The Myth of Smooth Success

When most people see entrepreneurs succeeding, they often think or remark something along the lines of, “Wow, that guy [or girl] really has it figured out. They just keep rising.” 

While it may be true that the entrepreneur is doing a great job and operating at an advanced mental level, the mistake often made is that their rise has been smooth, either professionally or personally. Everybody knows that founders work incredibly hard, but so many are fooled that hard work and clever decision on their own are enough to succeed, over and over again.

In my limited experience, I’ve found that there’s a little more to this game than just smarts and laboriousness. After all, people need that to succeed at just about anything in life. In startup entrepreneurship however, there are a lot more unknown and difficult variables to contend with. These could include issues like market timing, tricky investor relations, co-founder politics, or managing a difficult cash runway. It may sound straightforward, but dealing with any of the above when pushed to extremes can feel like a life threatening situation, and raise a person’s stress levels to dizzying heights.

As such, “success” tends to show up when the founder has learned to continuously weather these variables and survive- while working hard and cleverly of course- until good things happen. That’s what people often refer to as “getting lucky”. Even founders, when speaking of their successes will make statements like, “I got lucky there”, or “That deal came out of nowhere”. Was it luck? Well, yes, to an extent. But in my view, if you stay in the game long enough you’re bound to get lucky at some point. That’s really what it’s all about- being tenacious enough to survive the difficult scenarios; again and again and again.

On the surface and to the outside world though, everything can seem hunky dory. Founders tend to hide their struggles, internalizing them and not wearing their hardships on their sleeves. When viewed in perspective, victories are unimaginably hard won at times, yet this is unseen by most. And therein lies the myth of smooth success.

The Happily Unexpected Consequences of Engineering School

After several months off, I’m back. This article was originally written for the inaugural edition of my Alma Mater’s engineering student magazine. Enjoy.

The Happily Unexpected Consequences of Engineering School 

I have always held a deep, energetic passion for technology. When I went to study a double major engineering degree at UCT [University of Cape Town], I was excited. What would I learn? Who would I get to work with? How will I use these skills in my career one day? These are common questions for any young student. In my case, after leaving university I quickly crossed over into a path of entrepreneurship, where I would I get a crash course in sales, marketing, fundraising, HR and several other areas that I was never taught much about in university. After enough people asked (and continue to ask) me, “Do you regret what you studied?” I pondered this carefully and decided that my answer was a resounding “No”. I have realized that while giving me explicit skills in a couple of technical areas, my experience studying engineering also equipped me with a number of implicit skills that I didn’t even know I had until long after I graduated. It was as though I was building a hidden toolbox of assets over those four years, and in the years since, I have seen that hidden toolbox continue to help me along. You might be wondering what I mean exactly. In this letter I have shared just a few stories that may illustrate my point.

Thinking back to my engineering classes at university, I can recall various courses where the final deliverable had to be a working demo or functional prototype of some sort. I remember building an alarm prototype for Embedded Systems, writing a predictive text program for Computer Science, and even whipping components together on a breadboard to do interesting things with 555 timers in Introduction to Electrical Engineering. The specific assignment isn’t what mattered- what mattered is that they forced us to build stuff and make it work. 

As we all now know, there is a marked difference between theory and practice. Sometimes, things don’t always work out the way the manual stated they would, and we need to do a little trial and error. At other times, we need to create a hack or workaround and pray that it holds up under testing until we have time to develop a more fundamental solution. Things don’t always proceed as planned or on schedule, but deadlines are deadlines. And it has to work, or you could fail. This sounds a lot like a real world product development cycle. In startups, tiny teams are forced to create working products in a short space of time, and it’s hardly ever as clean and straightforward as one reads about in business literature. Fortunately, all of those thoughtful planning sessions and hair pulling fault-finding missions during practical assignments offer a solid foundation for us. Engineering grads are rarely frightened by the challenge of creating something new.

In my first year of studies, my classmates and I quickly became swamped with work. Tests, projects, assignments, and the dreadful tutorials piled up. Tutorials were particularly hated, because we had to submit them or risk being disqualified from the course, but their marks didn’t count toward the course grade. At that time, I was living in a university residence, and a clever group of around eight to ten disgruntled like-minded students decided that something had to give. (I cannot confirm if I was one of this group because the story to follow is a little incriminating). Battered by mounting work volumes and not enough time to get everything done well and still enjoy university life, these students developed a novel solution to overcoming tut submissions. Every week, the group nominated an individual who’s job it was to do the tutorial for a particular subject. The night before the morning submission, the group would band together in a res room, as though a clandestine political party meeting were taking place. The person who did the tut would then have to rapidly take the group through the exercise, explaining how he reached his answers and the methods used, and members would have a chance to pose any questions. Once all were satisfied, the original pages of the tutorial solution would be distributed among the different members, who would then creatively copy (e.g. swap variable names etc.) the entire document in rapid assembly line fashion. Seeing the group effectively distribute different pages among each other and cross check each other’s work in a lightening total time of under an hour was a remarkable sight. In the morning, a postman from the group was nominated to submit everyone’s tuts while the others attended their lectures or decided to sleep in. 

Now, I must admit that this was probably (definitely) breaking the university’s rules. And while rule breaking isn’t something that I expressly recommend, it’s something that entrepreneurs often need to do. (Besides, it’s easier to beg for forgiveness than ask for permission anyway, but I digress). While that group of students were possibly “harming their education” by not doing all of their homework solo, they were actually learning hugely valuable lessons in adaptable team work, managing overload, and operating in the margins where those who follow all of the rules wouldn’t care to tread. People strong in these traits are golden to startups. I’m not surprised that many of the people from that group in first year went on to pursue highly entrepreneurial careers.

My next story happened much more recently, around two weeks ago. I was in a casual meeting at a coffee shop with a successful Internet entrepreneur and über-geek, and we were discussing a little business. All of a sudden towards the end of the conversation, the following exchange took place.

"So, I assume that as a business guy, you haven’t ever written a line of code in your life" he said.

"No. Actually I have been a techie since I was a kid; I was a programmer for several years and studied Electrical and Computer Engineering at university" I replied.

"Oh, that’s cool. I was just checking. So if I asked about using a CDN to speed up load times you’d know what I was talking about."

"Yes, we could have a nice debate about the merits of AWS plus CloudFront versus an optimized local box to increase app speed…"

Recognition flashed across his face, a wry smile developed in the corner of his mouth, and we continued to wrap up the business at hand. This type of conversation has happened over and over again in my career as a technology entrepreneur. Even though I don’t work as an engineer anymore, I interact with engineers and technically minded people all the time. And the simple but unfortunate fact of the matter is that if you haven’t earned your chops in a technical faculty before and are unable to stand toe to toe in a technical discussion, they simply won’t extend the same level of camaraderie and mutual respect toward you as they would to one of their own. In my experience, business is mostly a practical skill that can be picked up on the go, while engineering requires deep understanding and conceptual frameworks that are less easy to learn “on the job”. So even though I’m not an engineer anymore and I have crossed over to the business side of the outfit, I am still lucky to be considered as an insider and team player by the technical folks, and that matters massively. To best work with or lead people, it’s essential to understand them. 

Casting my mind back to graduation day all those years ago, I distinctly remember feeling elated- but this was an equal mix between a sense of achievement, and a genuine sense of survival. I’m sure you know what I mean. When looking at that result after a difficult test or exam, sometimes the first thought that comes to mind is not “Look at my incredible mark!” but rather “Wow, I didn’t fail!” Studying engineering is hard. But then again, business is no picnic either, and it’s good to be tough. The outcomes are worth it. And as I am continuing to learn in a career of entrepreneurship, engineering students tend to develop some unexpected but highly useful tools that pay dividends for a long time to come.

