Customer Zero Gets Wrinkly

What do most company founders dream that they’ll be doing in 27 years time? I’ll be 64… Will you still need me, will you still feed me?

I imagine most dream they’ll either be running their business in some fantabulously successful form, or having exited for some stupendously pocket-bulging amount of money and lying on a yacht in the sun somewhere.

Neither interest me.

Before my investors do a run on my company’s piggy bank, I’m not suggesting that I don’t want Wholi to be successful. Instead I really, really want to use what we’re building in 27 years time. I sincerely hope we (or someone else) has built it.

My team sometimes call me ‘Customer Zero’ at Wholi when we’re trying to design the product – and I make no apologies about focusing the company on building something I really want. Maybe CEO is just short form for CustomerzErO anyhow?! As Paul Graham states, the key to success is to ‘build something people want’. This isn’t an ego thing, but instead our hope is that if I want it, others will too. It’s how Google and Apple started and they’re doing OK.

People search has fascinated me for a long time. The reason is that all the best things I’ve experienced – from the boardroom to the bedroom – have happened as a result of meeting amazing people. I believe that when two of the ‘right’ extraordinary people find each other at the right time, the outcome can be a million times better than when two of the ‘wrong’ people find each other, when there’s a mismatch, or even then there’s a sub-optimal match. Think Larry and Sergei, Steve and Woz to use the companies above – examples of what can happen when two amazing people meet. Universities or communities are a useful proxy for bringing the right people together, but I believe it can be done oh so much better.

We’ve taken a few twists and turns along the people search journey and, no doubt we’ll have a few to come. Yet the essence remains true, which is that Wholi is focused on trying to enable the right people to find each other.

So what do I want, when I’m 64?

My dream is to be able connect the right people… lazily.

Said another way, I would like the people I know who have a problem or opportunity to feel totally comfortable and easily be able to ask me for help. Then I would like to be able to connect them with another person I know who would be able to help them. Preferably the best person possible to help them. And I’d like to be able to do this in seconds.

I’ve mentioned before that I don’t think LinkedIn can achieve this vision any more, even though that’s what they set out to achieve. Yet it’s founder Reid Hoffman is a role model for this mode of being. I read somewhere that he aims to sit at the intersection of networks, being helpful to people in order to get stuff done. I paraphrase from my memory as I’m writing this on a plane, so I hope this isn’t a total misquote or misattribution, but I believe he does this supremely well.

As for me, I’d like to be able to be somewhere far away – say Kenya (perhaps my favourite place) and yet be able to connect 10 people who should meet each day and create significant value by bringing them together. I want to do this in a short period of time, so that I can get on with doing more introductions, or do something else like kitesurfing (hopefully I’ll still be going aged 64). I don’t want technology that forces me to look at a screen for longer please! I don’t care too much if I get something out of these connections. Some people paint, some write music – for me this is a form of creativity that gets me out of bed each morning.

It’s not wholly altruistic, by knowing who to ask for help, I hope to also get things done, come across new exciting opportunities meet amazing people. It would be a reason to meet new people and to continue to network, rather than the vanity networks we have today.

Whether someone in need is looking for a new therapist, kiting buddy, or an entrepreneur has an idea for a company, or a friend needs help with a legal issue – to be able to direct them to the right person to help them would, for me, be wholly fulfilling.

That’s what we’re trying to build today with Wholi – do come and try it out. I’m also helping as many people as I can for 50 days so please do ask me for anything you need.

Here’s to being needed (and fed) when I’m 64.  

64 candles is more of a bonfire with a cake on the bottom…

Control Your Asks

Alongside our 50 Days of Help campaign, we’ve had a fun few weeks putting the new Wholi app through its paces with some early users. Our mission is to enable people to ask their network for help more easily (and help them back). Here’s our earlier post on why we think networks on places like LinkedIn are ineffective.

We’re loving working on this problem and it’s beginning to work! The Wholi team is more excited than ever which is resulting in strange outbursts on our internal Slack channels:

As we’ve learned more and more about how people ask for help, we’ve made significant improvements to the app and just released a new version which you can find on

Here are some of the new things we have included in the shiny new app we’d love you to try:

  • Rather than asking everyone you know on the app, you can now select who you send your asks to, meaning it’s no longer an ‘all or nothing’ approach re: who you get help from. This will enable you to target requests to the right people
  • You can now make more than one ask, in case you’ve got a number of things you need
  • If there’s someone who’s asked for help and you might know people who can help – you can now forward on their asks to people in your network.

We’ve also learned that one of the principal problems is people are reluctant to ask, or don’t have enough contacts on the app yet, so, firstly, do invite a few people, it’s surprising how easy it becomes to help your network. But we’ll also be focusing on making it easier to know which asks are most likely to get results. Coming soon to a screen near you.

As ever, we love feedback so if you’ve any thoughts or suggestions do get in touch. Plus do ask Tom if there’s anything at all you need help with. Onwards.

50 Days of Help

In the next 50 days, I am going to go a bit bananas and go on a helping spree. My aim is to solve professional problems people have, by introducing them to someone I know that might help. My aim is to do this as much as I can in the 50 days.

See my previous article – ‘Just Ask’, which explains why I’m doing this. 

Here’s how it works:

  1. Don’t be shy – PLEASE DO ASK or I can’t be as helpful as I’d like to be…
  2. It should be a professional problem you have that could be solved, or helped by one person in my network – so I should be able to help in <10 mins.
  3. Email me at tom at wholi (if you can’t guess the rest, I’m not sure I can solve your problems!) with a simple, “Know anyone who XXX in order to solve YYY”.
  4. Here’s me on LinkedIn if you want to see what I’m likely to be able to help with
  5. I want to be able to determine who’s best to connect you to, so don’t ask for specific people
  6. I will only intro you to someone if I think they want to hear from you!

Some examples:

– Know anyone who knows about ‘transparent salary’ schemes?

– Do you know a good business coach in London or Bristol, I want to learn X?

– Know any angel investors in London who are interested in AI, we’re looking to raise X?

– Do you know anyone who might be willing to sit on our board, specifically someone with X skill?

– Know a good product consultant to solve X?

I won’t help with things like, “I need a software engineer”, or “do you know anyone who wants to buy my product”. It should be something that one person in my network can help with.

