Category Archives: Startups

Leadership lessons from the ancient Greeks – Part I of II

Gates of FireI am a huge fan of the novelist Steven Pressfield. His novels bring the people and events of Ancient Greece to life in a way few others have. He has a particular talent for capturing the essence of war and military life, both its leaders and foot soldiers. His two best novels are Gates of Fire, which tells the story of 300 Spartan warriors sent to defend the pass of Thermopylae, knowing full well they will all perish fighting the Persian invaders, and Tides of War, chronicling the battle between Athens and Sparta during the Peloponnesian War. Each book has an array of memorable characters and has much to teach about discipline, courage under fire, sacrifice and the deep bonds formed between people sharing difficult circumstances.

I want to focus on the two leaders in the books. Leonidas is King of the Spartans and the leader of the band of 300 in Gates of Fire. Alcibiades is the mercurial leader of Athens in Tides of War, until he becomes too powerful and flees to Sparta to avoid being arrested and killed – whereupon he becomes a leader of the Spartans and attempts to retake Athens.  Each is a study of the nature of leadership, its demands, requirements and practices. The chapter in Tides of War entitled “The Intersection of Necessity and Free Will” alone is like a mini-MBA in leadership tactics.

I’ve lived with these books for more than a decade.  They’ve taught me a number of things that have become part of my framework for approaching leadership and management. It’s tough to live up to fictional characters: startups are not war, and companies are not the military. But they share enough key ingredients that they can inform a management style.

I’ve distilled some key leadership principles from the novels.  I share them below, along with some examples of how I’ve put them into practice. There are as many ways to manage as there are managers; these reflect my personal style and underlying value system.  They may not be for you, and I sometimes forget them myself. Some of these work better in larger organizations; some of them are mandatory in startups but harder to make work in a bigger company. In this first post, we’ll look at Gates of Fire and see what it has to tell us; in the second post, Tides of War.

1. Lead by serving.

They could see their king [Leonidas], at nearly sixty, enduring every bit of misery they did. And they knew that when the battle came, he would take his place not safely at the rear, but in the front rank, at the hottest and most perilous spot on the field. [Gates of Fire, p. 69]

I will tell his Majesty what a king is. A king does not abide within his tent while his men bleed and die upon the field. A king does not dine while his men go hungry, nor sleep when they stand at watch upon the wall. A king does not command his men’s loyalty through fear nor purchase it with gold; he earns their love by the sweat of his own back and the pains he endures for their sake. That which comprises the hardest burden, a king lifts first and sets down last. A king does not require service of those he leads but provides it to them. He serves them, not they him. [Gates of Fire, p. 350]

What might this mean in “real life”? People will give you more in effort than you can ever compel, if they believe you care about them and a shared mission. The leader’s job, in the end, is to make sure the objective is clear, and that the team is as productive as possible. This means clearing roadblocks instead of doing “fun stuff”. There are a million menial tasks to getting a startup off the ground and keeping it running. At goby, we keep a pretty good stock of food, drink, snacks, and office supplies. These are my responsibility; every other weekend or so, I drive to a nearby BJs warehouse store, load up on low cost drinks and snacks, and stock the kitchen with them. In this way, I send a message that no task is beneath me, and it shouldn’t be beneath anyone else either. In addition, people who do the real work of building things can spend their time on that, rather than on errands assigned out by the CEO.

2. First to rise, last to bed.

It was the standing order of my master on campaign that he be woken two hours before dawn, an hour prior to the men of his platoon. He insisted that these never behold him prone upon the earth, but awake always to the sight of their enomotarch on his feet and armed. [Gates of Fire, p. 228]

Your team should believe you are as or more dedicated than they are (and you should be!). They should never have reason to question your effort or work ethic – you are a model for them to emulate. While simply being in the office doesn’t guarantee anything gets done, there’s no substitute for your team to see you, day in and day out, working as hard or harder than they are. This is a place where the demands of modern life and the “real world” can clash with fictional or heroic stamina. The demands (and joys) of family, friends, and outside interests can prevent you from being the first one in the office and the last one to leave every day. If you can’t do both, you should pick either the beginning or the end of the day, and consistently be first (or last). My practice is to be first in the office.

And don’t leave your team alone during the tough times. If your people are working weekends, so are you. Long nights too. There may not be anything for you to do, but be there. Do QA, bring food, do busywork, clean the coffee machine. Whatever. You may think this isn’t noticed. It is. At one of my previous roles we were completely redoing the user interface of a ten year old product. It was a massive undertaking and something of a “death march” project. At one point someone came to me to resign; he couldn’t take the demands of the project. But he told me that he really appreciated how I didn’t ask anything of people that I wasn’t willing to do myself. [Note: this isn’t really the way you want to run projects – death marches are to be avoided – but if your team is on one, you better be there 8)].