5 Great Autobiographies to Read

As you probably know by now, I love reading. Lately, I have been enjoying autobiographies of various flavours. Here are 5 great recommendations. Every one of these books taught me something and made me think in profound ways- surely the hallmark of a successful read.

1. Open - Andre Agassi


This book surprised me by Agassi’s constant revelation of “I hate tennis”. It’s a deeply personal autobiography that really helped me understand his character, his personal struggles and the good and bad of being a world class athlete picked from a young age. I’m a huge tennis fan and grew up watching him play, so his detailed retelling of important matches was probably much more digestible for me than for the casual reader. But the gold in this book lies in realizing how even the elite among us are only human, how even highly successful journeys can end up being lonely, and why having a great partner is so important.

2. Total Recall - Arnold Schwarzenegger


I am self confessed Arnold fanboy. After all, I started bodybuilding at a young age and he is a hero among bodybuilders. And I have huge respect for his success in entertainment, business, and politics. Arnold’s recent memoir has not garnered the best critical reviews, but I don’t care. I loved reading this book. Arnold shares surprising facts about his humble youth in post World War II Austria, and works hard to constantly remind the reader of how it was his relentless focus, drive and ambition that propelled him from achievement to achievement. As an avid gym-goer, I appreciated how many pages he spent describing his journey in bodybuilding and deep interest in health and fitness. There were a lot of excellent business lessons here too, one of the most memorable being not to over think things (or you might quit before your start), but rather just take the leap and get stuck in when you really want to do something.

3. Surely You’re Joking, Mr Feynman! - Richard P. Feynman


Richard P. Feynman had to have been one of the most curious characters of the 20th century. He was a Nobel prize winning physicist, safecracker, amateur artist, professional samba band musician, renowned Caltech professor and quite a Lothario as well. There were a couple of unique things in this book that totally floored me. Feynman had a deep interest in learning things with a desire to fully understand them, working from first principles or inventing his own, and doing work that was meaningful and personally rewarding. He also had plenty of side pursuits and wasn’t afraid to try new things (usually with remarkable success). This strange autobiography is filled with interesting stories and opinions from one of the most fun scientific geniuses I can imagine.

4. Kitchen Confidential - Anthony Bourdain


A close friend of mine recently adopted a career path as a high end chef, complete with studying at a prestigious school and working at fine restaurants. I was captivated by his stories of the brutal, abusive yet addictive professional kitchen culture. Bordain’s memoir really is a tell-all on the kitchen industry, and it’s brilliant. He shares plenty of tips and insights related to food, but this book is mostly about people, the relationships that make the restaurant industry work, and just how different that world is to that of regular office workers. He’s also an exceptional (if rather vulgar!) writer, and this book had me spellbound from start to finish. 

5. The First Billion is the Hardest - T. Boone Pickens


Boone Pickens is a helluva interesting guy. At age 27, he started a drilling company that turned into a small oil empire, then changed the corporate takeover landscape in America, and more recently, focused on trading in energy derivatives and equities, with great success. This book chronicles the most recent chapter in his life. What I found astounding is how, in his late sixties, he got kicked out of his own company, got divorced, faced depression and generally hit rock bottom, to turn it all around in a new company and become a billionaire within 10 years. The energy, youthfulness and mental vigour that he gives off in his eighties are truly remarkable. What I enjoyed most about this read though is Boone’s wry wit and salty humour that comes through in his excellent storytelling.

The Pro’s and Con’s of Frequent Flying

I’m taking a quick break from my usual business themed posts to discuss something that is close to my heart: frequent flying.

Due to my hands-on approach to sales in our company, I have to fly a lot to meet customers or join partner tours all over the USA, as well as internationally. The fact that our company has a head office in Cape Town, South Africa, makes things even more interesting. As a result, I end up flying a lot.

I worked out that in a typical month, I could easily spend 100 hours on planes and in airports. That’s a lot of mileage, and a lot of waiting around. I try not to even think about the dozens and dozens of nights spent in hotels, away from home.

Eventually, you learn to take it all in your stride and live with it, but I still can’t understand why people think the “jet setter” lifestyle is glamourous. It’s not as though business travelers are jetting off to Ibiza or Macau to party every two weeks.

There are some perks though. Here’s a summary of the pro’s and con’s of frequent travel as I see it.


1. Waking up before the crack of dawn to catch a 6:30am flight. This happens more often than you would think. Particularly in the USA, where you are going to be routed through a major hub like Chicago, where you will wait for 2 hours before getting your connecting flight.

2. Security lines. Usually, this involves rapidly taking off half your clothes and ripping apart your carry-on bag, while often stuck behind impossibly slow vacation travelers, or worse- families.

3. Flight delays. A constant irritant in America and Europe’s crowded skies. Especially when you are delayed for hours while sitting on the tarmac after boarding a 6am flight, which is often the case at New York’s La Guardia airport.

4. Wasting time in between things. There is a lot of “filler time” that needs to be spent while traveling. Checking in, passing security, moving between gates, checking on flight statuses, waiting around while delayed, etc. This can be mildly improved by answering email or reading a little, but it’s still pretty much unproductive.

5. Screaming babies on planes. I don’t really need to explain this one.

6. Jumping time zones. You eventually learn to deal with jet lag effectively, but it can scramble your body clock somewhat, causing sleepiness during an important meeting, or ravenous hunger in the middle of the night, which isn’t exactly ideal.

With the con’s now out of the way, let’s move on to the better stuff.


1. Priority access. With good airline status, you get faster check-in, security line skipping, lounge access and priority boarding. For the frequent traveler, these things are absolutely essential, and make a world of difference. I’m not sure if this is just making the best out of a bad situation, but I know that I truly appreciate it when I have it and painfully miss it when flying on the wrong airline.

2. Time to think. Aside from the waiting around in airports, the actual time spent on a plane can often be a peaceful time to read or think. Not surprisingly, I get most of my blogging done on flights.

3. Hotels (if you like hotels). There is a definite point when checking out new hotels produces diminishing returns (no matter how swanky), but occasionally (and especially when my schedule isn’t jam packed), they can be pretty cool.

4. Visiting new cities. Much like the previous point, this really improves when my schedule isn’t insane, but either way, there is the chance to grab a business dinner or drive through town on the way to a meeting. I never get to see the sights on business trips, but at least I can say that I’ve visited a lot of places, sampled the food, and checked them out a little.

5. The camaraderie among regular travelers. Whether they are new acquaintances or old buddies from “the road”, frequent travelers tend to get each other, regardless of age. We can swap stories (good and bad) for hours. The quality of this experience is amplified to great effect when salespeople get together.

That’s it for now. What are your likes and pet peeves about frequent flying?

A Simple Way to Set Effective, Motivating Goals


The new year has begun, and this is always a period of time when I do a lot of thinking about the 12 months to come and what I hope to achieve during that time. The new year is the perfect time to reboot our thinking and focus on a concrete set of goals. Everybody has hopes and dreams, but setting goals forces one to add deadlines, quantities and accountability to those dreams.

In this post, I will share my method for goal setting, refined and simplified after years of experimentation. It isn’t perfect, but it works for me. Let’s get started.

Step 1: Generation

I begin by generally thinking about what I hope to achieve in the year, and let my mind run wild. I don’t want to restrain my thought process into thinking of only “realistic” or “important” things, as this hampers one’s creative ability. Goals should be deeply emotional, as emotion leads to drive and motivation. I write down the first thoughts that come to my head, in no particular order. These aren’t necessarily remarkable or fantastical, but rather just things that I know I want to accomplish in the year ahead. Here are a few typical examples:

  • Grow company revenue to X
  • Close X,Y key deals/partnerships
  • Become a better connector
  • Go on holiday to an island for a week
  • Get leaner and healthier
  • Save/invest X amount of cash
  • …etc

Even seemingly strange, less important goals that come from an emotional place should be captured at this stage, for example:

  • Learn to dance salsa
  • Learn a foreign language
  • Try Yoga
  • Read up on a particular topic of interest
  • Cook a great dinner for my family/friends

Once completed, I usually end up with a list of 15 or so items that get me really jazzed up when I review them. I know that a goal is a good one when I can read it, close my eyes and the thought of achieving it makes me feel genuinely happy and excited. If a goal doesn’t begin from that point of inner hope and belief, it would probably be very hard to stick to and follow over an entire year (and why would you be going after it anyway?)