…and some guidelines:

  1. This isn’t about achieving a maximum score. I want to focus on quality, not quantity. I’m not going to stay up all night, take class A substances to keep me awake or skip holidays. I am going to try my best to be helpful within ‘normal working hours’, where I can.
  2. Don’t ask me to connect you with specific people e.g. I see you know X, can you connect me.
  3. I’m not going to sell stuff on your behalf, or persuade someone to join your company. Use your judgement. 
  4. If I don’t respond, I probably can’t help. I will do my best!  
  5. The aim of the experiment is to maximise the help I can give. If it ends up being shared, we get press, or people want to sign up to Wholi because they want to help more – so be it, but that’s not the aim. The reason why we want to expose this campaign is simply to maximise the help.

I’ll do my best to share the journey as well my findings/learnings and thoughts as I go.

Thanks for helping me help! 

Just Ask

I’ve had a bit of a Damascene moment recently, which I wanted to share… plus it has also prompted me to run an experiment to see how many people I can help in 50 days (more on this here).

I have a moderately good network and take great pleasure connecting people, meaning I absolutely love introducing people who can be of mutual benefit. Yet I’m also a busy person who wants to get shit done, so I’ve tended towards helping people with an expectation – when there’s obviously or potentially something in it for me. It sounds selfish put like that, but like most businessmen, I’ve wanted to be rewarded for my time. Whether consciously or subconsciously, I’ve traded favours.

My Damascene moment has been to realise that by unshackling myself from an expectation of return, I can be way, way more helpful and that – perhaps ironically – means I’m better rewarded.

The realisation is certainly not my own – I’ve been prompted by articles such as this, and much wiser, more experienced people like Reid Hoffman, Adam Rifkin and Naval Ravikant, to name but a few.

There is no Machiavellian hidden agenda. This is not pure altruism, but instead a realisation that there is a beautiful symbiotic benefit in being as helpful as possible. I still want to get things done, but this approach of helping without expectation actually helps me get more done and is distinctly more pleasurable. I’d rather not try to calculate whether this or that introduction has a certain value but instead just maximise my ability to help (knowing that it was valuable to both parties involved, of course).

Perhaps years in a boarding school initiated my tit-for-tat survival strategy, because whilst this is a painfully simple idea, it’s actually been remarkably difficult to execute. There’s a fine balance that’s hard to strike. Some people excel at this, but most, myself included, do not. Too often when someone has come to me for help and I’ve slipped back into my old mindset of feeling time-poor, or unwilling because I can’t see the value. Like a meditation practice, I’ve had to keep bringing myself back.

The second issue preventing my help campaign is that people don’t just ask. In hundreds of chats, I’ve learned that people are reluctant to ask for favours because it feels awkward, they don’t want to be needy, or they don’t know who to ask either based on their knowledge or who will help. They ask close contacts because of that discomfort and because it’s easier to ask those they feel comfortable. This in turn means that it’s actually quite hard to help people at scale, because it’s hard to figure out who needs help with what. I’ve scoured Facebook, LinkedIn and groups that I’m part of to try to find what people need – yet people don’t ask that often. Or when they do on a public forum, it’s desperate, or a request of a certain kind that can be dealt with publicly. This makes it it tricky to be helpful.

So with a view to helping out more often, I’ve begun an experiment. Starting on the 8th May, I want to try to help as many people as I can in the next 50 days. More on that here in a separate post. Please don’t hesitate to ask me for help by email (tom at you know the rest).

Please do JUST ASK… Here’s how I see it working – if you’ve a professional problem you have that could be solved, or helped by one person in my network, I would love to know about it. It doesn’t matter you and I know each other and I certainly don’t want anything in return, except to learn and maximise my ability to help. Because, as I’ve learned, it is the process of helping and bringing people together who can benefit each other that is most fulfilling, the rest is a bonus.

Vanity Networks

They say it’s not what you know, but who you know. But who do you know? What does knowing someone mean today?

We’re taught that it’s wise to build our personal networks – it’ll make us more successful knowing and being connected to lots of people – and technology now aggressively encourages this behaviour. We now live in the ‘Networked Age’. Even the most introverted misanthropes can now acquire a plethora of connections using various social networks.

Like many entrepreneurs, I have a mere 5k+ connections on LinkedIn and 1k+ friends on Facebook. These are my ‘professional’ and ‘personal’ contacts, as defined by these platforms, which claim to help me stay connected. Yet what does being connected mean? Who is actually ‘in’ my network and what can I do with it now that I’ve built it?

There’s something fundamentally wrong in the way existing technologies suggest we acquire contacts, with a focus on quantity not quality. These connections belie so many different types of relationship, past histories and experiences that they’ve become superficial, noisy and hard to navigate. In the modern rush to embrace connectivity, we’ve become so fixated on broadening the number of people we can reach that we’ve forgotten the reasons why we connect in the first place.

Surely the only true reason to build a network is to be able to use it effectively, rather than simply to have it? If it’s hard to use your network efficiently then it is somewhat useless, no matter how big it is or how many important people are in it. Most people have ‘vanity networks’ – to butcher the term vanity metrics – meaning large numbers with little substance. Ironically, the larger the number of people in a network, the harder it is to find what we need and therefore harder to use the networks we’ve fought so hard to build.

Big networks aren’t intimate and discourage reciprocity. Social networks have designed features that encourage ‘broadcasting’, ‘scrolling’ and ‘feeds’ with many people, which in fact, serve to weaken and dilute our connections, rather than strengthen them. Some of the more conscientious networkers actively avoid posting requests of their followers because they don’t want to be seen to be too needy, or to save their ‘social capital’ for their most important requirements.

What if, in fact, you only EVER needed to ask a small number of connections in order to use your wider network more effectively. No more ‘broadcasting’ or ‘statuses’.

“Networking is overrated. Become first and foremost a person of value and the network will be available whenever you need it“ – Naval Ravikant

As Reid Hoffman (LinkedIn’s founder) stated in his book ‘The Startup of You’ “life is a team sport and that anything great in your life will only happen with and through other people”. If only LinkedIn’s product recognised that knowing someone is about intimacy and familiarity. A connection should be an ongoing relationship, rather than a single act or click. Your network should be the place you go get help from and to help the people you know and trust (ironically LinkedIn’s original motto). Social networks should actively discourage you from adding people unless they know them well. I’ve yet to find a platform today that truly understands what the word ‘connection’ or ‘friend’ really means and bolsters that important relationship, rather than undermines it with noise.

