Tag Archives: startup

The best thing about hard things

It has been just a couple days since our last board meeting and we were settling back into business as usual. And that’s when it hit me.

I would have never imagined that one of the most compelling, motivating and reassuring days of my life would have been when we were pushed into a corner, almost powerless, close to defeat and left only with a choice between overcoming insurmountable odds or packing up.

If you’re expecting this blog post about some company that came back from dead and turned it around into a billion dollar business, sorry to disappoint you. I am too impatient to wait and see what happens to LeadSift and then write about it when and if we’re successful, also frankly, I don’t care. It’s not the destination, it’s the journey. Although most smarter folks would wait to write this post until they make it through, I want to share a profound experience – at least to me, a first time founder.



The Startup Menace

In late 2012, we raised a sizable seed funding from some of the hottest names in Canada, been tech-crunched, signed a partnership with SalesForce, launched a premium app with HooteSuite, inked a few other partnerships with large agencies, had media flogging us and raving about us, people wanting to work with us and we were pounding out code like nobody’s business.




holy_shitAttack of the Business Model

The problem was… it was indeed no body’s business. Soon we realized our product would never scale, the press died down and we were left scurrying towards a… you guessed it… pivot. (Except that we didn’t call it that). We survived that storm, the board supported us through figuring out our shit and build, rinse, repeat.


After much effort and grind, we are currently at the best place we’ve ever been at. Customers want us, large enterprises return our calls and set up 2nd and 3rd and 4th meetings. They take our ideas and pass them on to their creative departments. They line up as pilots.


 Revenge of the Bank Balance

Except…. we’re out of money. And, after a couple failed tries and overall rookieness, we’re not winning any awards with our boards’ confidence. I think I experienced what it feels like, getting kicked in the nuts, at our last board meeting!


 Return of a Game Plan

Within the last week, we’ve had to lay off some very talented and some of our favourite folks, and, in spite of making quite meager salaries, take paycuts ourselves. We talked to the rest of the team to describe what we were up against and what our game plan was. We need to be super focused and our future depends on the timelines of some of the customers’ in our pipelines and other external things that we can’t always control. We’ve also realized that we should have done this a couple months ago. Sounds grim, right?


LeadSift Team Strikes Back


But I feel compelled at this point, to quote some of our teammates and employees reactions when we broke this news to them. Ranging from the one person wanting to keep helping us with LeadSift for free to another person insisting that he wants a paycut with the founders! Another founding member who had kids, family, house, the whole 9 yards of responsibility, after a few beers that night, came in next morning and kept reassuring us that he’s here till the end and he’ll do anything for LeadSift, anything. Among other things that day, he gave away his personal cell phone number to a client who runs a 24/7 call center, for customer support requests, to ensure no matter what, we do our best! We support our university by hiring students for research and our post doc student took some of the pressure off our shoulders and talked to the professors and the research assistants giving them the disappointing news. A co-founder, who just had a kid, offered to go off payroll and on parental leave to save money.


New Hope

You might know, that as egoistic over achieving startup people, we go through a lot of clashes.

But, we all came in the next day, stronger, more determined, more unified than I’ve ever seen the team. Everyone had their war paint on. Everyone was aligned on one goal, and one goal alone. Each and every move, strategy, discussion, no matter how doomed it should have been, seemed more pumped, hopeful, exciting, confident. A chance to prove ourselves, a chance for victory, a chance to not die a zombie but a plan to go out with a bang if needed.




There is absolutely no way, that with this team, this passion, this hard work and this loyalty and authenticity, we won’t see a win. And… come to think of it, this IS our win! Anything else, is just gravy.




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Feeling of can’t keep up

I am a start-up co-founder. I am also an egoistic, perfectionist control freak, borderline asshole (there’s some debate on which side of the border I am in). Often these alpha traits converge into a mash of anger and disappointment, overall a downward spiral where Over Achieving Requirements and Over Arching Deadlines rule your life.



Yep, I know you’ve been there too.

I don’t have answers on how to fix it. Yet, I know I’m not alone and neither are you. Since I’ve have been at this for nearly two years, there are some things that are sometimes successful at making it possible to live through it, with it… nay… conquer it. Or things that I hope to be reminded of those days when I’m going down the rabbit hole and this is short chronicle.

