Forming an Advisory Board that’s not horrible

In my last monthly company update for Hitlist, I asked for advice on how to form an advisory board. Here’s a distillation of the feedback I got.


  1. Not too early. “Advisory boards are super helpful (and cheap) if done right, and an expensive (in equity) waste of time if done wrong.” – Josh Elwell, a partner at ValueStream Labs, a FinTech accelerator. “Asking someone to become a formal advisor in the early stage of your company’s growth might be overkill. You can gain many of the same benefits through lunches or phone calls every couple of months – something most can commit to.” – Kerrie MacPherson, Principal, Financial Services Office at Ernst & Young (h/t to Betsy Mikel of Women 2.0 for pointing me towards her post).
  2. If you’ve raised an angel/seed round without a lead investor. “The problem and the challenge with not having the board after the Seed round is that there is no outside, non-executive perspective on the company. There is no higher level accountability for CEO, there is no regular milestones, and no regular check-ups… great boards help keep the business healthy and help accelerate it” – Alex Iskold, managing director of TechStars New York (h/t to Brittany Laughlin of USV for pointing me towards his post).


Via Chris Thorpe, director of engineering at EMC:

  • Advisory board members are people who can either make introductions to key people (former travel executives, for example) or solve hard problems but you don’t need them full time.
  • Ideally look for people who have been on “real” boards and/or have been CEOs or C_Os of companies that you admire.
  • I see executives hire “big names” to advisory boards and it looks good on your website but if they never read your emails or make intros then it’s just marketing. So you should reference check people.

Via Tim Peek of Peek Disruption:

  • While it’s important to have people in your industry on the board, I also believe that diversity of thought and experience is even more important for a disruptive player like Hitlist. So, I’d look for people in “adjacent” industries — areas of business that share some attributes with the travel industry but also are different or perhaps already experiencing what you hope to create in travel. What other industries have followed a trajectory similar to the one you hope to create in travel? Look for people from there to advise you.
  • Culture. I do think culture is the major differentiator for businesses in this century. In my experience too many startups are solely focused on execution (makes sense – there is a lot to do, not much time, and not many people to do it) and culture grows unnoticed. They end up with cultures that ultimately are unsustainable — I believe this is why so many startups don’t survive or have a deep “sophomore slump” and can’t come up with an effective 2.0 product or strategy once they are off the ground. So, what businesses have cultures which are successful and which you want to emulate — get those folks on your board.
  • A leadership advisor specifically for you. Someone you believe can take your leadership to the next level, support you in finding solutions to tough questions, and help you keep your head above the rising tide of daily business to focus on the big questions and direction.

Again from Josh Elwell:

  • Try to get at least one person who is “friends” with lots of people you want to know (investors, partners, customers, etc). Warm introductions are valuable, but that person pushing on “friends” from behind the scenes is even better at getting things done quickly.
  • Try to get at least one person with a “big” exit who fully understands the strategic process of getting a business sold (the second part is critical, because lots of entrepreneurs were lucky, not strategic). I get the best advice from people like that because they think about the end goal and how little decisions made now can help later.
  • Those might be the same person.
  • Relevant industry experience is nice, but I find that people with it aren’t as helpful as I had initially expected if they don’t have 1 and 2 (apart from just using their names for credibility).
  • I have an advisor who used to be a senior level management consultant. He is super helpful with lots of stuff even though he doesn’t have 1, 2 or 3. He always asks the right questions, cleans up all our pitch decks with ease, and is just generally a great person to get rapid feedback on new ideas.

Again from Alex Iskold:

  • Include 2-4 people plus the founders.
  • Recruit one or two of your top angels + other experienced operators/mentors.


  1. Commit to talking to each board member every 4-6 weeks and meeting with the whole board every 2-3 months. People can dial in if necessary, but in person is ideal.
  2. “Don’t be afraid to swap folks out if it turns out to not be a fit.” – Iskold
  3. Set clear expectations for commitment. “Board members will only rise to the level of performance articulated to them and expected of them, so as a board, it is important to clarify expectations with potential new members from the beginning.” – Sarah Najarian and Caroline Page of Robin Hood (h/t to Betsy Mikel of Women 2.0 for pointing me to their post)

More from Thorpe:

  • Grant up to 2 years for your advisory board’s stock grants (typically 10–25 basis points, in my experience, depending on their contribution and experience), but then have it renew by mutual agreement every quarter and vesting happens quarterly. If someone isn’t helping you or they get busy, then you simply don’t renew them for the next quarter.
  • Building the right culture around your board is paramount and it’s one of the things that’s really hard to do when you’ve never done it before. In my opinion for a new CEO, it’s ideal to have a friendly “chair” who can help you manage the rest of the board. This is ideally a former CEO who shares your cultural values, is busy with other things, and doesn’t want your job.
  • Practice building your communication skills with them, talking about issues, presenting company strategy, cash flow, income, creating a plan and showing your progress against the plan (and how the plan evolves over time – it’s a startup, not a public Fortune 500 company). Make a habit of calling your board members in advance of your meetings and making sure they understand what’s going to happen and that you have a chance to answer their questions and address their concerns.
  • At some point investors will want to take a board seat or have formal board meetings. That’s why it’s important to have already established strong relationships and board culture that work well for your company, so that your existing board members can keep meetings in line with that culture. Culture helps prevent unproductive habits like board members ordering you about what to do, regularly showing up late, talking directly to your employees, or going “off the ranch” to others outside your company. A good maxim is “eyes on, hands off” (or “fingers out”). And you kind of need to see people in action for a while before you know. Do they support you as CEO in the board meeting and prepare you ahead of time with their issues? Do they seek to support you when bad things happen, or do they surprise you in the middle of a board meeting with a hostile question? Do they work through you, not around you? Do they ask you hard questions that make you defend your decisions and understand your assumptions better, even if you don’t change your mind? Do they respect your deep understanding of the landscape more than their own brilliant insight from 30,000 feet? Etc.
  • Board meetings can turn into a lot of work, so try very hard to limit the amount of work to just the amount needed to keep you accountable and get strategic and tactical advice. I’ve seen a lot of startups spend way too much time preparing detailed analyses and predictions on the basis of data that are too limited or early stage to be of much predictive power. Understand what you can reasonably know and not know, and what you can reasonably predict from that knowledge. Don’t be afraid to say “this is the best we can say given what we know today, and we’ll update it as we learn more.”
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I recently noticed Blogspot has a new ‘stats’ feature that allows the blogger to see how many people are visiting the website and what brought them there. Among the search terms that will bring you to Gill Morris’s blog are:

buying marijuana in Istanbul
dating a Ukrainian man
Christians in Dongguan

I think this would be excellent material for the next time I play two truths and a lie.

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A Greenwich Citizen

As I’m sick of being harangued by the one or two people who actually read this blog about the lack of posts over the last month, I’ve decided to make like a real writer and recycle old material. I’ve been writing a biweekly column for The Greenwich Citizen, a local paper from my hometown, since the beginning of August. If you can tolerate the odd bit of Greenwich arcana, please click the links below for a fresh take on some old places. I’ve tried to insert them in more or less chronological order – apologies for the occasional redundancies.

Go East, Young Woman, and go Crazy with the Country

Dear, Dirty Dongguan

Spot of Golf, Genghis?

O Sad Siberian Night

The Bush-Ahmadinejad Connection

A Country to be Proud Of

Everyone Should Have Experience

(Actually, I have no idea how many people read this blog. At least two, guilty of mentioned haranguing. Please feel free to email or comment to let me know you’re reading – I’d love some feedback!)

Also, here’s pretty picture of the Basilica Cistern, in Istanbul’s old city, because everybody likes beautiful pictures:

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Turmoil or in turmoil?

A new dimension of hilarity was added to my job search when I discovered Reuters-sponsored AlertNet.

A fantastic website, a noble cause, but who decided which euphemisms to use? Choose one under ‘Filter by Emergency’:

Afghan Turmoil
Chad Troubles
Iraq in turmoil
Nepal Peace
Thailand Violence
Western Sahara dispute
Very Intense Tropical Storm Hamish

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Gillian in China, the second time

I flew into Hong Kong under a typhoon warning. I expected drama when I arrived, but the air was perfectly still. The white birches lining the hallway seemed somehow sepulchral. There is nothing so terrifying as the calm before the storm.
It didn’t help my feeling of unease when, at the border, a Chinese official wearing a mask pointed something that looked very much like a pistol at my head. Apparently, he was measuring my temperature in an effort to make sure that no one with swine flu made it into the country.
The typhoon never materialized.
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The future, Part I

I’m a senior in college. Many of you will be at some point and more of you have been already. This is the year that decides the rest of your life, or so at least many of my classmates seem to think. Realistically, with the average American changing careers 6-7 times during the course of their adulthood, whatever my peers and I end up doing next year is not necessarily make-or-break. 