Whilst few people realise it, networks are symbiotic – the more you actively benefit yours and invest in it, the more it benefits you. I wonder if it’s time for a more network that takes a more enlightened view of how and why we we network and return to focus on quality, not quantity?

This is exactly what we are passionate about at Wholi– discovering the true value potential of your close network as well as how to unlock it.

Tom sings his rendition of ‘Brown Sugar’ at a networking event

People as Attributes (or how Uber got it right)

In Part II of our series on people search today, online identity and privacy (read Part I ‘Searching for the Self’ Here) we examine how Uber disrupted the taxi industry by recognising that many industries that have traditionally been ‘searches for people’ are actually searches for a very limited set of specific attributes. 

Let’s start with a thought experiment. Suppose you were building an app to find tennis partners, how would you do it? The simplest way would probably be to have people input their location, availability and estimated ability on a score of 1-10. You would probably also want the app to verify that this was a real person, so you might insist on a social log-in but basically what you are interested in is the above three characteristics.

The app would then use a simple interface to make matching with other potential tennis partners extremely easy and would, in an ideal world, make it possible to book a court/set a time without ever having to leave the app. Hey presto, you have a tennis partner.

Essentially what has happened here is that person you are being matched with is being reduced to three key attributes: Ability at tennis, location, availability. Who they are beyond that is unimportant, for the most efficient service to enable the largest number of competitive tennis matches – this is all that matters.

Much of the way that people search is carried out in the 21st century is through this kind of ‘attribute search’. Uber are the most successful example of this. Despite their initial tag line of ‘everyone’s private driver’, Uber have actually done something rather different. Uber have successfully commodified the attributes of their drivers to the point where the personality of the driver has almost completely been erased, as exemplified by the relatively recent feature allowing the passenger to play their own music by connecting their Spotify. The driver is there to provide a journey; he or she is not there to be a person.

A CBS Insights Report

Unlike with our tennis player example, the ‘ability at tennis’ score is the product of a service-side verification by Uber. We do not really care that our driver is a 10 not a 7, what matters is that he/she is above whatever the threshold is that defines a ‘safe driver’. Our tennis player app is essentially ‘Uber for tennis players’, a tagline (Uber for X) that you increasingly see clogging up the pages of techcrunch and on the slides at demo days.

The Uber model of identifying attributes and commodifying them as efficiently as possible (by which I mean reducing the individual who possesses them to that limited set of attributes) is one that has been revolutionary for 21st century capitalism. Many industries that used to require relationships with an individual have no intrinsic reason for doing so, other than a relationship was required in order to get that service. For instance getting a plumber to fix a sink does not require any relationship with the plumber, provided you know their ‘ability at plumbing’ attribute is above the threshold for competency. A more efficient system would be an Uber for plumbers, meaning that you don’t have to wait for ‘your’ regular plumber to be available and that demand is more effectively spread around the ‘competent plumber’ work force. There are other useful market forces at work here that help make the market more reliable – i.e. more full of cherries than lemons. Clearly an ‘Uber for Plumbers’ leads to a desirable outcome for both consumers and competent plumbers, but it does mean that people no longer have a relationship with the person who comes to fix their sink (whether or not this is a desirable outcome is of course up to you).

However there are many industries that cannot be ‘Uberfied’. Hiring a full time employee is someone you see everyday, you can’t just bring in a rotating series of temporary workers summoned at a moment’s notice. There are skills that have to be learned, personal relationships that have to be established. Above all there is no ‘minimum competency threshold’ that applies for all cases. What makes someone a good employee in one team may make them a terrible one in another, people are different and work together differently.

Let us return to the tennis player app though experiment. Yes it’s efficient, but is it the most desirable system? Does it produce the maximum utility for its users? People don’t play tennis in silence, they arrive at the court a bit early and hang around waiting for their time slot, they take breaks between sets – standing in awkward silence during these moments would be far from desirable. Suddenly, wouldn’t the app be improved if you could see the interests of potential partners? Wouldn’t the tennis game be more enjoyable if you had a shared topic to talk about between sets?

This guy is probably too good to be on the app

Taking it further – what if the person was from your industry? Someone you might potentially bump into in meetings, or might be good for giving you user feedback down the road? Perhaps someone who knew similar people to you and so you could interact with both on the level of tennis but also turn it into something with potential business benefits, or whom you could interact with on a social level by gossiping about mutual acquaintances, or on the intellectual level by talking about your shared love of art or literature.

Someone who lives in the same location as you, is free at the same time and has a similar tennis ability, while also sharing at least one of the above attributes would be the ‘optimal’ tennis partner. At Wholi, this is the kind of relationship we want to help create in the long-term – by expanding the attributes to describe the person behind them rather than severely limiting the attributes to create ‘an Uber for X’. We want to create ‘people search’ not simply ‘attribute search’.

Life is short, why waste time playing tennis with people with whom you have nothing in common. Uber revolutionised how we think about hailing a taxi, and the lesson we can learn from this is that they were able to revolutionise people search taking the ‘personality’ out. With richer contextual information it will, long term, be possible to not only make people search incredibly efficient, but actually able to foster more meaningful connections than those that currently exist.

Recruiting for permanent roles is clearly one industry that cannot be ‘uberfied’, simply because (despite the best efforts of Meyers-Briggs devotees) what creates a good employee is not simply something where being above an ‘attribute threshold’ is what matters. Any time personality play a big role in a relationship, that relationship is ‘uberification-proof’. Hiring, finding an investor, a mentor, new friends, people to date, people to travel with, people to play sports etc. with are all examples of huge industries with a number of existing solutions – industries which cannot be fixed by tapping a button and immediately having someone who is ‘good enough’ sent to you. We believe that all of these industries can be improved through richer contextual people search, where the attributes of someone’s personality play a determining role in putting great people in the room together. Thinking about people as attributes has allowed Uber to shape the way we think about the service industry, but recognising its limitations is vital to building a world where the best people are more easily able to find and contact each other.