Step 2: Categorization

In the next step, I try to find any blank spots in my plan, so I take a top down view of my important life areas and write them down as categories. These are:

  • Career
  • Health & Body 
  • Mind/mental stimulation
  • Personal Finance
  • Social/relational
  • Recreation/fun

I then place each item from my original list under the appropriate category. If any category is left blank, I take the time to generate a goal to fall under it, and make sure it passes the emotional relevance test. 

Step 3: Quantification

This is the part where the wording and structure of each goal is analyized. It is imperative that every goal starts with a verb (to inspire action), and is specific and measurable. 

For example, using this approach I would rewrite two of the example goals generated in Step 1 in the following way: 

  • Original statement: Get leaner and healthier
  • New statement: Lose 10kg to weigh X. 
  • Or, even better: Reduce waist to 28” at 7% body fat with defined abs.
  • Original statement: Learn to dance salsa.
  • New statement: Become an intermediate grade level salsa dancer.

Notice how adding specific detail to the goal clarifies the picture and makes it easier to measure success. While some of the goals I generated in Step 1 would be perfectly fine as is, I go through the entire list and rewrite the ones that are too vague. This process also forces me to add a reality check to my emotional dream, i.e. to go after something that I truly believe is attainable within the time frame of one year.

Step 4: Refinement

Now, I have a list of 15 or so goals that are highly specific, get me genuinely excited when I think about achieving them, and are categorized into 5 or 6 areas. 

As this is a list that I would need to read often and memorize, I have learnt from experience that the life categories become a hinderence to that process and need to be dropped. Instead, all goals are sifted into two lists: Professional, and Personal. Stuff that helps my career move forward is Professional. Everything else is personal by default.

Next- and this is the hard part- the list actually needs to be pruned a bit. Trying to store a list of 15 items in your head is difficult at best, and having too many goals can also take away from the sense of importance that the list is designed to generate. To combat this, I force myself to prioritize the goals in each category, and elimate a few until I am left with a very strong set of 10 goals. (OK, this year I cheated and went with 12). Ideally, these should be equally split between Professional and Personal targets, or at most one could have 1-2 more of the one type over the other.

That’s it! From the initial session, along with two subsequent reviews to double check that I am 100% satisfied with the list, my time investment is usually around 2 hours.

Step 5: Creating Commitment

It’s no good to do this exercise, write down your goals, and then forget about them. I believe that constant revision and interim goal setting is absolutely necessary to stay on track.

So, armed with the list of annual goals, it’s time to break them down into 60-90 day “short term” goal setting periods, depending on what makes more sense for me at that time (usually, I go after 90 day periods). So for example, I would create a “3 Month Goals” list, that would re-analyze my annual list, pick what is most important for the next 3 months (not all goals need be on it), and reframe them into achievable milestones. To continue from the example above:

  • Annual goal: Reduce waist to 28” at 7% body fat
  • 3 month goal: Reduce waist to 32” at 12% body fat
  • Annual goal: Become intermediate grade level salsa dancer
  • 3 month goal: Start weekly salsa classes and memorize beginner steps

The “short term” list should always contain less items than the annual list (e.g. 6-9); this breeds greater focus on a few important things. Moreover, having a “short term” list allows me to reward myself at more frequent intervals throughout the year if and when I achieve a target, and ultimately keeps me on track to those big, exciting, annual goals.

Once I have finalized my “Annual” and “Short Term” goal list, I write it down somewhere that’s easy to recall, such as putting a note in my bedside drawer and having an electronic copy on my phone. Upon waking every morning and before going to bed each night, I read through the list and briefly visualize the outcome of each target. This process ensures that my goals are top of mind and that I can’t ignore them. This is a seriously motivating force.

Okay, perhaps this method is not exactly simple (and it will improve with time), but I think it works for me. What are your thoughts on my approach?

Good luck with your goal setting and all the best for 2013!

On Reflection and Self Analysis

A little while ago I celebrated my birthday, and it got me thinking.

We’re getting older all the time, but birthdays just make it more official- they help us to keep score of our lives in a sense. I think that birthdays are a perfect time to take stock of one’s life and ruminate on the year gone by and ponder the year to come. To me, this exercise helps me to refocus, repurpose, and redefine who I’d like to be at this new milestone. After all, life is a process of continual evolution, isn’t it?

Here is an outline the exercise that I planned and went through this weekend. 

Section 1: Key Area Checks

Begin by asking: “On a scale of 1 to 3, how did I do in each of these areas over the last year?”

1.1. Mental stimulation and general mindset?
1.2. Health and body?
1.3. Career progress?
1.4. Social (relationships, friends, family)?
1.5. Personal finances?

(I use a short scale of 1 to 3 meaning poor/decent/great as it’s a lot simpler to get an accurate estimate of how one really feels).

Once each area is rated, go on to review each area and ask:

- Was this an improvement over the previous year?
- What one thing can I do to improve this area moving forward? (Oftentimes, just one thing can make a significant difference).

Next up, it’s time to see where I went wrong.

Section 2: Negative Experiences

Here are the questions I asked:

2.1. What was my biggest mistake this year?
2.2. What was my biggest setback? What caused it?
2.3. What new negative habits did I form, if any?

Once those things are actually identified and written down, it becomes so much easier to learn from mistakes and take steps to avoid (or lower the risk of) those situations in future.

Finally, it’s always best to end things on a positive note.

Section 3: Positive Experiences

And the questions are:

3.1. What achievement made me happiest in the last year?
3.2. What is my fondest memory of the last year?
3.3. What new positive habits did I form?
3.4. What am I most grateful for?

Although very simple, this little exercise provides useful closure on a year past and paves the way for a frank internal conversation on deciding how to spend the next twelve months. 

This post was focused on self-reflection, so I will save my thoughts on planning ahead for another day. 

If you’re into this sort of thing, I strongly recommend that you check out Michael Hyatt’s fantastic blog post, Seven Questions to Ask About Last Year.

Hiring for Startups: 10 Clear Markers For a Great Fit

Building a strong team is one of the most important directives of a founder. There are many facets to this, but the most obvious and beneficial one is hiring the right people. 

We’ve recently made some new hires at Personera, and the process made me aware of a couple of key “go/no-go” markers that show themselves again and again. So what are some of the strikingly common as well as more nuanced factors when deciding if a candidate is a good fit?

This is my litmus test:

Positive Markers (“Go”)

  1. Smart and motivated: This is needs to be determined right at the starting gate. Any good team member is going to need to be smart because of the fast pace of a learning that takes place in a startup, and their motivation level will influence their ability to persist through the oftentimes tough three to six month beginning period to see what comes next, not to mention giving them an important sense of pride in their work.
  2. Extremely keen to join company: This is more important that people think. When a candidate is genuinely excited about a company’s product, or people, or both, that passion leads to much a better fit and sense of stickability with the startup over time.
  3. Has something to prove: The best startup team members always have a deep desire to prove something (either to themselves or to others), build something amazing, or leave a special mark on the world. They want to stand out from the crowd and escape business as usual. Over time, this defining characteristic is often the difference between a good outcome versus a great outcome when choosing a new team member.
  4. Likes working in small teams: Small teams allow for open and fast communication, lots of independence and responsibility (i.e. no handholding), and no office politics. The candidate should light up at the mention of that!
  5. Handles stress well: Startups can become very stressful at times. I’m not an advocate of keeping things insane all the time (or else people will go insane), but from time to time teams need to work weekends, weeknights, and deal with highly stressed out managers or (worse) customers. This can easily push somebody who has an anxious personality over the edge, so I think it’s important to bring people into a startup who are of a generally calm demeanor and don’t allow undue stress to shut down their nervous systems, so to speak.

