Archives for category: Being a startup

Over the past 11 years, I’ve been involved with 3 start-ups:

  1. In 1999, while working for PricewaterhouseCoopers, a co-worker and I designed and built, a site where people could submit stock tips and we would track success/fail rates – and assign reputation points to the best “tipsters”. With the NASDAQ crash in April 2001, so went
  2. In 2007, while on vacation in Maui, my beloved partner and I conceived of a realtor reputation system called (still technically live but not ‘alive’), where clients of realtors could rate their experiences – good or bad. Unfortunately, as a group, realtors don’t want their clients being honest about their experiences, so our target customers were ultimately against us.
  3. In July 2010, Joanna and I decided to build, another user feedback system – this time targeted at aspiring writers – that enables readers to rate the quality of writing from a single page of a manuscript (you guessed it… page 99). We sincerely hope it’s a success story in the making…

In those 11 years, probably the biggest challenge for me, as an entrepreneur-in-training, has been working through disagreements between co-founders. It’s something that all co-founders will eventually face, so the goal should not be to avoid the inevitable, but to handle it in a way where everyone walks away feeling heard and supportive of the decision.

Compounding the challenge for me is the fact that my co-founder in 2 of the 3 above ventures is also my amazing partner in life, Joanna. And while many of you may have decided to part ways as start-up co-founders due to a conflict – and this is certainly an option even for life partners who run a business together – dealing with a business casualty can add significant strain to what is otherwise a loving personal relationship.

This post is about reflecting back on what has worked for me and what hasn’t, but I am most interested to read your suggestions for how to do it better.

Here are the most common conflict resolution options and outcomes in my own experience:

Option #1: Game of Chance

It’s possible to resolve a conflict using some form of chance, such as flipping a coin or playing ‘Rock, Paper, Scissors’.

  • Pros: Quick, easy to implement (providing both parties agree to use this form of conflict resolution).
  • Cons: It’s kind of like throwing your arms up – or giving up on your point of view without a fight.

Option #2: Art of Persuasion

This is where one co-founder tries to convince the other to come around on their point of view, and vice versa. From my experience, the intensity of the conversation can vary between completely calm and over-the-top-crazy-with-emotion (the former usually resulting in a better outcome for all). The key here is to really listen to the other party. You don’t get to speak until the other person has stated her point of view – and listening doesn’t mean formulating your response in your head as the other person speaks. You may also agree in advance that whoever feels strongest about the issue is the person whose solution is implemented, but this is easier said than done.

  • Pros: Likely more effective than flipping a coin because reason is used, both parties can come away feeling good about the solution.
  • Cons: Can be an exercise in debating skills, really only works if both co-founders are open to listening.

Option #3: Tell It to the Judge (or Democracy Rules)

If there are three co-founders and two are not in agreement, then the third can be the tie breaker, although the perception of alliances can create different problems for a team. A better option may be to present both sides of a conflict to someone who can act as a mediator and a judge – whereby both parties present their ‘case’ and then the judge makes her decision.

  • Pros: You’re not trying to convince each other, so it’s less of a debate.
  • Cons: It may be just as difficult to agree on an impartial judge.

Option #4: Breaking Up Is Hard to Do

It sounds extreme, but it happens. A conflict about one thing can be the symptom of a much bigger issue, and if neither co-founder is willing to give or explore other options for resolving the conflict, then sometimes this is the only possible solution.

  • Pros: No more conflicts to resolve.
  • Cons: Is holding onto your point of view really worth dropping a great business idea over?

I’ve tried the first three options with varying degrees of success, and for me, no one method of conflict resolution has worked consistently well. Yet option #2 is still probably my favourite because it usually results in both parties feeling pretty good about the solution – but it all rides on how well you listen and your ability to keep pride out of the discussion.

What little tricks for resolving conflicts have worked for you in your start-up? Any disaters?


… or without even knowing it, for that matter.

This post is about the recent launch of our start-up,, and an interesting phenomenon I first heard coined by Jason Roberts of TechZing fame (a podcast I highly recommend for tech entrepreneurs): “Luck Surface Area”. As I understand it, Jason believes that by putting yourself out there… blogging, podcasting, commenting in online discussions, and following up with every customer and user, you increase the likelihood of having a serendipitous moment. It’s a fun concept to consider – but perhaps less of a scientific occurrence than yet another example of the Law of Averages. Whatever your belief system, something very interesting happened on the day of our launch…

For a little context, our Web site (which lets published and unpublished writers upload page 99 of their book or manuscript and get immediate first-impression feedback from readers on the quality of their writing) was launched in beta on October 10th (10/10/10) to about 100 people who had signed up on our pre-launch landing page.

During our 2-week beta test period, I had tried [unsuccessfully] to get some initial traction on Hacker News by writing a few posts on this blog about launching a start up, building an audience, etc. My attempts were likely unsuccessful because just as we were preparing to launch, there was a glut of “Ask HN” submissions for Rate My Start-up that were seeing fewer vote-ups and fewer promotions to the HN home page. So much for serendipity.