Searching for the Self

People search is a fascinating area. Almost everyone has an opinion about it, even if they haven’t exactly realised that’s what they have an opinion on. In the following series of articles, we’ll be examining online identity, people search today and privacy (aka the creepiness factor). What follows is Part I: Searching for the Self

You are not who you think you are. You’re perhaps sitting reading this on your phone, with one hand propping up your head, imagining that you’re a complete person. Digitally, you’re wrong. What you actually are is a collection of different fragments, scattered across the wide expanse of the Internet, which are linked to you, define you and represent you. You don’t know where a lot of them are, you don’t know what combination of them people are seeing and you don’t know how that makes them think of you. At Wholi, we’re trying to change that.

Our aim is to build a search tool that enables the right people to find each other by aggregating public information in one place, and giving users the ability to curate and manage this collated identity. This will allow people to not only see what the world sees when they search for you, but give you the power to reshape it. We want to do this without losing the flexibility that the Internet has given us to define who we are differently in different places. Because of this, what it means to have identity online is our central concern as we build Wholi into the pre-eminent platform for finding people.

If you’re looking to find someone, where is the first place you look? The answer to this question has changed dramatically in recent times. Searching for someone is now synonymous with searching for his or her information. Identity is now comprised of information, aggregated from all sorts of different locations. Fragments of our selves exist all over the Internet, yet the aggregation of those fragments is unlikely to be equivalent to any singular ‘self’ that you would recognise, like trying to build Frankenstein’s monster from an eclectic mix of body parts. Finding the right fragment-answer for your specific question is the fundamental challenge of building a tool to enable people to find each other most effectively.

The fragmented self

People search already has a significant impact on our lives, but is complicated by the fact that we are not the same person in every situation. We are frequently impacted and shaped by powers beyond our control, powers derived from the contexts in which we find ourselves. Put simply, you act differently in different situations – to the extent that we can think of these situations as producing multiple version of yourself (think how you act in a library vs. a night-club, for example). The way we act is often derived from the external forces that act upon us – yet this is something which people are very bad at recognising. Social psychology calls this the ‘fundamental attribution error’, which means that people have a tendency to place undue weighting on their internal disposition as opposed to external factors. By way of example: if someone crashes their bike people are more likely to attribute this to their being a risky cyclist, rather than the fact that the road is slick with rain.

Yet identity is significantly influenced by outside forces. One of the reasons, perhaps, why sociology is less well understood to be an important discipline is that it appears to undermine our own agency – we think we act entirely through self-determination as this is how it appears to us, and don’t like the idea that we are suspended in strands of culture, power and influence which curtail and direct our behaviour on a daily basis (if this interests you check out either Michel Foucault or Pierre Bourdieu). We dislike the idea that there is not an essential ‘I’.

Every time you search for an aspect of someone’s identity online, you are searching within a given context for a particular aspect of who someone is. When you search on Yelp and find Sarah, the plumber, you are searching for her ability to fix your sink, rather than as a friend, tennis partner, or for her specialised knowledge of how to grow geraniums in the acid soil of West London.

Individuals are represented as different people in different contexts, meaning that the information about people that exists in the contextually different parts of the Internet both reflects and actually constitutes the person. For instance, if Sarah the plumber’s rating goes down on Yelp, she will be perceived to be a worse plumber and might well get less work, which will lower the number of her ratings (in itself an indicator of popularity) and the cycle will continue. The days of saying ‘it’s just the Internet, it’s just words, it doesn’t matter’ are long behind us. The words on the Internet are inescapably tied to the person we are offline, changing the words changes the person.

In many ways, this fragmentation is an extremely good thing, as it allows us to more accurately recognise the way in which contextual forces shape our interactions and our behaviours and to isolate the specific part of an individual that we want to interact with. For instance, when our sink is broken we do not care that Sarah is a good tennis player or expert gardener, all we care about is her ability with a spanner. For this reason distinct platforms exist to find these different forms of Sarah: she is on Yelp as a plumber, as a tennis partner and for her knowledge of flowers.

tricky things

So what should a modern people search tool look like? Clearly we are different people in different contexts, so meshing all the different ways it is possible to interact with someone into one generic platform could easily become a backwards and confusing step. For instance a platform that was functionally a merger of LinkedIn and Tinder would be very confusing, as the way you communicate with someone on a dating app is manifestly different to how you would in a professional context (unless you’re a misogynist who has watched too much Mad Men). For this reason, having distinct search tools to find a prospective partner (Tinder) as opposed to a prospective employee (LinkedIn) is an easy way of marking that distinction and preventing confusion.

However, even if we want to keep the communication channels distinct to protect separate registers of appropriate speech, the attributes valued within one context can overlap with another. When we meet someone on Tinder we might well Google them and pull up their LinkedIn to see whether or not we might be compatible (the reverse, of course, is also true but here is not the space to get into discriminatory hiring practices). Someone’s job, or education, or the fact that they are a great plumber, tennis player or gardener might well play a big role in someone’s choice of a potential partner. Attraction is a nebulous thing (We will go further into how Tinder has revolutionised search in the context of dating in Part III). It might be a minor role, of course, but in finding the right person for you the fact that someone plays tennis could well make him or her more eligible. To use the language of people search: it would make him or her a more relevant ‘search result’.

There is a vast amount of public data on the web. When we try and find people to build relationships (in the non-romantic sense of the world) all sorts of elements of their fragmented self come into play. The modern world increasingly reduces human interactions to transactions (see Part II) but there are still plenty of contexts where having a relationship with the person who is a combination of those fragments is still extremely important (for instance, when you hire someone to do a job they need to be good for the task they are hired for (a specific attribute), but their personality and how they fit with the team is just as important); it is not possible to remove personality from the “equation of good fit” and the effervescence that is created when the right people are in the room together is one of the core reasons why great businesses, enterprises, revolutions and artistic movements succeed.

As this unique ‘good fit’ is so important, using technology to put the right people in the room together is an extremely important and interesting challenge – the one which we are trying to solve here at Wholi. An effective people search tool will be able to reveal people in the specific context of your search, while acknowledging the fact that the person you are looking for has other attributes that might make him or her the right ‘search result’. This is already going on. Every time someone Googles a job applicant or potential date they are pulling in information from all across the web in an inefficient way to build an incomplete picture of that person. A picture which that person has limited control over. A modern people search tool will make finding the right person more efficient, not by removing or reducing the efficient fragmentation of personality that has been enabled by different platforms, but by acknowledging it.