Negative Markers (“No-go”)

  1. Focuses on shiny qualifications: There’s nothing worse than an interview where a candidate who wants to talk more about their degrees, course qualifications, and previous titles than what they actually do, or have accomplished with their work. This can also be a telling clue as to where their sense of professional pride stems from, and while not necessarily a bad thing for the person, this is definitely not a good thing for the startup.
  2. Debates contract minutiae: When a candidate wants to get into detail about contractual stipulations around things like office hours, leave, overtime (seriously?) and performance management policy (etc), I see red flags going up all over the place. Startup attorneys often write up employment contracts to favor that favor the company in the event of a labour dispute. If the candidate is truly ready to join the company, they will probably realize that (a) none of those things are likely to be managed and tracked to the letter of the contract anyway, (b) they will work as hard as they need to be a valuable member of the team and pursue the vision, and (c) a startup is not a big corporation. 
  3. No private projects to speak of: A candidate who has no side “pet” projects (past or present) to discuss is a concern, because that may show a certain lack of curiosity and personal passion in the candidate’s work. This mentality is needed for team members to think of innovative ideas to contribute to their area of the business, as opposed to just doing the work set out before them.
  4. Believes age equals entitlement: I am all about experience, capability, and delivery- and this is completely independent of a person’s age. Age can of course naturally lead to or correlate with these things (for most people maturity and experience takes time to develop), but when age alone is seen to be guarantee of seniority or entitlement, it’s cause for instant disqualification in my book.
  5. Existing staff feel uneasy: The social IQ of a team far exceeds that of the CEO or manager in charge. When a team member (or members) feels a little uneasy about bringing a new candidate on board, it’s best to take their concerns very seriously and reconsider the decision to hire. More often than not, the team will be right. This can very hard to do in situations where the hiring manager likes the candidate, and the person really wants to join the company. Hiring isn’t always easy.

I hope that this list of markers helps you to hire better. And remember, even with the best of checklists, there’s just no substitute for trusting your gut. 

Good luck and good team building!

The Importance of Priorities (How To Take Charge of Your Life)

I have noticed my life becoming increasingly busy lately, to the point where I someties feel like throwing my hands up in despair at all the things competing for my attention on a daily basis. The phone keeps ringing (and when I don’t answer, voicemails pile up). Hundreds of emails pour in. Somebody always seems to be waiting on me for something or other.

I know that I am far from alone in this department. In fact, I think that getting “out of control busy” is possibly a normal path of career growth, and is to be expected to happen to all motivated individuals (I’m looking at you, reader of this blog) who take on a lot of responsibilities at some time in their life. And as we get older, personal responsibilities seem to pile up right alongside the burgeoning amount of work demands.

I have been spending plenty of time thinking about this recently, and have come to a few (fairly obvious) conclusions:

  1. Things aren’t going to become less stressful on their own. The moment I move something off my plate, something new will be there to replace it.
  2. Efficient and effective working methods aren’t enough. Productivity hacks and systems like GTD are part of the solution, not the solution themselves.
  3. To remain sane, avoid burnout and continue to make progress, learn to operate calmly and stay cool amid constant chaos.

When multiple things are competing for our attention and pulling us in different directions on a daily basis, we face a choice of either becoming a victim of the chaos, or the master of it. To me, becoming a victim means watching your time evaporate day after day, progress hitting a plateau, and allowing generally negative thought processes to set in. In a busy world, if you aren’t sure what to do or work on next, somebody else will fill the gap and decide for you.

The path to conquering a chaotic schedule is to set clear priorities, and relentlessly stick to them. Begin by asking yourself tough questions like “What is really important here?” and “What am I unwilling to compromise on?”, and a powerful list quickly develops. Next, the list can be focused further by reviewing your upcoming goals and protecting your path to achieving them.

For example, here is a list of personal priorities to consider:

  • Health (diet, exercise, etc)
  • Family
  • Love and relationships
  • Learning new things
  • Saving money
  • Traveling
  • Spending time with friends 
  • …etc

And here is a list of business priorities to consider:

  • Sales
  • Budgeting
  • Recruiting
  • Leading the team
  • Project management
  • Admin
  • Getting help on certain projects
  • …etc

The application of this rule works in different ways for different people. I like to think in terms of monthly and daily priorities, and manage my to-do list accordingly. In any given month, I try to protect top 5 items from my personal and professional list as much as possible. I don’t always succeed at this, but awareness and clear direction is seventy percent of the battle. It’s always a huge temptation to decide to take on 20 different things in one day, but one has to realize that “If everything is critical, nothing is critical”, and plan accordingly. As much as we can logically split personal and business matters in our head, we only have one life and need to find a way to effectively combine the two.

As for all the other things to do, they usually have a way of taking care of themselves eventually. The key thing is that the fundamentals were looked after first, before the fiddling over the stacks of relative minutia could take over. When working at the fundamentals and getting those out of the way first, we can’t afford to let ourselves sweat over the small stuff.

Every day, remind yourself of your priorities, and why they exist. This will help you to control your life, as opposed to letting the circumstances of your life control you. There’s no comfort or salvation in making excuses. Setting sound priorities and sticking to them is a surefire way to create order amid chaos, reduce daily stress, and galvanize your ability to accomplish that which is important to you.

How do you cope with busyness, stress and many things competing for your attention at once? Let me know in the comments or drop me a line.

When Effectiveness Trumps Efficiency

In my last blog post, I discussed a system for eliminating bottlenecks and making startups more efficient (i.e. doing more faster) across every area of the organization. I did not at all delve into the concept of “effectiveness”, as contrasted with that of “efficiency”.

To me, efficiency is all about how you go about getting things done, whereas effectiveness deals with a entirely different subject: what it is that you choose to do.

When I was in high school, I had an exceptional Physics tutor who would constantly tell his students to “work smart, not hard” and “be effective” with our learning methods. He showed us alternative methods of studying and problem solving that were dramatically faster than the popular methods being taught in most schools, as a result his students consistently outperformed others.

This simple truth applies to just about any endeavour- from learning a language, to losing weight, to running a startup. 

With resources usually being scarce in a fast growing startup company, one of the greatest risks that they face is doing the wrong things very well, without knowing that those activities are adding little value to the company.

Becoming effective requires a combination of trial and error, learning from others’ experiences, and most of all critical, often stomach wrenching thinking on the part of the individual or team involved.

Once a month, it would be useful for the founders and team to go through this Q&A exercise aimed at seeking greater effectiveness:

A. Elimination

  1. What activities can we stop doing immediately that will have little impact on our company goals?
  2. Do we need to change expectations of any customers, or fire any customers that are taking advantage of us?
  3. Is everybody working on something critical? If not, why not?
  4. Are we paying for any services that we don’t need?

B. Initiation

  1. Do we need to invest in any new software to help our business?
  2. Should we hire a new team member to fulfill a specific role?
  3. Are we missing a value-adding activity that our peers are doing? What?
  4. Does anybody need to go for training to learn a new skill that will be beneficial?

Every time, try to table a set of action items, starting with at least one, with a definitive deadline to implementation. Performing this exercise would be like taking a consultant’s view of your own organization. And who better to improve a company than those most familiar with it?

Often, improvement stems from reexamining our basic assumptions and turning them inside out to see what we end up with. It’s a well known fact that effective people (and teams) are highly capable of achieving greater results with fewer resources.