1. Trust your founding team and speak up right away and act right away. If your founding team has cracks… you’re not going to make it through. (Everyone’s heard this many times)

2. Take the tough decisions, fire, hire, add the new feature or don’t. Stop deliberating and going round in circles! Two meetings per feature, if a feature is brought up in the 3rd meeting, you could do better! (We’ve failed at this a handful of times and it’s caused us tons of grief)

3. Don’t dip your nose/hands in “everything” just because your life depends on it (yes, I agree your life does depend on it). You cannot control every aspect of a business and neither are you the best person for it. Against popular media, it’s never a one person company (nope, not even Steve Jobs) and without your team, you will not ship shit! (I am guilty of this where I try to keep my fingers in every pie expecting a sense of sanity/control, but I think I’m getting better)

4. Measure. We usually think things are much bleaker than they actually are because we’re disposed to being scared. (We once thought we were at the lowest point but we stepped back to realize we had 7 Fortune1000 clients in our funnel!)

5. Celebrate the wins, even the smallest ones. High five, get Chinese take out, get beer, get ice cream. Go out together and play cricket or paintball, get a bell in the office and ring it at every good news. (I have yet to try this but I REALLY want to, need buy-in from my co-founders.)

6. Breathe. Believe. Repeat.



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Ever been to a house where stairs creek, a tap stops leaking only if turned off a certain way and the corner window has a little crack which lets cold air in but the people living there put this fantastic decorative showpiece that blocks the stream and they’re proud of the genius behind it?

Yes, that is ownership.

It’s not always glorious, it’s a lot of hard work (shovel snow or pay for a overflowing toilet anyone?), it’s a lot of commitment and understanding. Yet, the best owners are the ones that thrive the challenges and come out proud and loving!

In a company, your team will always consist of very different kinds of people, (for tech companies, different = weird!) – someone’s wife had a bad day, someone started a new strict diet, someone had a fight with their parents, someone with loved one who’s very sick, or is in financial crisis! Your business will go through different kinds of challenges ranging from “no sales in a while” to “we ran out of water in the office”. You yourself will go through crisis and wonder, is this a real business, will this work, what if we don’t make more sales, what if my key person leaves, how long do I wait? It’s a LOT to deal with. If this a startup, there is a whole different level of instability as the icing.

Good ownership if when you can look forward to solving these problems everyday, you may not know the answers but you know your people, your team feels the same ownership as you do, you understand the subtleties, you love the high of doing something meaningful, you feel empowered,  you own the mistakes, you share the victories! You treat your company like a child, your child, which has some bad habits, some defects but you’ll do anything to fix it. And you’ll work as hard as needed. And you look forward to it. It’s not a challenge, it’s your life.


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Patience for Startups

“Have the courage to be impatient, the patience to be brave.” – When I first read this quote, I was much younger and I remember thinking to myself, this does not apply to me but I can see how it applies to grownups!

After years of reading The Letter, I have come to the point where I am grateful to Abe for so beautifully and poetically making me aware that I am not alone in this silent desperation.

LeadSift is at a stage where we must take bold steps and be most patient, both at the same moment. As a B2B enterprise software, we need to be fervent in contacting Fortune 500 companies and relentless in our patience as we move through their molluscan sales cycles. Crouch behind the trees with feline grace while breathlessly waiting for the moment we can sprint for the kill. Be ready to hear no’s because that’s where we’ll learn the most. Keep trying because we will hear a yes. It’s gut wrenching; for people who have never done sales, who have never dealt with enterprise bureaucracy, for them who take pride in weekly feature releases and working 18 hour days, for them who take pride in moving fast, for LeadSift, for me. Every moment spent waiting feels like breaths being sucked out of our lives.

Startups have two options, move lightening fast or fail. So this dichotomy feels very unsettling, painful. I don’t believe there is an easy way out but believing in the wisdom stops me from feeling like a helplessness headless chicken, enables me to gather the courage to be patient, to wait for another day, the right person, right time, so we can be brave when the moment arrives.

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