Photo Credit: ‘I’m watching’ By Alejandro Gomez on Flickr

The Happy Entrepreneur

Is a ‘happy entrepreneur’ a misnomer?

Being an entrepreneur is hard. Really hard. Or, in the words of Elon Musk, “Being an entrepreneur is like eating glass and staring into the abyss of death.” If that’s what it’s like when it’s working, given Elon is one of the most successful entrepreneurs alive, what hope do the rest of us have of enjoying it? Ouch.

I’ve spent a lot of my career recommending people become entrepreneurs, but sometimes I hesitate. At times I’ve coveted a 9-5, well-paid, corporate job. Admitting that, I feel a bit like a traitor to my vocation. Like David Attenborough suggesting he’d rather be an endangered species taxidermist. But the more I learn and talk to others, the more I learn that this is normal.

In this article, I want to address some of the things that I wish I’d known, or learned, sooner on the entrepreneurial journey. I believe there are ways to be happy as an entrepreneur, yet very few of us are and it requires even more work and focus to become one. 

Why Entrepreneurship?

Entrepreneurship is, in many ways, amazing. There’s something captivating about it; it’s empowering, creative, exciting and addictive. It’s a powerful, if not revolutionary, force in the modern world; with an intoxicating Schumpeterian ‘Creative Destruction’ occurring at rapid place in the music, media, hotel and taxi industries, to name just a few. As parodied in HBO’s fantastic Silicon Valley, entrepreneurs aim to “make the world a better place,” (and sometimes they even do)!

Despite how hard it is, it’s rare that people go back to a corporate job once they’ve tasted life in a startup. Yet for all of the media glamorisation, it’s often deeply unhealthy, stressful and – particularly in the tech sector – entrepreneurs have an extraordinarily low probability of success.

Probabilities and Hardship

By way of example, Google has 56,000 employees and more resources and freedom than perhaps any other company in terms of innovation. In 15 years it has come up with just one monetisation technique that contributes to ~95% of its revenues. Just one.

At the other end of the spectrum, 80-90% of startup founders that receive venture funding don’t exit with more than their (usually dramatically reduced) salaries. Just 0.1% of pre-funded tech startups ‘succeed’. That’s a terrible compensation for the stress and impact on their lives. The resulting psychological impact can be extreme, as these articles demonstrate:

Founder Depression by Sam Altman

Brad Feld, Depression 

Business Insider, Founder Suicides

The Journey

This photo, of the Wholi team on a retreat in Italy, fairly neatly sums up the journey...
This photo, of the Wholi team on a retreat in Italy, is a fairly good representation of the startup journey…

Given the difficulty and unlikely success, it’s important to try not to base all of one’s happiness on a result. One of our values at Wholi is enjoying ‘the journey’ – meaning that we want to enjoy the process and the day-to-day – regardless of the destination. Our values are aspirational as much as actual, a recognition of the things we want to be rather than necessarily the things we are. When things don’t go well – which they often don’t in a startup, it serves as an important reminder.

Mostly speaking, I have not been good at enjoying the journey, (Wholi’s journey is captured here on our Facebook page). I am beginning, slowly, to listen and act – to stress less and enjoy it more – with help from my team, peers and investors.

I am not transformed. The gulf between my ideal and actual self will always be there, but I am in the process of making some changes and I find writing one of the best ways to process, to understand and to set intention.

What follows is a (non-exhaustive) list of some things I’m working on and things I wish I’d done earlier, in an attempt to help others, or those starting out: 

Find out what you’re good at. Leave the rest.

I’ve only recently started coaching, so I can’t claim any Damascene moments just yet, but I am seeing glimmers. My coach tells me that his role is to find what people are naturally amazing at and help them find ways to focus those talents and leave the rest.

If there was a single piece of advice I could transmit to my teenage self it would, I believe, be this.

The issue is that what we’re good at often comes naturally, therefore we don’t identify it as a skill – we think it’s just ’normal’ – and as a result we don’t harness and enhance these skills into a super power.

One of my skills is empathy. I can often read a room, or a person, and am highly attuned to small cues, feelings, sensations and the emotions around me. Yet for many years – particularly throughout school – that empathy, or sensitivity was a weakness to be covered up, not a skill to be harnessed. I’ve spent far more energy trying to be tough than I have nurturing that skill and turning it into a superpower. Time to listen.

The ‘leave the rest’ bit is vital for entrepreneurs. The role often forces us to do a bit of everything. For me, I believe that has been destructive. Trying to be good at, or forcing the things that aren’t skills, has consumed a huge amount of energy in my life. Entrepreneurs often focusing attention on and believing that we must tackle every challenge. This is a mistake.

A initial closer analysis of my own ‘work’ has uncovered that many of the things that I’m best at, I don’t consider work and therefore I regularly feel guilty that I’m not working enough – even though by some measures I’m working a lot harder than I realise.

Certainly entrepreneurs will have to do things they’re not good at, but I believe that it is only by harnessing our natural strengths, focusing on them and recognising them – sometimes to the detriment of other ‘important’ things, or harnessing other people’s strengths to cover these – that we can truly be successful and happy; both in entrepreneurship and in life.  

Energy & Putting your own oxygen mask on first

Follow the advice about finding what you’re good at will transform (at least in my limited experience) one’s energy. If you harness a natural momentum, it’s easier to make progress.

If there was one measurement that would correlate with my being a happy entrepreneur (and therefore more likely to be successful), I believe it’s ‘energy’. Meaning how you feel on an energetic level — read this excellent HBR article for a better understand of what this means.

A friend (who’s also a coach) sent me this, claiming it’s one of the most important articles she has read when it comes to helping entrepreneurs. I agree. ‘Put your own oxygen mask on first’.

Entrepreneurs should be incredibly sensitive to their energy and foster it wherever possible. If you need to justify free weekends and evenings, just look at the HBR article in some more detail.

Founder Confidence

I’ve read a collection of articles recently about founder confidence and how often the brazen pitches and networking displays mask deeper, destructive insecurities that plague many founders.