As I mentioned earlier on, this way of thinking applies as much to one’s personal life as it does to business. Periodically, we all need to stop and ask ourselves, “Why am I doing this?”.

Martial arts legend Bruce Lee epitomized a person seeking to be effective in everything he did. (His entire martial arts philosophy of Jeet Kun Do was premised on a fluid style that borrowed whatever worked from other disciplines and discarded the rest). Here are two of my favourite quote of his to drive the point home:

"It’s not the daily increase but daily decrease. Hack away at the unessential."


"Defeat is a state of mind. No one is ever defeated until defeat has been accepted as reality. To me, defeat in anything is merely temporary, and its punishment is but an urge for me to greater effort to achieve my goal. Defeat simply tells me that something is wrong in my doing; it is a path leading to success and truth."

Eliminating Bottlenecks to Increase Startup Efficiency

The greatest challenge that every startup must face is the constant pressure of managing limited resources. Regardless of whether that resource is people, money or time, there is usually a known, fixed limit as to what is going to be available to achieve the next set of goals. 

For early stage startups, inability to surmount this challenge can mean the end of the company; in later stage and even successful startups, sub-optimal resource management will waste time, frustrate staff and customers, and hurt profitability.

The founders of the well known startup accelerator TechStars released a book in 2010 titled “Do More Faster”, which essentially sums up the operating mandate of every small startup in existence. So, with this in mind, a question I have often asked myself is: “How?”

The answer is not to work harder- are we not all working incredibly hard already? If I am able to process 50 emails in 15 minutes, then spending 30 minutes processing email will only get me through 100. I might be doing “more”, but I am not actually doing more with less and fulfilling my goal of “do more faster”. This simple logic applies to just about any startup activity, be that working with customers, releasing products, managing admin, etc. 

While some of the answers to this fundamental question might feel intuitive to many entrepreneurs and managers, I have had the best results by applying a logical framework to help me try to solve the problem. In search of answers, I dusted off a book that I read in university and decided to try and apply the principles in my own company. (Side note: I’m constantly reminded by that old saying, the value of a book is not in what the author chose to put into the pages, it’s what you chose to take from the pages and put into your life). The name of the book is “The Goal”, written by Eliyahu M. Goldratt, who is a legend within engineering management and supply chain circles worldwide. It’s a brilliantly written business book structured as a fictional novel, and I highly recommend it to just about everybody.

The premise of the book is very simple, and its method for improving an organization can summarized by the following questions:

1. What is the goal?

2. What is the single greatest bottleneck right now in the process of achieving that goal?

There is a lot more here than meets the eye (which is why you should read the book), but I will try to deconstruct this a little further with a simple startup Q&A example. 

  • Q (mentor): What is the goal?
  • A (manager): I can’t get through all my customer inquiries. Every day, the questions from various customers are just piling up, and the time spent on email is preventing me from doing more work. I need to figure out how to answer these questions faster.
  • Q (mentor): Is the goal really to answer more email? What does that accomplish- what is the end goal?
  • A (manager): The goal is to answer customers’ questions as quickly as possible, and make them happy.
  • Q (mentor): Then that is your goal. What is the main thing holding this process up right now? What is the bottleneck?
  • A (manager): I get too much email to respond to. I suppose I am the bottleneck- I don’t have enough time…
  • Q (mentor): How can you open up this bottleneck? Can anything at all be done?
  • A (manager): I’m not sure. There are so many daily emails and only I know how to answer them. 
  • Q (mentor): But can anything be done to open up the bottleneck, even a little bit?
  • A (manager): I suppose that I could start recording common things that customers ask for, and then write publish a FAQ that new customers can check before emailing me. This would free up some time.
  • Q (mentor): Boom! So what are you waiting for?

This simple, clear style of investigative dialogue can be applied to any challenge where one needs to deal with limited resources. Note that it is essential to address core issue being faced, and not to try to get tied up on the “hamster wheel” of addressing superficial symptoms or byproducts it causes (aka “damage control”). Another crucial aspect of the method is to remember to ask the “right now” part of the question, as bottlenecks in a system are constantly changing, so clearing bottlenecks and “doing more faster” is a really a process of ongoing improvement. With yesterday’s bottleneck eliminated, tomorrow will just present a new one (but hopefully by then things are moving a more smoothly). And, remember, only try to address one bottleneck at a time.

Goldratt coined his method as the “Theory of Constraints" (TOC), defining a constraint as "Anything that limits a system from achieving more of its goal".

This seemingly simple theory has had incredibly successful application to manufacturing and process oriented environments for almost 30 years. It can be pretty powerful when applied to startups too.

The application of TOC in our startup has been simple, structured, and effective.

Here is our method.

1. Define the System

A startup is just a system, comprised of different parts. (In business school they prefer to talk about the company value chain, but I digress). Define the different functional parts that matter most to the organization, i.e. where most of the resources (people, time) are being consumed. 

Some example areas are: Sales & Marketing (getting new customers), Account Management (delighting existing customers), Operations (managing daily work and necessary customer activities), Software Development (building and deploying product), and Financial Management (managing accounts, debtors and creditors).

Every startup is different, so list the areas that matter to your organization. I suggest putting this into a spreadsheet as different column headings. Underneath that, define the singular goal of every one of those functions.

2. Identify the Bottlenecks

For each company function, take the time to analyze and identify where the greatest bottleneck exists right now. If the constraint ends up being a person’s time, try to dig deeper to figure out what tasks are chewing up a disproportionate amount their time.

Some examples of bottlenecks from our past experience are:

  • Sales & Marketing: Repeating the same sales messages to prospects in writing or verbally due to lack of effective collateral.
  • Account Management: Repetitive, high volume email to a variety of business and technical questions.
  • Operations: Poor visibility on what everybody is doing forces management to ask too many questions and interrupt staff often, who become unclear on daily priorities.
  • Software Development: Implementing a new customer installation involves many time consuming steps on our side.
  • Financial Management: One person in charge of all payments and collections but does not have time to stay on top of it.

I suggest adding a dedicated Bottleneck row to the spreadsheet, so that a note can be made under each function column.

3. Identify the Solutions

Once the bottlenecks for each major area are identified, try to figure out practical steps that can be taken to eliminate, or free up the bottleneck. Following on from the example above, here are some of the past solutions listed to those problems:

  • Sales & Marketing: Develop marketing collateral material to leave with prospects after a sales meeting.
  • Account Management: Capture common questions and publish a detailed, easy to use FAQ for customers. Better yet, create a customer service portal with how-to guides, videos, and all manner of help resources.
  • Operations: Implement a system or tool that makes everybody’s work tasks and priorities transparent to the entire team.
  • Software Development: Focus the next wave of software development on automating deployment of the existing platform (as opposed to adding new features).
  • Financial Management: Have a different staff member help the individual keep track of creditors and debtors; and bug them when something needs to be done.

Solutions can be added to the spreadsheet as an additional row below the Bottlenecks row.

4. Review Progress

As with all initiatives, for this to work there needs to be a consistent process of review in order to maintain accountability and momentum.

I recommend that the senior management team of a company do this jointly every two weeks. During review sessions, managers should commit to when they expect the solution to a particular bottleneck to be completed, and this can be noted for subsequent review.

Over time, old bottlenecks will be deleted off the spreadsheet and replaced with new ones that arise. These meetings tend to be very rewarding, because after a while the progress achieved by following this process becomes obvious to all involved.

When dealing with the day to day volume of work to manage it’s all too easy to ignore this method for weeks and months, trying to make that metaphorical hamster wheel spin faster and faster. It took me a long time to fully understand what a waste of time that can be. 

