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Protected: The best thing about hard things

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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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