3. Lead by example.

Simultaneously, work was begun on rebuilding the ancient Phokian Wall which blocked the Narrows. This fortification, when the allies arrived, was little more than a pile of rubble….A wry scene ensured as various engineers and  draughtsmen of the allied militias assembled in solemn council to survey the site and propose architectural alternatives….Leonidas simply picked up a boulder and marched to a spot. There he set the stone in place. He lifted a second, and placed it beside the first. The men looked on dumbly as their commander in chief, whom all could see was well past sixty, stooped to seize a third boulder…With a cheer the troops fell to. Nor did Leonidas cease from his exertions….”Nothing fancy brothers”, the King guided the construction. “For a wall of stone will not preserve Hellas, but a wall of men”. [Gates of Fire, p. 219]

It sounds trite, but really, it’s important, and not that hard. Lead by example – even (especially!) in the mundane things. It’s easy for an organization to become cynical. One of the quickest ways is to have an organization where “the rules don’t apply” to the leaders.

It’s important that your team do things together, and not just fun things. At goby we do the usual, go out for drinks etc. But there’s nothing like handing everyone a hammer and a hex wrench and having everyone assemble their own desks from IKEA on the first day you open a new office. The sore backs, the bitching, the busted knuckles, builds a team like no round of drinks can do. Find ways for your team to share hardship as well as fun, even if it’s mild hardship.

4. Stay in control – your team will react to adverse circumstances the way you do.

This I realized now watching Dienekes rally and tend to his men, was the role of the officer: to prevent those under his command, at all stages of the battle – before, during and after – from becoming “possessed”. To fire their valor when it flagged and rein in their fury when it threatened to take them out of hand…..His was not, I could see now, the heroism of an Achilles….He was just a man doing a job. A job whose primary attribute was self-restraint and self-composure, not for his own sake, but for those whom he led by his example. A job whose objective could be boiled down to a single understatement, as he did at the Hot Gates on the morning he died, of “performing the commonplace under uncommonplace conditions”. [Gates of Fire, p. 112]

If you’ve been managing for long, or been in software for any period of time, you’ve seen the train wrecks. The customer disaster, the release that you can’t seem to finish, the big product launch that’s gone sideways because your site keeps crashing because that big TechCr­­­­unch article keeps driving people to your site. You’ve seen these, and you know you’ll get through it. It doesn’t lessen the urgency, but you know you’ll get through it. That calmness will prevent worse problems. If you’re working with a younger team, they may not have seen these disasters before, or know how to act or react. You need to stay in control, and be seen staying in control. Bark if you need to, but stay in control.

[Leonidas speaking] “You are the elect of Hellas officers and commanders of Lakedaemon, chosen by the Isthmaian Congress to strike the first blow in defense of our homeland. Remember that our allies will take their cue from you. If you show fear, they will be afraid. If you project courage, they will match it in kind….above all, the little things. Maintain your men’s training schedule without alteration. Omit no sacrifice to the gods. Continue your gymnastics and drills-at-arms. Take time to dress your hair, as always. If anything, take more time. [Gates of Fire, p. 225]

In times of stress, it’s important to stick with your patterns. In sports, they say “you play the way you practice”. You should have repeatable, established ways of doing what you do. At goby, it’s agile development, short development sprints followed by a product release. One of the things I was most proud of as goby came to a close was that even as we were weeks away from running out of cash, we were doing our two week sprints followed by product releases. “Performing the commonplace under uncommonplace conditions” indeed.

5. Equal pain for all.

The army was at the Oaks…on an eight-nighter…[the army] had marched out into the high valleys and drilled in darkness for four nights…drilling day and night. No amenities whatever were brought. Conditions are shared by all. [A joke amongst the men]: “What’s the difference between a Spartan king and a mid-ranker?”. “The king sleeps in that shithole over there, we sleep in this shithole over here”. The purpose of the eight-nighter is to drive the individuals of the division, and the unit itself, behind the point of humor. It is when the jokes stop, they say, that the real lessons are learned and each man, and the mora as a whole, make those incremental advances which pay off in the ultimate crucible. The hardship of the exercises is intended less to strengthen the back than to toughen the mind. [Gates of Fire, p. 67]