Again, these tie into the previous two sections. If we find what we’re good at and leave rest, then focus on maximising our energy, we build confidence. Confidence is key. Entrepreneurs need to continually make decisions and hope they’re right. Often they won’t be. Yet we must have confidence. Study leading entrepreneurs – Elon Musk (despite how hard he claims it is), Steve Jobs and others and you’ll hear of a boundless confidence. I believe that confidence can be cultivated.

Get Support

Get help. Seriously.

Entrepreneurship is a lonely game, compounded by the need to present a positive, upbeat face to customers and your stakeholders. This exacerbates a failure to seek and ask for support.

Entrepreneurs need, desperately at times, to set up support mechanisms to help them. In my case a quarterly meeting with fellow CEOs where we ‘lift the kimono’ and describe what’s actually happening, provides some solace. Coaching, friends, team members, fellow entrepreneurs, networks, articles and other sources have too, but they need to be cultivated. Get over the issue of worrying that people will judge you because you have problems and ask for help. Lots.

I am still not very good at this, but trying to get better. Mark Suster wrote a great article about getting your mojo back here.

Finding Balance

Entrepreneurship is hard. So we put up with lots of hard things that don’t need to be so. A fellow entrepreneur I know gets up at the crack of dawn to catch early flights in order to ‘seize the day’. I believe it’s a huge drain on his energy and negatively affects his work. Another pulls an all-nighter once a fortnight, again, I believe, creating more of a deficit than a gain. As entrepreneurs, we should be looking for ways to make life easier, not harder.

I don’t schedule in early meetings, or fly late at night, or on weekends – even with an office in Romania. I spent a year carrying things to and from that office, before deciding to invest in two pairs of running shoes, two yoga mats, two sets of toiletries and so on. A small change, but my travel burden is a little easier. I try to ‘work like it’s the weekend. I worked from home for almost 2 years, before I realised it was much more costly to one’s emotional health than the expense of renting an office. My own battle with balance was the topic of my TEDx.

At Wholi, we have some role models who have found a semblance of balance. We love Richard Semler of Semco – his TED is here. Yvon Chouinard. 37 Signals, and Buffer. Whilst we at Wholi are in pre-product market fit phase, these companies have managed to grow into significant businesses whilst maintaining some balance and doing things differently. That’s truly inspirational.

If your life depended on it

There is a lot here, so much so that many of the topics could be an article – a book even – in their own right. Depression, stress, energy and so many solutions from meditation, sleep, diet exercise, therapy, coaching, holidays, avoiding things you’re not good at, mindfulness.

To sum up, if you were going on a polar expedition, you would be fastidious about your energy, your equipment and your health. While being an entrepreneur involves a lower risk of frostbite, it’s often a longer, harder journey.

If you’re an entrepreneur, treat getting this right as if your life depended on it. It does.

Sometimes we even go to cafes named after our values, just to remind us...
Sometimes we even go to cafes named after our values, just to remind us…

Fun Raising

wholi founder Raz in whotopia...
Wholi co-founder Raz – one of our secret weapons when fundraising to build ‘whotopia’

Forget what you know about fundraising. It’s changing. There’s more money available from more sources, and more people chasing that money. So unless your numbers are so captivating you can walk into Sequoia and blow their socks off, it’s you that’s going to have to be working yours off…

We’ve spoken to hundreds of startups looking for investors. In this article, I want to share a few of the best tips we’ve discovered or heard, as well as revealing our learnings from wholi’s most recent round. Plus there’s a very special offer at the end of this post for anyone currently fundraising. 

First up be warned, there’s no magic bullet. Fundraising is hard. I’m purposefully not writing a fundraising article entitled ‘10 easy ways to…’ because I’ve yet to come across a way that’s easy. Perhaps many founders wouldn’t start the climb if they realised what’s involved and seek alternatives. There’s nothing sadder than a company running out of money and desperately seeking investment if they could have spent or even saved the time earning revenue instead. Don’t do it unless you truly need to and understand what it takes and what it takes out of you. 

Somehow, tech has become sexy. The place to be. Most startups that I speak to are targeting higher numbers of investors, meaning more noise in the market. Fundraising is increasingly a ‘numbers game’. Successful companies aren’t necessarily the ones with the best products or metrics, but instead the one who work hardest at their process of finding investors. If you’re prepared to commit to do the work, here’s how you can improve your chances: 

Stand on the Shoulders of Giants

Before I start with the people search component of the fundraise, please read this: – It’s oh so wise, and I won’t repeat much of this advice. Read it 5x (it’s long) and then follow his advice to the letter. When you get stuck, read it again.

A shoulder to cry on

I would add one additional idea – and I cannot recommend it highly enough – which is to find someone who’s done a fundraise before and pay them to keep an eye on you, make introductions and be a shoulder to cry on. See the end of this article for a special offer from us to help one of you, for free. 

We spent $50k over 6 months. It was worth every penny. I’m not suggesting a fundraising ‘consultant’, god no, I’m talking about a founder who’s done this before who’ll double your chances of success and is hired specifically for that task and probably hasn’t done it often before i.e. they’re not making a career out of fundraising.

Process – your safety belt in turbulent times

In two previous blog posts here and here I explain my somewhat exhaustive process for recruiting an amazing team. Seems like a lot of work, right? That’s why Graham says that fundraising is a full time job, because it’s a similarly gruelling process. You need to ‘commit’ to the process. 

Abraham Lincoln said “Give me six hours to chop down a tree and I will spend the first four sharpening the axe”. That is also true of a good fundraise. Many of the tips I describe for people search there apply in a good fundraising process. If you don’t know your boolean modifiers, where to start when X-raying a site, or what the features of the investors you’re looking for are, get sharpening. 

Your process is your safety belt on the fundraising rollercoaster ride. Invest time and if necessary money researching and building this process of finding people and keeping track of who’s who, how to reach them, where to get intro, how to mine contact information, find email addresses and get introductions. 

Introductions are, by far, the best method of getting hold of people but don’t be afraid of cold-emailing people too. Most people don’t bother because it’s not recommended, but you can get a lot more cold emails out than you can intros so as long as you’re not burning bridges, try. If you know how to write a great email and personalise it, you’ll get responses. I met perhaps the #1 investor in the world because of a cold email. It still works. Gratuitous name-dropping often helps – “I’m meeting X and Y, so thought that it might be worth coming to see you too”. Investors will tell you absolutely not to use this technique (because it makes them seem like lemmings), but I’m afraid it works (because they often are).

