Time to update your old school expectations

I’ve been thinking a lot about expectations lately and how much they impact our lives. Expectations are a funny thing. They’re rarely front and center in our daily thoughts, but lingering in the subconscious – like an invisible hand guiding our paths (1).

What hit me this morning is expectations can last a really long time… a lifetime if you may.

If parents ensure their child’s chores are completed, the expectation to complete tasks is instilled at a young age. Alternatively if parents set few rules and their children run amok (2), following expectations set outside the home such as appropriate classroom behavior (or later, laws) may be a struggle.

Both positive and negative expectations are likely to follow a child for many years and surely impact a person’s future.

What are expectations

What I’ve now come to realize is someone’s personality and their perceived expectations have a close relationship. Both guide what makes us tick. And both of course impact the way we behave.

It’s interesting to consider that expectations are typically:

A) Set by someone else
B) Undefined
…and because of these
C) Rarely challenged

I didn’t realize until making this list how much influence the expectations of others have on us from an early age. I’m also slightly concerned that I haven’t taken time to define these early expectations, or considered they may need challenging.

Defining expectations

I’ll refrain from sharing an enormous master list of the expectations placed on me since birth, although I do think this would be an interesting exercise. Simply creating an expectations list would surely lend a better understanding of my actions and personality.

I would however like to think more deeply about a few categories of expectations surrounding the work environment:

Employment – most roles start with a bulleted list of activities or results an employee is expected to achieve. V2.0 is setting quarterly KPIs, and V3.0 is OKRs (3). These role activity bullets and associated metrics are typically the extent of employer expectation setting. But aren’t they missing something? What if both an employee and employer specifically listed all expectations they had for each other? I’d guess half of each list would be previously unknown to the other party (4).

Partnerships – In my experience most partnerships fail to deliver the expected outcomes, even though partnership outcomes and KPIs are typically discussed early in the relationship. Maybe what’s missing is an honest discussion about each party’s expectations? I’d guess the outcome of both partners listing their expectations would have the same result of employees doing so – many revealed that were previously unknown.

Rethinking expectations

The core concept that’s still rolling around in my head is that a person’s perceived expectations rarely change. They’re the 500 lb gorilla we’re burdened with carrying, even if the expectation is no longer valid.

Take my wife for example. She was raised in a loving household that expected her to look out for the happiness of others. This upbringing won her the ‘nicest person award’ of our senior class, and to this day she’s a ‘peace-maker’ with an extremely high EQ (5). Probably the best upbringing someone could ask for, resulting in a person who I (and almost everyone she meets) love to be around.

But in some situations it’s not possible to make everyone happy – for example during negotiations or when making tough decisions I’ve seen her and many others struggle to balance the early expectation of delivering happiness when aligning multiple parties around a single outcome. This can weigh on someone and even diminish their own happiness.

There are many similar examples where I hypothesise an expectation is A) set by someone else, B) undefined in a person’s subconscious, and as a result C) the expectation remains unchallenged

Challenge expectations

I could imagine the below 4 steps as a method to consider the difficulties we face and expectations placed upon us:

1) List the past expectations correlated with a difficulty
2) List the reasoning you or someone else used to create the expectation
3) Consider when the expectation was set and how applicable it is to your current life
4) If the initial expectation circumstances have changed, challenge and realign

I’m guessing initially most expectations have some validity, yet over time our situation changes while our behavior remains static. This leaves a need to realign the expectations placed on us (both internally and externally) on a frequent basis.

So what have I discovered? Nothing I didn’t already know 🙂 Circumstances change, and setting aside time to step back and ‘take stock’ is an important aspect of learning and growing as a person.

Remember to stay lean and always challenge the status quo.

(1) Similar to the invisible hand in economics, which describes the self regulating behavior of a marketplace

(2) Yep, I’m pulling out British slang on your ass – don’t run amok!