To truly address the goal of achieving more with less, or doing more faster, and creating sustainable, long term performance gains I believe that constantly improving processes and eliminating bottlenecks holds the real key to startup efficiency. And that makes sense to the bottom line.

How to Divide Equity Among Partners in a Startup

Every entrepreneur needs to address this question at some point. Figuring out how to best divide equity in a new venture is one of the most critical decisions to take early on, as it has the longest lasting implications.

Fundamentally, equity means ownership. And in any venture, ownership matters. I believe that in my career thus far I’ve managed to get it wrong and get it right, and sometimes end up somewhere in between. This post stems purely from my personal lessons learned, along with some external observations to round out my recommendations.

When dividing equity among co-founders, two key questions must be addressed:

  1. How much equity does each person get?
  2. What happens if somebody doesn’t pull their weight, or abandons the project?

I will delve into each question separately.

How much equity does each person get?

I believe that the amount of equity that each partner receives should directly reflect the size of their contribution to the venture. Contributions (or value add) can be made in three main ways, namely:

  1. Operational skill
  2. Time and energy
  3. Money

Operational skill covers the role played by the particular co-founders. For example, in a tech startup, key roles could be sales and marketing, software development, and product design. Or in a restaurant, there would be a chef and a manager. In many startups, people have to take on multiple roles at the same time.

So to determine the value of the operational skills being added, the partners should assess the intended roles of each party as well as their skill level, and predict the impact that this would have on the venture. For example, a salesperson may be crucial to landing key deals, or a developer may be crucial in building an initial prototype to sell. The size and nature of the value add per person will vary from project to project. This would need to be thrashed out internally until a common view is developed.

A premium (i.e. increased equity stake) should definitely be added for the person fulfilling the role of Project Leader or CEO, and every venture needs a leading CEO character. A startup where this role is not clearly defined and supported by all parties is risking it’s future for a number of reasons to lengthy to get into in this post.

Time and energy refers to the physical time commitment of each co-founder to the project. Often, this is not as easy as “we will all do this full-time”, nice as that may sound. It’s possible that one partner would work on the project after work, or only on weekends, while the other(s) may be doing it full-time. 

The time investment to be made by each partner (as well as when that could change) should be defined up-front, and factored into the equity split. For example, a highly experienced salesperson founder would naturally receive a large equity stake in a business, however, if they are involved on a part-time basis while there is a software developer involved on a full-time basis, the developer’s stake should probably be greater. And vice versa.

Money can be contributed to the venture in two very simple ways. The first is that a co-founder is making a cash investment in the project. When a commitment to invest money is being made, I believe that the co-founder investing the money should propose the terms and valuation that he believes is fair, and the other partners can hammer out the negotiation. To keep everybody honest and the deal feeling fair, all parties should be allowed to invest at that decided valuation at that point in time.

The second way that money can be contributed to a venture is when a co-founder is saving the project cash by working for no salary. This situation should only affect the partner’s stake when they are doing this while working substantial hours (e.g. 18+ hours per week), not for part-time involvement as that contribution can be assessed based on skilled value add only. 

The final area that can affect how co-founders divide equity is the concept of who was there first. This topic always comes up, and it can take on two different forms, specifically:

  1. It was my idea.
  2. I have made progress on my own but need to bring in partners.

People who try to push the “it was my idea” line of reasoning as a means to get a larger stake in a venture need to be avoided. There is very, very little value in an idea on its own. The blood, sweat, tears and ultimate rewards come from execution. If the originator of the idea is bringing special domain knowledge to the project, then their contribution can be assessed under the basis of operational skill, as discussed earlier. Nobody should ever receive a founding equity premium (i.e. a larger stake) on the basis of coming up with an idea first.

On the other hand, if somebody had an idea and tried to start executing on it on their own before deciding to approach partners, that is a different story. In these cases, the co-founders should asses how much progress that partner achieved and where that puts the project in terms of traction and momentum. If the project has indeed progressed beyond ground zero and is out of the starting blocks, then it would be fair that the original founding partner receive some sort of premium for that effort.

Now that we have a decision framework for determining value add by each co-founder and dividing equity in the venture, we need to address the elephant in the room that is often ignored by co-founders starting out: what if a partner is no good, or if a partner quits?

Both of these fears regularly become a reality for new ventures! And it far more common among people that have never worked closely together for a meaningful period of time before (which happens more often than not).

This is where the concept of the “golden handcuff” becomes very useful. Co-founders should be “handcuffed” to their ventures, i.e. there should be a strong incentive to keep them fully involved. A good mechanism to manage this process is founder vesting. Basically, vesting means that partners need to earn their equity over a period of time, and stand to lose their equity if they leave the venture. Generally speaking, all vesting structures in new ventures should allow for accelerated vesting if the venture is sold before the partners’ vesting periods are up (i.e. they get to reap the value of selling their entire stake at time of sale).

Vesting structures can be pretty simple or extremely complicated. 

A basic structure could be: 50% vested up-front and 50% vested in total at the end of 4 years, so if the partner left before 4 years they would lose half their stake. 

I believe in taking a more nuanced approach to better manage the risks associated in dealing with co-founders. Here is my proposed vesting structure for a new project, fully explained:

- Vesting period: 36 months (3 years is adequate time for partners to prove their commitment).

- Up-front vesting: 10-25% of total stake (this gives each partner a strong sense of ownership in the beginning, which is important in motivating them to make the venture succeed, and it also recognizes their willingness to seriously commit to a new project).

- Vesting method for remaining equity: 1/36th of partner equity vested every month (this is a fair way to incentivize continued commitment with continued reward, as opposed to an all or nothing approach).

- Probation period before up-front vesting is recognized: 3 months. (The 3 month period provides the co-founders enough time to work together to get a sense of team dynamics, commitment and value being added).

The last point around the “probation period” requires more explanation, as it links back to the question I posed earlier: “What if a partner is no good?”. A partner can be no good for a venture for a number of reasons, such as:

  • They are difficult to work with.
  • They are not putting in the hours/pulling their weight.
  • They are not as skilled as the co-founders initially believed and cannot deliver the productivity and results expected when the project was started.

As in hiring new employees, the operational value and viability of a partner in a startup can be assessed fairly quickly. 

Then why do so many co-founders charge into equity splits and end up with partners holding on to stakes that they (the other partners) are not happy with, you ask? Well, I believe it’s because co-founders are often blinded by the romance and enthusiasm of a new project and see the world through rose tinted lenses, and as such would rather avoid these painful “what if” discussions with their partners.

The inclusion of a probation period takes this significant risk into account. At the end of the 3 month probation period (or sooner), a decision can be made as to whether every co-founder will proceed in their envisioned roles, or if somebody needs to be cut from the team, and not receive any equity at all (except if they have invested cash already, in which case the cash should either be returned or the co-founder should receive the pro-rata amount of equity deserved for the investment to date). Unfortunately, this is a lousy thing for the person that is dropped (if such an event happens), but all founders must take this risk, and it ensures fairness and alignment among the team, placing the best interests of the venture at heart. 

If the co-founders feel that a partner is not living up to expectations, the manner in which I propose that the decision be made is by a simple majority vote. Specifically, if more than say, 50% (exact amount can change depending on number of partners) of the venture’s owners (by equity value, not number) vote a partner out before the end of the probation period, then that person must leave.

I further believe that this system should remain in place even after the probation period has ended, i.e. the majority shareholders should be able to vote a co-founder out of the business, however, that co-founder would be entitled to keep (or sell) their equity vested up to that point. This additional mechanism ensures that co-founders keep pulling their weight and adding the expected amount of value to the venture on an ongoing basis. Remember, without such a clause in place the alternative for the remaining co-founders when faced with a non-performing partner would be to fire them but have them entitled to hold on to all or most of their equity in the venture.