How it Goes

This is how over 200+ startups we’ve spoken to run their process. I’m sharing this for two reasons, firstly there’s probably a lot of tried and tested wisdom in this simple process… AND if this is how everyone else does it maybe there’s something you can do differently?

  1. Build a target list (almost everyone builds them in spreadsheets – but as the number of people you need to store is in the hundreds we think wholi is a lot easier)
  2. Filter and prioritise the list
  3. Getting in touch and starting the conversation
  4. Building on the conversations, working through your pipeline and getting second, third and subsequent meetings

Also, remember that if you can shave 20% off any of these steps, you’ll save yourself days of time. Optimise. Treat it like you would a marketing test.

Lists and Number Games

Behind almost every great fundraise is a list of investors. Not a measly 20 people you might want to contact but literally hundreds upon hundreds of names carefully curated and crafted.

On arrival at 500 Startups and, I’m told most every accelerator, one of the first things they’ll tell you is compulsory is to build a detailed list of every investor that might be applicable. There are ~30k investors in our ‘who list’ – your aim is to build a list of 200-400 people who *might* invest. Over the course of your fundraise you’ll probably contact every one of them 3x via different methods. One of the reasons why wholi is focused around a list is that it forms the backbone of every good search and is many times more powerful than a spreadsheet.

As well as us, there’s CrunchBase, LinkedIn, AngelList, Owler, Conspire and many more sites that should be able to help you identify the right people and work out how to get introductions. I’ve mentioned it’s a numbers game. It’s true on the other side of the fence too – here’s a picture (below) sent to me by one of my investors. In 60 working days days, they had 157 first meetings, close to 3 a day and probably another 60 meetings for follow on. If they’re playing the numbers game SO SHOULD YOU.

Screen Shot 2016-07-15 at 18.12.48

The opening number is red is companies MET. Think how many people were identified and then contacted before that. There would be two numbers to the left which are probably in the region of 1000 and 400, and that’s on the investor side, where most people will take a call. Told you it was a lot of work. One more thing to add and this is very important – your aim is to pique enough interest to move to the next stage of the process. You are NOT trying to get them to invest at that meeting, or with the first pitch deck. Remember the two rules of business:

  1. Don’t tell people everything you know

Filters and Priority

There’s a reason why the wholi investor list has certain filters. For example, if someone hasn’t made an investment recently, you probably aren’t going to get anything out of them either. Prioritise your time. Make sure your location, round size and category is applicable to the person you’re contacting. Get intros from or find investors through similar companies that have already fundraised. The reason why we include as many social profiles as we can is that blog topics, tweets, Facebook photos all give you indication of who you’re after and how to grab their attention.

Don’t be British

When finding and reaching out to people, the best piece of advice I can give is don’t be British about it. I had my Britishness beaten out of me when apologetically pitching wholi (or 3Sourcing as it was then) to the Californian startup crowd.

Hustle. Be bold. Our lead investor blew me off 2 or 3 times because he’d just had dental braces put on and couldn’t really talk on the phone. I simply saw that as a challenge. We got onto 500 Startups because I randomly tweeted Dave McClure and said we were interviewing at YC. I’d tried reaching out to him and other partners a dozen times before to no effect. As far as I’m concerned no reply means they haven’t seen your message. A vague no means try again!

I called one of the most famous angel investors in the UK on her private mobile in the evening and caught her cleaning her fish-tank with her daughter and that resulted in a meeting. You’ll have to try different methodologies and tweaks. There are hundreds of times I’ve mailed, tweeted, called people to try to get a foot in the door. Sorry investors, if you’re going to have one of the most desirable jobs in tech and take less risk, there’s got to be some downsides 🙂

Try messaging people where they don’t normally get messaged. Send snail mail. Message them on Facebook. One tip a Chairman of a FTSE100 company gave me was that if you want to get someone on the phone call the most senior person at that company (not the person you’re trying to reach). You’ll get through to their secretary/gatekeeper, then apologise and say you want to be put through to the person you originally wanted. Often, because your call has come from the secretary of the more senior person, the next secretary will presume you’re important and put you through. Try stuff and see what works for you.

Our Fundraise

At wholi, we completed a significant funding round early this year (2016). Whoop say the headlines, #whatthehellwasthat say my wrinkles, sleep patterns and hairline. Behind the scenes, a fundraise is an intensely tough, stressful, uncertain and (I think for most founders) unenjoyable experience. It’s somewhat fetishised by the press – a stamp of approval – but most scarred and battle-weary entrepreneurs will tell you they’d be happy never to do it again.

In our case, I don’t think the stress levels were helped by the fact I also slept in a tent, in the woods in Somerset, UK in rainy October throughout the process (, whilst also trying to write, prepare and give a TEDx ( Although if there’s one thing that will give you perspective, it’s sitting in a boardroom somewhere in moneyland (one investor had pictures depicting a firing squad on their walls, I kid you not) during the day and then cooking pasta pesto over a hob in the rain in the dark, whilst listening to owls the same evening.

Good luck.  


A Special Offer: If you’re about to start, or are currently fundraising, then I (Tom, wholi’s founder – raised over $7m) will be giving one startup two days of my time to help you raise. I’m pretty confident I’ll be able to increase your chances by making introductions, helping with your pitch, your list of potential investors and so on. If you’re interested, please contact andreea at you know the rest dot com and let us know when you’re starting the raise along with your pitch, AngelList or other materials. We’ll be selecting startups on the basis of my ability to help them, coupled with their willingness to do the work 🙂 – looking forward to helping.

Bonus: If there a number of good enquiries, I’ll do my best to try to help pair you up with other entrepreneurs that have raised money before who might also be able to help you. Apologies if we can’t help you all.

The (Somewhat Mental) Recipe for Recruiting An Amazing Team – Part 2

The Wholi Team – Day 1 in the office

See part 1 of this post here –

In the previous post, I talked about ‘the search’ process when it comes to finding new people here at wholi. In this, I’ll look at the next steps – initiating discussions with candidates and using your networks.

Stage Two – Discussions

1) Once you’re at ~process 3) in the previous post, you should also start trying to reach out to the best candidates and begin talking to them. Go slowly at first, you want to learn as you go.