(3) Ah yes, the new best practice of OKRs – originally created by John Doerr for Google that has taken the tech world by storm. Not familiar? This video is worth watching

(4) It’s worth testing this assumption – I’ll likely make this list with one of my employees next week and report back on how it goes

(5) Emotional intelligence



72 hours to Poland


Don’t judge a book…

As I get older (1) I find myself judging others more harshly… especially during a first conversation. Which is funny, because throughout my life I’ve prided myself on being open-minded and leaving a positive first impression.

Recently with just a few negative signals I have a greater tendency to A) consider the person a moron, and B) try to promptly exit the conversation.

Surely this combination of being quick to both judge and exit hasn’t ingratiated me to some, but subconsciously the time/effort savings outweighs a long and boring discussion.

If I break down my first interactions over the past year they would broadly result in the distribution below (2):

Dislike to like spectrum

The Switcheroo

Something strange has been happening recently. If I interact a second time with someone I initially strongly dislike, I tend to be completely wrong and end up strongly liking them…

Strong dislike to like

Late last year I met a US VC at a European tech conference. Long story short I considered him to be a typical arrogant American and I ended up actively hating his guts.

A few months later I met the same US VC again, spent some 1-1 time getting to know him and his perspective, and ended up strongly liking the guy.

The same thing happened twice recently with people I’ve met in London – a strongly negative first impression, months later a chance second interaction, and now I not only respect the person – but both have becoming good friends!

I hope I hate them?

My complete love/hate flip-flops have occurred often enough that I (strangely) now look forward to a strong initial dislike. Yes some people are jerks I’ll never enjoy. Yet if a high percentage of strong dislikes are likely to convert into good friends, to me that’s a good investment of time.

These thoughts leave me wondering:

1) Is there a correlation between my flip flops and the relationship advice “the more you love someone the greater they can hurt you?”

2) What are ways I can improve my ability to defer judgement and quickly understand someone’s perspective?

3) How does the time between first and second meetings affect my flip flopping?

4) Of my initial strong dislikes, how many also dislike me? And is their feeling toward me correlated with me flip flopping?

Overall the lessons I need to remind myself often are to keep an open mind, continue meeting LOTS of interesting people, and make every attempt to understand the perspective of others.

If you have any advice or tactics on the above, I’m all ears!

(1) I’m 31, so not that old

(2) Despite my increase in harshly judging, I’m lucky to have a positive outlook that still results in a positive impression of 95% of the people I meet.

Blogging for the big picture

Startupbootcamp global team

(above – the Startupbootcamp Global team!)

I’m just back from 2 days of startup CEOs sharing and learning from each other during Startupbootcamp’s alumni CEO gathering in Berlin.Movie A Dog’s Purpose (2017)

It was a great time. Founders Centric led my favorite session about ‘growth hacking’ – which I realized is simply clever ways to gain users without paying for marketing.

The tip from this session that stuck in my mind wasn’t growth hacking specific – it was that growth hacking only works if you find a repeatable process to execute. For example, when creating content (blogs, videos, etc.) Jordan from Founders Centric suggested:

A) Separate ideation and creation into different events
B) Set aside designated times for each activity

Where’s the big picture?

Since joining Startupbootcamp early 2013, I’ve committed most of my waking hours to building the organization. Any free time goes to a combination of being with Tara, exercising, and RumRatings.

Last week I talked with a Startupbootcamp board member about my performance. His feedback was I’ve been executing well and now need to think more strategically about where Startupbootcamp is heading.

For me (and I expect most of us) finding time to reflect and plan is difficult. Since moving to London 4 years ago the only times I can recall thinking about the bigger picture is when I’m blogging.

It’s all about commitment

So I’m doing some growth hacking myself and now twice a week scheduling time in my calendar for blogging – specifically 9am Monday and Friday mornings.

If you can believe it, there are 84 notes piled up in my Evernote folder ‘Blog posts I should write’ – so the content creation part shouldn’t be difficult. When I run out I’ll need to set aside ideation time as well, but for now it’s straight to the writing.

I’m excited to see if writing 8 blog posts this month changes my perspective and strategic mind frame. I know one person asked for automatic emails of my blog posts – so to that person… if you don’t get an email every Monday and Friday for the next month, a swift kick in the ass would be helpful! 🙂

The open job spec

For years I’ve held a core believe that job seekers should apply to a variety of positions, even if they aren’t necessarily “qualified” for them. This isn’t to say a recent grad is ready to become a fortune 500 CEO, but in my opinion most job specs are more malleable than they appear.

