Startup Lessons


I spend a lot of time with startups and thus hear many companies talk about their approach to sales and their interactions with customers. From these meetings you can really tell the leaders that care deeply about their customers and those the look down on them. Given customers & sales are the lifeblood of any organization you’d imagine everybody would respect their customers. You’d be very wrong.

I was thinking about it this week through some snippets of recent experiences.

Starting with a positive. I had dinner this week with a top new customer at one of our enterprise software investments. I wish I did more enterprise software investing because when I attend meetings like this I realize that this is my core DNA – rolling out business software solutions to customers. The entire dinner was a discussion of what it would take for our software to help this customer be successful, what he liked about it and where we needed to improve. It was a personal discussion and you could tell that our senior leaders and he shared friendship as well as respect and admiration. This was customer interaction at its finest and as a result they invited him to meet with our entire sales staff and offer advice on the sales process from a customer’s perspective. Gold dust.

Contrast that with a VC conversation I had. We were talking about raising money from LPs. He was lamenting how much he hated LP meetings and how little he wanted to interact with LPs going forward. In case you don’t know – as VCs we have have 2 sets of customers: LPs (limited partners) who invest money in our funds and entrepreneurs (who we in turn give money to and help support them in building businesses we hope will be valuable). As an insider I can tell you that a large portion of VCs don’t like interacting with LPs – they view it as a “necessary evil” of the business.

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This week I wrote about obsessive and competitive founders and how this forms the basis of what I look for when I invest.

I had been thinking a lot about this recently because I’m often asked the question of “what I look for in an entrepreneur when I want to invest?” I look for a lot of things, actually: Persistence (above all else), resiliency, leadership, humility, attention-to-detail, street smarts, transparency and both obsession with one’s company and a burning desire to win.

In the comments section a clever question popped up about whether I would have invested in myself before I became an investor.

My first response mentally was, “Of course!” but then I realized I didn’t even need to answer the question. I had invested in myself for years. I quit a very well paid job at Accenture with very little time remaining before making partner and took a risk of having no job security at all. We had raised a $2 million seed round, which meant taking almost no salary so we could afford to hire staff.

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Obsession. The drive to succeed at all costs. When second place isn’t good enough because we live in winner-take-most markets. The desire to be better than anybody else in one’s field.

This blog started from a series of conversations I found myself having over and over again with founders and eventually decided I should just start writing them.It would often make my colleagues laugh because they’d hear me like a broken record and then the next week read my ramblings in a post.

Last week’s obsession was about obsession itself.

10 days ago I saw the film, Whiplash, which is one of my favorite films of the year. I would be shocked if it doesn’t win at least one Oscar. I won’t have any spoiler alerts here, don’t worry.

The protagonist in the film, Andrew, is a drummer and the story is his experiences in his freshman year of one of the most elite music conservatories in the country. He wants to compete to be the lead drummer in the competitive ensemble and study under Terence, an obsessive instructor who is hell bent on winning competitions for the school.

I absolutely loved the film. I loved the music.

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One of the vivid memories I have from being a startup CEO is the feeling that most people in your company have a look in their eyes that like they can do your job as well as you. How hard could it be? You just assign out tasks to all of us.

In the early days the CEO is the jack-of-all-trades, doer-of-all, famously the “chief janitor” or coffee maker. But if you level up, raise capital and grow customers, revenue and staff – life changes. Eventually you need a VP of Product to handle your product roadmap, a CTO for engineering leadership and VPs of sales, marketing & biz dev. Most companies that are scaling have CFOs, heads of HR or talent. The “span of control” for a growing tech startup is probably 6-9 people. The “doers” in your organization.

This is when your job function truly starts to match the definition of “leader” because that’s exactly what your role is. You set direction. You hire great people. You help them prioritize their objectives and review the results. You course correct. You motivate, cajole, reassign tasks, hire, fire and push the organization forward.

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I was at a dinner recently in Chicago and the table discussion was about building great companies outside of Silicon Valley. Of course this can be done and of course I am a big proponent of the rise of startup centers across the country as the Internet has moved from the “infrastructure phase” to the “application phase” dominated by the three C’s: content, communications and commerce. But the dinner discussion included too much denial for my liking.

I think startup communities being simple cheerleaders doesn’t help anyone. Those of us outside Silicon Valley need to make an effort to effect change not just wish for it.

At the dinner some of those arguing that Chicago has everything it needs now that it has built: GroupOn, Braintree, GrubHub and others and that it has “come along way” and “will never get the full respect it deserves just because it’s not Silicon Valley.” But I think this misses the point. I’m a very big fan of Chicago. I started my career at Andersen Consulting (now Accenture) so I went to Chicago many times a year for nearly 9 years.

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We all know that funding markets have changed for startups. The trends are well understood: more angels, more seed funds, more crowdsourcing and so forth. We all can intuit the benefits to founders of these trends so there’s little reason to elaborate. What is less understood are the consequences of these changes.

I have blogged about some of the downside consequences of the changes and the private information I have says the consequences are much worse than is reported in the press since few people publicly talk about

1. How founders get screwed on convertible notes
2. How party rounds can burn you if it takes time to find your groove

There’s another issue I can add to your list of things to be aware of – information rights. Generally speaking in venture capital financings the legal documents will specify that only “major investors” (a threshold set in the agreement – which can be $500,000 investor or more). There is a reason for this.

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