I had mentioned my goal (and fast-becoming obsession, frankly) of writing something of value for the HN community and landing on the front-page to my partner – in business, life, and love – who is always supportive of my endeavours, crazy as they may be (thank you, Joanna!). She is also an amazing Web copywriter and agented fiction writer who always reviews my blog post titles for ‘click appeal’ (like sex appeal, but for… well, you know). So when she learned of my obsession, she decided to spend some time on Hacker News to see what all the fuss was about. And in the time that she spent reading a few posts, she responded to a simple request for help by a HN member named Shereef, who was looking for some copywriting tips for his start-up,

Being the generous person that she is, Joanna offered to help put together a brief list of recommendations that Shereef could implement on his site. But Shereef had no idea what he was about to receive. And with absolutely no expectations – and nary a mention of her work on to me – Joanna compiled a thoughtful and detailed list of best practices and recommendations on writing more effective copy for Shereef. I’m sure she thought that would be the end of it.

Fast forward about a week to October 26th… official launch day for – and which also happened to be Joanna’s birthday. We spent the day making sure that when we launched the site to the 2,100 people who left us their email addresses, there would be no user experience or technical glitches – having read enough horror stories about sites that managed to get some tech news big coverage but collapsed under the traffic pressure (oh, but what a problem to have!).

We sent out our launch email and posted to Twitter and then got ready to head out for a romantic birthday dinner. We came home after an evening of awesome food and wine and couldn’t help but take a quick look at our traffic using Google Analytics. To our astonishment, traffic had soared while we were out, with our site receiving over 2,000 visits in the time it takes to finish a 5-course meal.

Thanks to Shereef’s gracious acknowledgement of Joanna’s work, the HN post received 423 points and 120 comments in 24 hours, landing easily on the front page and staying there for a good stint… and Joanna’s PPT deck (that Shereef posted to SlideShare) saw more than 7,500 views in that period.

Post on Hacker News:

Joanna’s PowerPoint deck:

During the burst of activity on HN, Joanna received many requests for copywriting advice, and true to form, she’s making her way through a bunch of Web sites – despite being extremely busy with our own start-up and her day job as a senior Web copywriter for Intuit. She (and I) has also been fortunate to connect with some amazing people as a result of that one post – like Patrick McKenzie of Bingo Card Creator and Appointment Reminder.

Whether you call it karma or expanding your luck surface area, it’s clear to me that sometimes you can try too hard and miss out on letting good things happen. While I tried for weeks to think up creative ways to get some Hacker News love, Joanna was just herself and ended up with one of the biggest recent posts I’ve seen on HN about someone’s generosity.

Good things come from doing good deeds. It pays to be generous and help others out, because you never know who you’re helping, and it may come back to you many times over – in ways that you can’t even imagine.

Thanks, Joanna. I love you.


Well, we’re planning to launch this Tuesday, October 26. And we’re, um, exhausted. Our developer Steven has obviously been slaving away since receiving feedback from our “exclusive private beta” testers. And Lance has been forming new relationships with cool people, like some fine fellows over at AbeBooks and AnyNewBooks. I’ve been working on stuff like our first actual press release.

But we’re pretty jazzed about the amount of press we’ve already received without, well, ‘trying’. GalleyCat wrote about us, and the Guardian (UK) did a great article on us – as did The National in the middle east. Tons of bloggers have covered us – from editors to agents to writers to librarians. And CBC Radio here in Canada did about a minute on us… which is wicked-cool. Read the rest of this entry »

You make a product. You think it’s great. You launch it… and no one shows up. How’s a startup supposed to grow in an environment like that? – where you can build something useful that only 1/100,000 people are interested in? (Yay for early adopters! But every startup wishes it had more early adopters.)

It’s a problem we all have to face, of course. Attracting users is sort of hard. “If you build it, they will come” is simply not the case; and it’s never been the case – at least not since ye olde days when Kevin Costner had a career. No point in complaining, though. We just, as struggling startups, need to figure out a strategy to attract interest and/or get some press.

But even the old-fashioned problem-free path to press – throw money at a PR firm – won’t get a tech startup very far, necessarily. Michael Arrington’s been pretty vocal about sucky, annoying PR ‘stars’ who make rabid pitbulls look like Jedi masters. Press releases just feel dull. And, with success stories like Mint aside, old-school PR just isn’t cool enough or smart enough or ‘with it’ enough in the tech community to help startups get the blog coverage we need. Read the rest of this entry »

There’s a lot to the title of this blog post. To get anywhere near bootstrapping, first you need an idea. And there is no shortage of ideas. Recently it’s become apparent that a lot of smart people are happy to post their ideas for new businesses on popular sites like Hacker News. I grew up thinking that a good idea is precious, and that it must be kept hidden from others at all costs, until it’s ready to be launched to the world. But as the debate about ‘idea versus execution’ rages in small circles of would-be entrepreneurs, I’ve come around in my thinking… to where I believe a good idea is important, but the execution of that idea is what’s truly precious.

Finding an idea that you believe in… that is the hard part. How do you assess the quality of an idea? What makes something worth ‘believing in’? Read the rest of this entry »