There is nothing more corrosive to team spirit than a nasty task that only half the company is working on. There’s a particular kind of task that sometimes arises when you are converting legacy code for example, or test cases, where there’s really no way to automate things, or substitute for doing things by hand. In those kinds of situations, it’s tempting to assign those tasks to “QA”, or “junior people” or some similar subset of the team. Don’t. Everybody helps. In one of my former roles, we were converting to a new user interface paradigm. We had literally thousands of automated tests and no way to convert them. Every single person in a very large team (hundreds) was assigned some tests to rebuild or convert (including me). Everybody bitched; but the work got done and done well. Bitching and Camaraderie are two sides of the same coin, if everyone is bitching about the same work.

6. Sometimes you lose; give it everything you’ve got and do it with class.

As the Spartans go to battle with the Persians on the day they will all perish, Leonidas gives a speech. Here’s the end of it:

A thousand years from now, Leonidas declared, two thousand, three thousand years hence, men a hundred generations yet unborn may for their private purposes make journey to our country. They will come, scholars perhaps, or travelers from beyond the sea, prompted by curiosity regarding the past or appetite for knowledge of the ancients. They will peer out across our plain and probe among the stone and rubble of our nation. What will they learn of us? Their shovels will unearth neither brilliant palaces nor temples; their picks prize forth no everlasting architecture or art. What will remain of the Spartans? Not monuments of marble or bronze, but this, what we do here today. [Gates of Fire, p. 356]

Projects fail; startups fail; established companies fail. When we fail, people are watching; our coworkers, potential future hires, potential future investors, business partners, and they are learning as they watch. Unlike the Spartans, when it happens to us, we have the chance to get up and do it again. You’ll be remembered as much or more, for how you fought the fight, than whether you won or lost.

In the next post, I’ll dive into Tides of War, and its treasure trove of leadership strategies. You can find it here.

A week in a life of a startup

Mark Suster wrote a great post on whether the startup life is for you or not. His post really nailed it, particularly around the roller coaster ride that is a startup, and how you really have to embrace the rollercoaster to enjoy it. I had one of those weeks that really reflected that, so I thought I’d share.

Gonna be a great week. Meeting with an old friend in San Francisco, followed by a meeting with a very smart and well regarded entrepreneur-turned-venture-capitalist, that I’ve met with before and like very much. Hoping to meet with a couple of high profile reporters as well. Then down to LA, where I’m on a great panel at a conference, and going to meet with two potential customers to try to close some projects.

Monday. start off the week with a 6am flight out of Boston for the west coast. Up at 3:30am. Ugh. It’s President’s day, a holiday, for normal people, who are off. Oh well, this is what I do. Pick up a USA Today in the airport, our product, goby, is featured with a very positive review and picture in USA Today. WOOHOO! Hard to beat that as a way to start off the week. Reading my email in the airport, my friend’s company needs him to fly to Chicago so that meeting is off. DAMN! Manage to wedge in a replacement meeting the next day with one of my advisory board members; get some great advice and contacts. Reporter meetings appear not to be happening. I think of another strategic partner I should meet in LA and drop a note; meeting looks good.

Tuesday. Get a random mail from someone I know who wants to explore strategic partnerships; since I’m randomly in the area, we get together and have a very interesting conversation. Walk out of that meeting, the venture person I was meeting with has come up sick and can’t make the meeting. All that prep the night before wasted. DAMN! On the positive side, I’m close to the golden gate bridge, no other meeting to arrange on short notice, so I take a walk across the golden gate bridge on a beautiful day, before driving down to the airport and hopping a flight to LA.

Wednesday. Get off the plane, one of the big meetings I have, the person has come down with Bronchitis and can’t meet. DAMN! But another meeting with a potential strategic partner miraculously appears (WOOHOO!) and I squeeze in a very interesting meeting that didn’t exist before I left. My second meeting drops me a note and lets me know he’s had a basketball injury and can’t meet either. DAMN! Then on to my other meeting, which goes well enough but doesn’t result in getting the business (at least yet!). Slog to the hotel through LA rush hour traffic, grab a drink and a pizza, then off to the hotel room to prep for the panel tomorrow. In bed at midnight. Just before I go to bed, get a mail that we’ve been accepted to speak at one of the biggest and best advertising conferences (WOOHOO!).

Thursday. Up at 6. Conference is going well. Meet a lot of interesting people. Panel goes very well, so far as I can tell (WOOHOO!). Somewhat by chance I make some great connections and have some great conversations with my co-panelists that may help the business very shortly.