Even with this in the back of my mind, however, I got swept up at the beginning of this year in ‘e-recruiting’, also occasionally, affectionately known as selling one’s soul. E-recruiting is the name given to the process wherein hundreds of Harvard students are wooed by firms that intend to offer one or two spots (maybe) to students, who go on to fame and fortune – really just the latter – in the world of finance or consulting. I half-heartedly applied to some firms and then started looking into grad school and fellowships.  

It’s been kind of fun. I recently turned in an application to follow the steps of thousands of pilgrims on the Camino de Santiago, the pilgrimage route across France and northern Spain to Santiago de Compostela; ostensibly to study the motivation and religious convictions of modern-day pilgrims while cleverly incorporating the knowledge gained from my medieval history courses and language study here at Harvard.

And then a few weeks ago I went to morning prayers, a fifteen minute service held at 8:45 every morning in Memorial Church. Other than a hymn and a closing prayer, it’s not much of a religious affair. The centerpiece is always a speaker, unreliably Christian, who gives a short homily about work, life, baseball, whatever.

I always mean to come more often, but I suffer the delusion that I will get something incredibly important done during the same time period (usually sleep).  Anyway. The talk of the morning was about being mindful of the world’s poor: about how a mosquito net which can save a human from malaria costs less than two coffees, if we would only take the time to send the money in the right direction. 

These are logical points, and they are ignored on a regular basis. In the midst of e-recruiting and fellowship-applying, it was easy to forget how using Harvard’s money to fund a joy-trek across northern Spain might not be the best way to ‘give back’.

Of course there are different ways of doing our best for the world. I’m not condemning the idea of looking for spiritual fulfillment or suggesting that every college senior should do Teach for America in Mississippi or build canals in the African desert. People have different strengths, and the way to best serve the greater good of humanity – or God, if you like – is going to be different for every individual. Maybe, on said trek across northern Spain, I’d gain cultural insight and language proficiency that would allow me to make better informed decisions in a future job in the US foreign service. 

It’s easy for those of us who are studying: we can glorify the stuff we do every day as contributing to our future usefulness.  And those of you who teach are surely helping us. And those who work to make this University community such a good place for fostering intellectual and personal growth are likewise performing a valuable service. 

I could go on. Anyone who does any small thing to make the world go round is serving the greater good. A father who drives his kids to school is taking time to raise his children well, which is for the greater good. The dining staff who check our IDs at the entrance of the dining hall to make sure each hall is allotted the right amount of money – is serving the greater good. 

The difference is in the degree. Maybe that father could be better serving the world by having his kids ride the bus, saving the gas money, going to work earlier and coming home earlier to spend time with his kids in the afternoon. Maybe that dining hall ID checker could be inspiring freshmen to be a better person like Domna over in Annenberg. Maybe I could spend next year challenging myself by teaching in rural Mississippi. Maybe each of us could have two fewer coffees and buy a mosquito net. 

Simply put, it’s not enough to be doing well if we have the ability to be doing better.  It’s not enough for ourselves, it’s not enough for humanity.

I have no wish to discuss my own religious beliefs or lack thereof on the internets, but Sir Francis Drake wrote a poem in 1577 that I’ve always found moving:
Disturb us, Lord, when
We are too well pleased with ourselves,
When our dreams have come true

Because we have dreamed too little,
When we arrived safely
Because we sailed too close to the shore.

Disturb us, Lord, when 
With the abundance of things we possess
We have lost our thirst
For the waters of life;
Having fallen in love with life,
We have ceased to dream of eternity
And in our efforts to build a new earth,
We have allowed our vision
Of the new Heaven to dim.

Disturb us, Lord, to dare more boldly,
To venture on wider seas
Where storms will show your mastery;
Where losing sight of land,
We shall find the stars.
We ask You to push back
The horizons of our hopes;
And to push into the future
In strength, courage, hope, and love.

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Sex, Politics, and Football

I’m working in Spain this summer, but I flew to Paris, where I used to live, to get a cheaper transatlantic flight and to catch up with old friends. I met one in the Marche St Honore, a quaint square not far from the Avenue de l’Opera which had an alarmingly modern glass brick of a building in the middle. 

She and another friend, Caroline, had just seen ‘Definitely, Maybe’, a ‘chic-flic’, to console Caroline, who has just broken up with her boyfriend of two years. After briefly discussing our personal lives, Caroline turned to me and asked ‘Alors, tu adores George Bush?’ She went on to explain that she fancied herself the only libertarian in France and that, while she disapproved of Bush’s spending habits, foreign policy, actually his entire administration in general, she saw a lot to like in the American Republican party.

