’s ugly and messy and hard and people aren’t getting along and you can’t figure out direction.  Know for a fact that it’s a sausage factory on the inside and can be psychologically brutal.  But, if you’re called to throw yourself into impossible situations and to seek out problems that require heart and guts to solve, then you have obligation – an obligation not to settle, to spend your days doing your art, to change the rules, to raise the bar and to play a different game.

In the words of Seth Godin, go out at make a ruckus.

I wish you way more than luck.