Friday. Get a call from one of my colleagues, a deal we’ve been chasing and was looking dicey, we now have what looks like an agreement. WOOHOO! First deal this quarter and couldn’t come at a better time. Get a mail from one of my other colleagues 30 minutes later. Google’s changed their algorithm and punched a huge hole in our search traffic. DAMN! Hop on the plane, and miraculously, the seat next to me is empty so I have some breathing room for the first time in like 10 flights (WOOHOO!).

That’s the roller coaster for the week. A lot of weeks are like that. Big highs followed 30 minutes later by big lows. If that sounds like fun to you, you belong in a startup!

Judging the MIT Venture Capital competion, and, Term Sheet Basics

I’m very excited to be a judge in the MIT Venture Capital Competition tomorrow. This competition is the inverse of the MIT $100k Entrepreneurship Competition. In that event, MIT’ers present their business plan / startup ideas, and the best potential company wins. In the Venture Capital competition, MIT’ers play the role of Venture Capitalists. The judges aren’t selecting the best company, they are selecting the best nascent VCs. As an entrepreneur, being a judge of that is a delicious irony 8).

As part of the warmup for the event, I gave a talk last week on the basics of term sheets. The subject is very well covered on the web, especially Brad Feld’s series of blog posts and on Venture Hacks, and most of material is loosely based on theirs – I include it here in case a summarized overview is useful.

The real problem with Quora

There’s been a blizzard of social media chatter about Quora recently. Robert Scoble loved it, then hated it. Vivek Whadwa doesn’t get it. Arrington thinks Scoble’s nuts. All of this is focused on whether or not Quora is a great blogging platform, how the voting system works, and so on.

Here’s the real problem with Quora, and why it’s going to struggle, until it solves it.

There’s no information architecture. It’s just a huge pile of unorganized content. The value in a Q&A service is the ability for people to process the answers and find useful information, or at least predict where they’re going to find this information. Hunch suffers from a similar problem – it’s hard to know which ‘Hunch’ is going to answer your question. Until Quora finds a way to put some normalization onto the questions, the pile is just going to get bigger and harder to sift through. And this normalization is a hard problem, particularly for subjective questions, which is what currently predominates in Quora. It won’t be an easy thing for them to fix. Wikipedia (to which many comparisons are made relative to Quora) has a pretty clear information architecture, and a dis-ambiguation mechanism, and it’s data model elements are primarily (simple) nouns (Places, People, Topics) – whereas Quora’s primary content are usually (complex) subjectively phrased questions.
Continue reading The real problem with Quora

When to hire a designer (hint: now!)

I’ve been to a few startup events recently, in particular the Future M Startup Bootcamp and NEVCA office hours at Venture Cafe. Thanks in particular to Venture Cafe for hosting the event – it was a great time and lots of good discussion.

A subject came up repeatedly at both events that I think is worth commenting on. The question is, “When should I hire a designer to work on my application/startup”?

Especially for consumer web companies, my answer is, “you should have already hired one”. A strong designer should be one of the first people you hire into a company, for a few reasons. We did this at goby and the company would not be the same if we had not. But before we go into the reasons, let’s talk about what I mean by a designer.

The word “designer” can mean a lot of different things to different people. There are graphic designers, web designers, product designers, and a number of other variations in skill-sets and perspectives. Product design is not about having a cute logo (although that helps). It’s not about having good fonts & colors (although this is a good idea and harder than it looks). It’s not about having a clean and elegant user interface (although that’s becoming an expectation if not a requirement in today’s consumer web environment). It’s fundamentally about understanding your customer – a good designer is always thinking about who your user is, why they’re coming to your site, what they think they are seeing when they see your site for the first time, what your information architecture is, and how they are going to react to all of it. They will also be well versed in what’s going in the outside world, what trends exist in design, and why those trends are happening. They’ll also be out talking to customers, getting feedback, and incorporating that into their designs.

Expectations are insanely high in the consumer web. People make instant, instinctive judgments about the value and trustworthiness of your site. This isn’t just about good graphics, it is deeper than that. And if you don’t get it right, you’ll struggle to find and keep visitors.

Ideally, you would find someone who can also do web/graphic design and wireframes as well, but if all you want is a nicer looking site, you can find a contractor to help with that on an as-needed basis. But this misses the point. There’s a natural tendency for product developers & engineers to design the product (and they should be intimately involved of course!), but there is deep benefit in having someone who is outside the coding process thinking about users from their perspective, and without being too tied to the engineering process.