From discussing this “malleable job spec” rationale over the years, I’ve observed some are hesitant to apply because of a literal interpretation of the job spec’s wording. They view each bullet point in a desired qualifications list as mandatory – and would be embarrassed if a recruiter thinks of them as silly for attempting to score such a prestigious position.

Reading a post today by recruiter Paul Blumenfeld on VC Jeff Bussgang’s blog helped substantiate my ‘apply often’ hypothesis by saying that “Companies aren’t always clear on what they’re looking for until the right candidate walks through the door”. He goes on to suggest a few methods to alleviate the risk of missing the perfect candidate – including being more open minded and hiring winners who fit the company culture.

The problem is that many potential candidates will still never apply because they interpret the job post literally. Even if the “must-haves” are limited, they’re typically followed by “nice-to-haves” along with a list of position tasks that may dissuade great applicants.

I have a simple suggestion to solve this problem… simply state that great people should apply, regardless if they fit the qualifications exactly. I envision a simple statement like the following would alleviate the concerns of many:

Don’t fit the job spec perfectly but have unique skills that enable you to become a killer (job title)? We don’t hire great backgrounds, we hire great people. If you have a passion for joining an amazing team and becoming the world’s best (job title), we’d love to hear from you!

Including this type of statement would no doubt increases a recruiter’s initial vetting workload, but also has the potential to attract a perfect candidate who isn’t an optimal job spec match.

Has anyone seen a job posting with a similar statement? If so, I’d love to see it – please share it in the comments!

No trust, no sale


Selling is often considered an art form. It takes no less than the most fine-tuned of inter-personal skills and a precise focus on value.

But value is in the eye of a beholder, and to truly sell (I’m told) requires the innate skill to first empathize with a customer’s needs… and then at the perfect moment deliver an optimal solution to their largest problem.

Sales mastery in action

I’ve been lucky enough to witness sales mastery on a few occasions. It was indeed like watching an artist, with a few commonalities:

  • First the groundwork is laid, maybe an initial joke leading quickly to a personal connection
  • Next a mutual commiseration of shared problems and struggles
  • Then the soft touch of a potential solution, delivered ever so delicately at the opportune time
  • And lastly, the close. With the swiftness of a cheetah that somehow leaves the antelope feeling like it won

The ruin of a sale

Someone tried to sell me something today – and it felt all wrong. It simply wasn’t an enjoyable experience.

This bugged me because I was the perfect customer. In fact, not only did I deeply identify with the problem, I had sought out my own solution – which the service I was being sold solved perfectly!. To top it of, the service was FREE and delivered to me on a silver plate.

What was my deal? I had a problem that I unsuccessfully tried to solve myself but couldn’t, and someone was offering me a perfect free solution.

So why did I walk away feeling like a snake charmer just tried to scam me?

Because there was no trust. No groundwork was laid – it was straight to the sell.

The art of trust

Many sales acronyms exist. There’s DIPADA, DMAIC, among others. They’re mostly similar: Identify the problem, present a tailored solution, and close the deal. Some include smaller interim steps such as identifying the key stakeholder and creating time sensitivity – but the main topics remain the same.

What typically isn’t included in a sales process? BUILDING TRUST. Yet developing trust through a true customer connection is the most important element of selling.

Unsurprisingly how to quickly develop a trusting relationship is the most difficult step to teach. Much like delivering a pick-up line… it’s largely an innate ability.

It may involve a simple friendly smile, sharing a story, or keeping a promise. While the tactics may differ, the results are the same.

One of my heros Rand puts it well:

“Best way to sell something:
Don’t sell anything.
Earn the awareness, respect, and trust of those who might buy.”

So the next time you’re selling (we’re all selling something), think for a moment about the personal connection you’ll need to make to build a sale. Without laying the groundwork of trust, you risk coming across as an insincere salesperson to even your most opportune customer.