If a partner is forced to exit the venture, the leftover equity, now unassigned, can be dealt with in a variety of ways, such as being earmarked for a new partner or an employee share pool, however the easiest method is for the leftover equity to be split pro-rata among the remaining active partners.

In teams of two where equity is divided 50/50 (a split I don’t often recommend) then voting somebody off the team so to speak does not make any sense. In this scenario, the unhappy party should have enough guts and sense to realize quickly that the partnership isn’t going to work out, and abandon the project completely or restart it on their own.

I realize that this is a sobering view on how to divide equity among co-founders in new ventures, but it is the product of years of experience and many lessons learned. When applied properly, this system would be very fair for all co-founders, leading to better alignment and increasing a venture’s chances of success.

I hope that this post was helpful. As always, I’m interested to hear your thoughts on this topic.

How To Manage Projects with More Than One Person

My last post on side projects turned out to be very popular, so I thought I’d continue the series with this follow up post.

We have all had our fair share of projects to deal with in every aspect of our working lives. In many projects, we are not working alone (nor should we be). The addition of a partner can be an excellent force due to enhanced motivation and sharing of work load, but it can also bring communication, accountability and planning difficulties which at worst can destroy a project.

After plenty of trial and error, I have begun following a system that keeps things simple and moving forward all the time. This approach will work for professional “on the job” projects as well as side projects of any sort. I use it to manage all of my small and large projects at work and at home, and this system easily scales to support more team members (within reason).

What I am about to describe is not a project management methodology (there are plenty of good ones), but rather an effective, step by step “how to” system of actions, dependables, and available tools. Best of all, this system works just as well when working with people remotely.

When beginning a new project with someone, here are some of the key questions commonly wondered about:

- What are we trying to achieve?
- What is the scope of work?
- How can we easily prioritize the work as we go?
- How do I know what the other person is working on?
- How will we stay accountable?
- How do we make all this easy to track? I am busy enough as it is.

Let’s begin.

Phase 1: Starting and defining the project

Every project should begin with a brief, 1-2 page “scope” document agreed upon by all parties. As it may change over time, I recommend using Google Docs.

In a new Google Document, give the project a name, title the document “<project name> Scope Document”, list the partners and when it was last edited and by whom (this is useful to be able to see in the document).

Next, add and number the major headings to the document that describe what the project is about, what the goals are, and the high level plan to succeed. Here are my typical headings:

1. Project Overview (2 sentences on what this is all about.)
2. Problem (What is the problem? Why does this project need to exist?)
3. Solution Description (How will this project solve the problem? Describe it in a few sentences.)
4. Goals and Time Frame (What are the specific goals? By when must they be achieved?)
5. Resources Required (What may be needed in terms of people, tools, time and money.)
6. Roles (What is the responsibility and role of each partner? Note that projects can differ greatly in terms of effort required and nature of role of the different partners.)

The body of each description should be kept as brief and succinct as possible. Use of bullet points and tables is recommended. Remember, this is not a pitch to impress anybody- it is a functional explanatory document for and your partner(s) to refer back to.

The next step is to better define the short-term milestones and resources required. I recommend using a new Google Spreadsheet for this.

In the first tab (name it “Milestones”), write out the major objectives that the project needs to accomplish over the next few weeks or months. Then group them according to expected completion. Depending on the size of the project, this can be split into weeks or months. For small projects I recommend doing this for the next 4 weeks ahead, and for larger ones 3 months ahead.

Next, create a new tab called “Resources”. For projects that require capital, create a basic monthly budget and add both a “Forecast” and “Actual” column to each month. (The actual column will only be updated when money actually changes hands). If no money is required, look back to the scope document and assess whether any other resources (e.g. help of a friend) will be needed and by when.

Once you’re all set up, on the same page as your partner and know what to go after, you are ready for Phase 2.

Phase 2: Managing work and making progress

This is the part when using a good tool makes all the difference. After trying plenty of project management tools over the years, I have to recommend one that beats the lot hands down: Trello. Trello has a killer combination of simplicity, visual understanding and functionality that other tools simply don’t match. And there is no learning curve either.

Register a new board for your project on and invite your partner. This is essentially a virtual whiteboard (a kanban board to be precise) where you can add lists (columns) and tasks (cells) that can be easily moved around. Names and number of lists vary from project to project depending on complexity, but here are the lists that I usually create right in the beginning, from left to right on the board:

General Backlog (all upcoming tasks not to be addressed immediately)
To-do: Sheraan (tasks I need to complete immediately/short term)
To-do: <Partner> (same as above for your partner)
Doing (tasks that are being worked on right now)
Done (completed tasks, awaiting team review)

Each task added to a list on the board should be succinctly described and always start with a verb, e.g. Research A, Prepare B, Start C, Write D, Contact E, Register F, Test G, etc. Try to avoid using the word “do” is it is often too vague and does not inspire specific action. Each task can have comments or files added to it if necessary. Once all of the tasks are on the board, take some time to prioritize them- highest at the top of the list and lowest at the bottom.

The Trello board is a work space that will constantly change and be updated. When you are working on a task, move it to the Doing list, then to Done when complete. As new ideas or issues pop up in the project, add new tasks to the board and reprioritize them all.

Note that I am specifically not mentioning email as a way to get things done. We are all snowed under with enough email as it is, and trying to use email to manage tasks in a side project is a sure fire way to cause confusion and lack of follow up.

Trello gives the team a fantastic way to immediately know what order to do things in, as well as full visibility on what each other are working on. As ground zero for management of the project, this workspace will be used and viewed on an ongoing basis.

Phase 3: Maintaining momentum and accountability

This is the most important Phase of managing a project successfully. The first step is to engender a sense of personal accountability by checking your project status often (I recommend at least once in 3 days). This involves a quick viewing of the Trello board to see what has changed and what hasn’t. If tasks are not moving across the board, your project is stalling and rapidly losing momentum. All parties need to be realistic about the need to achieve a certain rate of progress in order to succeed.

In order to foster strong communication and joint accountability, schedule a weekly one hour meeting with your partner that you can both stick to. Try not to move this meeting around as it can undermine commitment to the project. During this meeting, start by going over the tasks on the Done list in the Trello board and if satisfied, archive them so that they are removed from the board. Next, evaluate the priorities for the week ahead and adjust the board as necessary. This type of review session will make it very clear if the work is getting done.

At the last meeting in a month, perform an additional review of the monthly milestones Google spreadsheet to see how you have fared. Learn and adjust these as necessary. Then update the Trello board once more.

It is crucial that you physically review every work item completed during the week together as a team, and mark off completed items. It is woefully inadequate to simply discuss things without reviewing the written to-do items and milestones, as talk is often a cheap excuse for lack of effort and progress. This trap is especially easy to fall into when both parties have slacked off on their responsibilities. Remember, a light discussion about work not done may make both feel better, but it will kill a project. If you fall off the wagon so to speak, it’s much better to stare at that truth in the mirror, admit it, and get back on with it as soon as possible.

Make these meetings sacred. If one party can’t make it, reschedule it during a time that works for all. If one party misses a meeting twice in a row or doesn’t seem that interested, they need to restructure their role or be cut from the team.

If you keep repeating the process described in Phase 2 and Phase 3 over and over, it is guaranteed to produce real, ongoing results!

To recap, here is a summary of my project management process:

1. Write project scope document with specific overall goals. (Tool: Google Doc).
2. Define short term milestones; weekly or monthly depending on scope. (Tool: Google Spreadsheet).
3. Prepare project budget/resources needed, forecast and actual. (Tool: Google Spreadsheet).
4. Set up Trello board and add upcoming tasks. (Tool: Trello).
5. Use Trello board on an ongoing basis as work is done.
6. Attend weekly meetings to review and update Trello board, as well as project milestones and budget once a month. (Tool: Skype, phone, coffee shop, apartment).