I said that she must, then, be happy to have Sarkozy, practically a libertarian by left-leaning French standards, in the Presidency. She gave me a withering look and I was reminded of the fact that I have yet to meet a French person who has expressed any faith in the political system. What did she think about Europe, then?, I asked. And the Lisbon Treaty, which the Irish so recently blocked by voting against it in their national referendum? (The EU, still lacking a Constitution – the draft proposed in 2005 failed to pass referendums in France and the Netherlands – takes as its legal code a succession of treaties, the most recent of which is the 2001 Treaty of Nice). It would never pass, she said. 

The way she sees it, Europe is doomed to a future of lukewarm alliances between semi-hostile nations who nevertheless realize they have more in common with each other than the rest of the world and therefore will accept small compromises, but only after exhausting every effort to demonstrate they would rather not. Like, for example, the Irish, who will eventually accept some version of the Lisbon treaty, most likely almost identical to the one 53% of them just rejected. In sum, Europe can look forward to a future as full of exasperating negotiations as the last 50 years.

Tiring of politics, the discussion moved on to football. Not to make any gross generalizations, but I’ve found that many of my conversations in France follow this basic pattern: standard greeting (a kiss on each cheek), inquiry into the personal life (do you have a boyfriend?), discussion of politics (plus ca change, toute c’est la meme chose), and, finally, football. 

Spain beat Russia in the semi-final for the quadrennial European Cup and will be playing Germany tomorrow evening. I mentioned how frustrated I was with myself for having bought a ticket for the overnight train from Paris to Madrid for Sunday evening and therefore unwittingly ruining my chances to see this potentially historic event with the Madrilenos. Two years ago, I was chaperoning a tour in Italy and we found ourselves in Rome the night Italy won the world cup. After putting my charges to bed with dire warnings about how dangerous the streets would be – full of drunk soccer hooligans! – a fellow chaperone and I put on as much azure (the color of the Italian jersey) as we could find and hit the streets. 

The scene was, as one might predict, absolute bedlam. Thousands of mopeds and Peugots with twice as many passengers as they should normally hold were packed bumper-to-tire along the avenues. Blaring horns competed with flag-draped and beer-soaked revelers chanting ‘Italia!’ and the opening lick to the White Stripes’ ‘Seven Nation Army’, which I later learned is the theme music played on TV before soccer games. I’m not a fan of professional sports and you could not pay me to watch a Red Sox game on TV, but I’ve had quite an affection for European soccer matches since that evening.

‘I wouldn’t worry about it,’ my friend said with a wink. ‘You won’t be missing anything. Germany is definitely going to win this one.’

Reassured (falsely), I said goodnight to my friend and met a friend from Harvard who wanted to go dancing. One thing led to another, and we found ourselves watching the sun rise over Paris from the steps of Sacre Coeur with Nick, a rather drunk American serviceman on leave from Baghdad. 

Sitting among the glass shards of wine bottles left over from others’ Saturday night revelry, I asked him how long he had before he went back to Iraq. ‘I’ve been stop-lossed,’ he said. ‘Do you know what that means?’ I replied that I wasn’t sure, but from what I understood it meant that soldiers who had served their time were sent back overseas rather than discharged. ‘Exactly,’ he said. 

I didn’t press him on it, but I’ve been wondering a lot about the policy recently. According to Wikipedia, ‘Stop-loss’ is ‘the involuntary extension of a service member’s active duty service under the enlistment contract in order to retain them beyond their initial end of term of service (ETS) date.’ When servicemen enlist, they generally sign a contract obliging them to a fixed term of 2-4 years. In the fine print, however, is the catch: ‘the President may suspend any provision of law relating to promotion, retirement, or separation applicable to any member of the armed forces who the President determines is essential to the national security of the United States’ Title 10, USC Section 12305(a). Challenges to the legality of the policy are, therefore, difficult, but challenges to the moral rightness of sending those who have already put their lives at risk for their country back into the combat zone involuntarily are gaining ground, no doubt aided by the recent movie ‘Stop-Loss’ and the general discussion provoked by our upcoming election.

I turned to hug Nick, in a completely inadequate gesture of sympathy for his situation, but found he had wandered over to a group of French 20-somethings in order to bum a cigarette. They asked him what he thought of the war in Iraq. He drew his eyebrows together in a look of extreme concentration for a moment, shrugged his shoulders, and said, ‘It’s heavy. Shit. It’s heavy.’

Not knowing what to say, we watched the rooftops turn from dark gray to silver. My father once pointed out how, in the early morning twilight, it always seems like the sky is as bright as day, and then the sun actually appears and it’s hard to hold back a feeling of utter joy and contentment with the world. I’ve always found it to be true, no matter what is on my mind, and this morning was no exception. I wonder if it worked for Nick.
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