The interaction of academia and business


I recently met well known author and professor John Mullins – who not only accepted my blind lunch invitation, but was nice enough to invite me to the LBS faculty dining room (best lunch I’ve had this year).

After sharing our backgrounds, the conversation moved to John’s recent research surrounding startup funding and the value of relying on customers for initial cash as validation – opposed to raising angel/VC funds (that’s for a separate post).

I walked away not only with a full belly, but pondering the intake criteria of many startup accelerators and how the industry views initial funding as a ‘proof in the pudding’ milestone.

It really is amazing how one conversation can completely alter your thoughts from a daily task list to the highest strategic objectives of an industry.

It’s hard to believe I didn’t realize until just now how valuable a research-based academic conversation can be… and this is coming from someone with an academic as a best buddy!Watch Full Movie Online Streaming Online and Download

Everyone needs a regular change of perspective, and I for one will be seeking them out much more often. Not only with academics, but people who are generally interesting and willing to disagree with me. But if they do happen to be academics, then hopefully more posh lunches are in my future!

What’s up with mentorship?

I’m a big fan of Bob Cringely’s blog – he’s been a writer in the Valley for years and witnessed the manic rise first hand. Bob recently wrote a post spurred by a student commenting on the lack of mentorship in their home country of Russia.

I rarely write blog comments, but this time felt obliged to share a few mentor/mentee thoughts since Startupbootcamp’s mentorship program is a front-of-mind topic in my daily life.

(my comment posted 14 Sept ’13)

Thanks for the post Bob, I’m a big fan of your blog.

As someone who runs operations for a large startup accelerator group, I’m in essence in the business of connecting startups with mentor’s (and investors, partners, etc). Here’s a few quick things that came to mind from your post:

1) The Russian student’s comment about mentorship being unknown in Russia is closer to the norm globally than you’d think. The US is truly unique from a mentorship standpoint. I’ve found mentorship does exist in Europe and Japan, but far less the US. I’ve had direct experience with mentorship being a completely new concept in many regions – Middle East, Africa, SE Asia. In fact how to tailor our mentor-driven accelerator model to markets outside the US/EU is something I consider on a daily basis.

2) Mentees must seek out mentors, but mentors need to be receptive. There’s no formal application process required – simply seeking advice and asking questions is the key. I wonder how many times the Russian student has sought advice of someone older and wiser? It’s hard to believe if they did their questions were completely dismissed. Human nature is typically more helpful than not.

My guess is a mentor had never directly come to this student with an offer to help, yet the student didn’t realize it’s their prerogative to approach first. Odds are the most successful Russians have mentors because they sought them out, yet proportionately fewer mentor/mentee relationships exist than in the US/EU so the ‘mentorship culture’ has not formed.

3) In my experience mentees have a common trait of considering advice but not necessarily taking it. No mentor wants a mentee who agrees with them all the time… hero worship works for an hour but doesn’t form a relationship. The mentees I enjoy being around not only consider my advice, but have smart responses that make me think. This is why I personally mentor – because I can learn something as well as help someone.

Product first, Business fast

How would I describe myself if raising a funding round? Here’s a typical boilerplate:

“MBA with 5 years of startup operational experience and investment roles with leading accelerator and family office.”

(I know, super lame)

I’ve recently spoken to many-an-entrepreneur with similar credentials. They came from a nifty operations/consulting/banking role, then did an MBA, and are now raising money for the next big thing.

Heck, it’s the “perfect” marriage of hands-on experience with strategic knowledge. But how does an investor view this background? Personally, I only think of one thing: Do they love building products?

Because that’s what tech companies do – they build products. And the best tech company founders I’ve seen are obsessed with their product. They love customer feedback, they’re freaks about metrics, they love lean.Watch Full Movie Streaming Online and Download

Yeah, biz dev/partnerships/managing are all important, but at the end of the day even with awesome relationships if users don’t like your product, you’re screwed.

So, how about this?

“Product-obsessed operations expert, turned investor”

(Still too lame)

Some say their co-founder is an awesome dev. Others plan on hiring a rockstar CTO post-raise. In my opinion, a startup CEO should own their product from day 1. If they don’t, who will?