Final thought

The greatest risk to any project usually is not a poor outcome, but instead a lack of any outcome at all due to abandonment. Most people don’t finish the projects (especially side projects) that they start. Before committing to a project with a partner be sure that both parties are motivated, dependable, and taking things seriously.

While it is no replacement for committed hard work, I do hope that the system I have described makes the process of executing your next project simpler, faster and more rewarding.

Making a Hobby out of Work: The Benefits of Small Side Projects

Most of us- entrepreneurs included- have a full-time job. This is the focus of our professional career for a particular point in time, and it demands our utmost dedicated application. For entrepreneurs, it’s the company that they have founded and need to lead. All of those customers, staff and shareholders are depending on them to deliver at the end of the day.

Motivated people have a penchant for choosing all manner of high intensity jobs for themselves. They thrive under pressure and work hours well beyond the regular cubicle dweller. Moreover, these types of people often love to work as well, or to be more specific, they love cramming productive things into their time. I suppose I fit into this category (at least on good days).

I find that the downside of this attitude toward work is that my main working objectives (the most important and urgent ones) have a tendency to swallow up all of my attention. Sometimes these projects are delightfully interesting, and other times they are tedious and complex- or worse- boring. The type of tasks on the to-do list for that week need to be done however, regardless of how one feels about them.

This brings me to the key question underpinning this post: what is the best way to deal with free time if we want to spend it doing something productive? Or to relax, let off some steam and exercise our brain without making it feel like work?

I often ask myself this type of question on the odd late evening after a long day at work (and usually with a nice red wine to accompany me), or weekend morning (fresh from a full night’s sleep), or on an airplane (where I am writing this post). I enjoy vegging out in front of the TV as much as the next guy, but sometimes there are just too many neurons firing at once to make that an enjoyable experience, so a sense of mental restlessness takes over.

At this point, the thought of responding to more incoming emails, or finishing that presentation, or finalizing that budget, or reviewing that contract (or a dozen other possibilities) present a mild headache that can wait until the next morning at the office when I’m in full swing “company mode” and all fired up. But the feeling of wanting to do something little and yet productive still lingers, much like a craving for a late night snack or an itch that you won’t feel satisfied until you scratch.

At these moments, I personally feel that reviewing the to-do list or inbox is a total mind killer and waste of time. It causes undue stress about things that need to be done soon, in moments when I don’t feel like I have the time (or energy or intensity) for doing them. So, how to flex your mind and have some fun at the same time? I have found that the magic solution lies in side projects.

This might seem like a no brainer revelation, but it’s taken me some time to really take this concept to heart. Side projects are wonderful. They are intended to provide meaningful, productive, self actualizing output while being fun, non-stressful, engaging and personally rewarding. Side projects are also an incredible way to utilize excess cognition and creative capacity while learning new things that make one a better person.

The key criteria for a good side project is the following:

  1. Has a defined, valuable outcome.
  2. Has a flexible due date or is ongoing.
  3. Is not critical to short term job performance.

While all criteria are fundamental, I think that number three is the most important, as this factor will determine if a project is net personal contributor of bad “distress" or good "eustress (what we are after). 

In my opinion there are 3 types of side projects that one can engage in:

  1. Professional, job related: e.g. a pet project for a department that you are not responsible for but want to help; a way to automate some of your repetitive tasks that you never get time to do during the day; a new filing system; a new email system; test driving the latest software app to help you in your job, etc.
  2. Professional, not job related: e.g. writing for an industry publication; advising a different company; joining a professional organization; working on a new invention; taking an online course; starting a pet project with some friends, etc.
  3. Personal: learning a new language; losing weight/getting fit; learning how to cook properly; writing a blog; building a model plane (or lego Death Star); doing community theatre; joining the local Toastmasters or Rotary Club; studying a liberal art for interest’s sake, etc. 

During a tough patch or plateau at work (i.e. your all consuming job), side projects can be a great tool for reminding yourself that being productive can be fun, and that you are capable of achieving wins when you put your mind to it. During the good times at work, side projects provide a stimulating outlet to let off steam while indulging your creative faculties.

The best part about side projects is that you determine what they ought to be. Over a period of months and years, these “little wins” will rack up alongside one’s main career focus and leave a nostalgic trail of rewarding outcomes for mere bits of spare time well spent.

My Top 6 Inspirational Movies of All Time

In addition to my love of books, I love watching movies too. My rule is to never watch anything that has scored under 7.0 on IMDB (although I make exceptions for the occasional sci-fi flick). 

The movies I tend to remember the longest and have the most meaningful impact on me are often highly inspirational ones. Without further ado, here is the list of my top 6 inspirational movies of all time- please enjoy!

1. Gattaca

In a dystopian genetically engineered future that is frighteningly plausible, people are judged according to their gene potential and little else. Natural born children (without genetic tampering) are shunned by society and only allowed to pursue the most menial jobs and careers. Ethan Hawke plays an imperfect young man who refuses to accept the status quo and embarks on a dream to become an astronaut, with the help of a genetically perfect Jude Law who is bitter about the system. This movie epitomizes the power of the human will to succeed against all odds.

2. Any Given Sunday

In this American Football story, an aging team coach (Al Pacino) and quarterback (Dennis Quad) are pitted against younger, hungry foes that seek to replace them. There’s plenty of action and all out sports play, but it is was this hugely inspirational speech by Al Pacino during the final game showdown that I’ll always remember:

3. Glengarry Glen Ross

This has been the quintessential salesman’s movie for the last 20 years. The entire dialogue heavy story revolves around a group of real estate salesmen who are struggling to meet their numbers before the end of a crucial month, and the lengths that they go to try and make a sale. Anybody who has ever been out on the road trying to close sales will be able to relate to this movie. At one point a senior manager (Alex Baldwin) walks in gives them a brutal pep talk that is unmissable:

4. The Shawshank Redemption

This movie revolves around a man (Tim Adams) who is wrongly convicted of a crime, then imprisoned for a lengthy sentence. During his time in prison, he makes a best friend (Morgan Freeman) who helps him make his time more worthwhile. In the end, he’s able to mould his destiny and find happiness in the toughest of conditions. This incredible film holds the rating for Number 1 movie of all time on IMDB. 

5. The Concert (Russian)

This movie is pure magic. It’s about a retired and disgraced (but brilliant) orchestra conductor who hasn’t worked in the music business since Communism fell. His former orchestra is in tatters, most now poor and out of the business completely. He manages to sneak a big shot to play in foreign country and sets about frantically rebuilding his orchestra and getting to the show before the Russian authorities catch up with his plan. This delightful piece of filmmaking reminded me how we can (and should) never escape our passions in life, for it is in passionate work where we are at our finest. See the trailer here:

6. Rocky

What can I say about the movie Rocky that hasn’t already been said? It’s the story of a soon to retire, down and out boxer who never made it big in his career, despite possessing some talent. One day, he gets a wild card shot at the world heavyweight champion that nobody takes seriously except for him. Well, we all know the rest of this story.

It was in this movie that Rocky, lying in bed and feeling crushed by the magnitude of the task ahead of him, uttered one of my favourite lines of all time: 

"I can’t beat him. But that don’t bother me. The only thing I want to do is to go the distance, that’s all. Because if that bell rings and I’m still standing, then I’m gonna know for the first time in my life, see, that I wasn’t just another bum from the neighborhood."

The Rocky movies consistently display how the person with the most heart can win, in spite of the largest of obstacles. Rocky is the ultimate people’s champion and there is more than enough to love about this movie.

In fact, the story of Sylvester Stallone and how the Rocky movie came into being is an incredibly inspiring too. Listen to it here:

Tony Robbins Shares Rocky’s Story by supergrowth11


David Shrigley, It’s All Going Very …, 2010

this explains startup life so well