2) We wrote a template email, in Romanian, from my co-founder Raz (who’d won 2x medals in international olympics, got a PhD in AI etc) and then personalised the email in specific places for everyone we wrote to. We were careful to include things that were attractive, and also said that we know ‘you’re probably not looking but it’s always good to make a great connection’. The email is worth spending some time on and, given the investment in time it has taken to find those candidates.

3) We sent small batches of emails, monitoring the response rate and tried to learn what would increase the likelihood of getting a response. We followed on with people who hadn’t responded after a week or so, sometimes finding alternative emails for people if possible. In our case, we received a ~30-50% response rate, perhaps higher later on in the process once word got round. Be careful at this stage – if you’re emailing lots of people who might know one another then you want to make sure they understand that this is part of a process to find the right people. There’s a fine line between spamming and sending emails that are of value to people – in our enthusiasm, we’ve got this wrong before. 

4) When my co-founder got a response, he passed it on to me and I set up a call with the person for 30 minutes.  I also suggested they see our presentation at 500 Startups ( to show them what we were about (and to try to further pique their interest). I suggested a quick call even if the person wasn’t willing to look for a new role or said they’re happy where they are. Most great people aren’t looking for something – this is the beginning of the relationship and often conversations that start at this stage can take years to turn into a successful hire. As I write this, I’m sitting opposite a colleague who initially wasn’t interested. I suggested a call and slowly but surely, when we talked more and more he became more excited about wholi and eventually joined us. 

5) During the conversation, I tried to: a) give a good pitch, tell them about the culture we were trying to create and that we’re only hiring the most amazing people, b) take notes on every conversation so I knew what they’d said and c) make sure to ask them who they think the best developers they’d worked with. c) is vital as the more conversations I had, the more often I heard the same names, which enabled me to know exactly who to target. This list of people regularly mentioned became our ‘dream team’ list. If they were friends with other people I was talking to, I’d also ask if they knew that person – no more than that, and monitor reactions (LinkedIn connections are useful for this). These names, if new, were fed back into the spreadsheet and also recorded and sometimes the ranking adapted if people were regularly recommended. As I mentioned at the beginning of the last article, if you already have or know of amazing people ask them who they would work with if they could hire anyone, this can save you a lot of time.

6) If the person was good and interested, I passed them over to Raz for another, more technical conversation and also tried to follow on with some more juicy pieces about the company, to keep them keen. Even if they weren’t interested, I’d recommend they drop into the office sometime for a chat, just so we can at least put a face to the name (this often sparked interest) and sent them materials/reading etc and tried to keep up with them. By the time you’ve got to this stage, you’ve invested a lot to find these gems, so treat them carefully. We keep emailing people until they’ve dropped by to visit us – once they see/get a feel for the office/team, it often changes people’s minds.

7) If after review with Raz there was mutual interest, I would have another longer talk and we’d also schedule in some time to work together, preferably for a half-day or more. There’s nothing quite like spending time working on actual problems with someone to know what they’re really like. Even after following the process above, about 50% of all people who have come for a working day are not hired. On the day itself we’d once again we’d ask for recommendations. Deciding what tests to do (and should be set by your expert in that field) is up to you, but point to the key features you want. Its worth investing time in this process. We also give detailed feedback for every candidate who comes to a working day – if they’ve made the effort to spend a half day with us, we want to be clear what didn’t work constructively so that the candidate gets something out of the process. That’s very important to us – we want the people not selected to leave feeling sad they didn’t get the role, but that the opportunity and team at wholi made the process the best it could be. Make sure you continue to take notes, so that someone else can understand where you are in the process, and what to look for in a candidate. Especially if there are a number of people hiring, but also be careful not to bias decision-making with opinions. I often ask very different questions from Raz (I’m a gut feeling, emotional, EQ person, whereas Raz is a logical, IQ, quantitative brain). Often the two of us will spot different patterns, which can be valuable. 

8) If you decide you do want to hire someone, one of the most important parts of the process is checking references. Use your notes to ask difficult questions of the referees about specific things that are of concern. Also check references with anyone you know who the candidate has not volunteered, to see if there’s a bias (although be careful, given candidates might not want people to know they’re leaving). Get as many references as you can (I went for 5/6 for most people). In addition to checking references, referees can shortcut your ability to learn how best to work with someone. It can take months to ‘discover’ what motivates someone and how to work with them. By asking referees how they would manage that person, or what to look out for, you learn a lot about speeding your process of building an effective working relationship.

9) If people are not interested for whatever reason but are on your ‘dream team’ list, keep in touch with them rolling forward and update them as to the progress of the business, as you would investors. We have a list of 25 or so people we stay in touch with every few months. I add them on Facebook, LinkedIn, Twitter etc. I post cheeky messages on our Facebook pages with them tagged in ‘future employees’ section (see below). Basically I stalk them and send a continual stream of abuse until they join us 😉

Tagging people who we want to join us...

After a while, if you’ve built the right team, these folks start to let you know when they’re free/interested and what’s happening in the market.

10) I ask my team to keep in touch with these folks (all the best people know each other) We’ve built a Facebook page in which we record some of our company history (and some photos in Wholistory – forgive me) and some of the team trips we’ve been on. We’ve been lucky enough as a company to go on trips to Malta, Sicily, Skiing and to Kenya – these have been amazing fun, excellent bonding experiences and helped us to take time out of the office to set values, assess what’s working and what’s not, etc. This year we’re off to the Romanian countryside, Montenegro and are planning our return to Kenya next Spring. 

Stage Three – Networks 

1) In addition to the above techniques you want to find people who can spot great talent for you. Email and try to develop relationships with key players like university professors, other entrepreneurs and people who will see the kind of candidates you’re after. Try to keep in touch with them every so often.

2) Now that we have an amazing team, our focus has shifted to using the team members to help us with referrals. Again, this is something we’ve built into the wholi product so that we can make finding the right people much easier for us, and we hope you too. We experimented with this and managed to build a list of 100+ people we wanted to hire in the space of about an hour, by asking each of our team to add people from their contacts. 

The process is hard and takes a lot of time… but it’s worth it. I hope this helps.

Good luck, happy hunting. Let me know in the comments if you’ve any further thoughts…