If this same product-obsessed CEO happens to have a Harvard MBA and came from Goldman/Deloitte/Citi… great! Just don’t let that be the first thing you lead with. It makes you sound like a banker who doesn’t know shit about building a tech product.

So, what’s a super-bright Harvard MBA from Deloitte to do? I call it:

Product First, Business Fast (1)

That’s right, lead strong with your absolute love of product. Make an investor believe all you think of is how to build the world’s best website/app/whatever. On top of that, show how you’ve been honing your product skills – even if it’s just side projects.

If you’re really ballsy, don’t even bring up your sweet MBA/experience. At some point investors will realize you’re better than most when it comes to fundraising, managing, etc. So why even bring it up?

With this in mind, if I were pitching to investors here’s the preferred boilerplate:

“Startup operations junky with a passion for building products and working with entrepreneurs”

All of the above if factually true… I love building products and working with entrepreneurs. Even if it leaves out the MBA and investor roles, who cares – isn’t an initial pitch supposed to spur interest? It’s not like submitting a visa application.

As long as you have a rationale and some backing for the description, I suggest focusing initial investor discussions on your love for building products. Bring up academic record and business credentials later – as a nice surprise after you’ve sold them on an amazing product vision.

(1) Yes, of course this is a take from Mobile First Web Second, Web Second Mobile First,

Viva Colombia!


Tara and I have made our way back to London after spending an amazing 10 days in Colombia. Much of this fantastic experience was due to our friends Juan and Natalia, who graciously guided us through their home country – they were truly the best hosts imaginable.

Juan and I met through my MBA program at Imperial College London. We introduced our wives and quickly realized they were American/Colombian replicas of each other. Unfortunately after school ended Juan and Natalia moved home, but have stayed in close contact.

Considering my knowledge of Colombia came almost exclusively from Clear and Present Danger, I expected our promises of “one day” visiting would be later rather than sooner. After more than a year or broken promises, my Things I’d like to do in 2013 post (which included traveling more) spurred us to finally schedule the trip.

A lasting impression

10 amazing days in Colombia later as we waited to board our flight home, Tara mentioned how interesting it was that most Colombians asked if we were enjoying our trip. This wasn’t the typical “how’s your trip going?” but rather a “we really hope you’re enjoying your time in Colombia, and encourage you to tell the world know how great this place is!”

Encountering so many Colombians who were genuinely proud of their country left a lasting impression. Funny enough, we learned the country’s motto is: “Colombia is Passion.” At first, the saying seemed silly… how can a country represent passion? And maybe 20 years ago it would indeed have been silly; but today’s Colombia is certainly bursting with passion.

They want the world to know their country has come a long way in 20 years. This was surely not the Colombia I envisioned.

Is Colombia the next Dropbox?

An interesting takeaway from my trip has been Colombia’s striking similarity to a promising startup.

When evaluating a potential investment, most investors like to think they employ analytical screening methods. In my experience most due diligence merely validates an initial hunch – a self fulfilling prophecy if you may.

This initial investment hunch may come from a variety of sources – for instance industry insight, but more often than not investors look first for entrepreneurs who are excited to solve their own problem. In essence, they’re passionate about delivering change.Watch Full Movie Online Streaming Online and Download

Passion is infectious, and without it good luck attracting initial employees or raising funds.

If I were evaluating Colombia from an investment perspective, I’d say the signs are all present for a massive return potential. The economy is growing quickly, security has stabilised, and most importantly an army of passionate goodwill ambassadors represent a baked-in marketing advantage.

And the initial traction is already showing. Socialatom Ventures launched in late 2012 and this year Wayra is expanding it’s Latin America efforts to Colombia through a startup and investor summit. Both are supported by a variety of mentors and investors, many that have returned to Colombia after successful startup careers in the US and EU.

With the inherent tourism viral effects in place to spread the “gospel of Colombia”, I’m guessing you’ll soon hear first hand about many amazing experiences like mine in this country. As you can tell, I’m long Colombia and already looking forward to my next trip back.