Biggest Fails of My Career
Biggest Fails of My Career
My first startup was stalled at 3 million ARR for five years.
So it basically took two to get to 3 million and then three it was stalled
there.
And then it wasn't like I wasn't doing anything.
I was trying stuff that were these huge initiatives and they were just
failing in like epic fashion.
And the first fail was something called Robly Authorized Partners.
My whole business, my whole first business, it was called Robly Email Marketing
And we were kind of picking up breadcrumbs off of the constant contact table.
We had this data mounting strategy and it worked to get us to 3 million and
then it stopped working.
Nothing that I tried could get this thing moving and the reason why really was
because
MailChimp was like had this free product that was amazing.
You know, it was just the most incredible company in the world.
In trying to do stuff that MailChimp wasn't doing, the first thing that I tried
was called
Robly Authorized Partners.
And what I thought was novel about it was if it was true that it actually
worked
and it sounds crazy to say it now, but like boots on the ground selling
software.
Like it was definitely the opposite of what MailChimp was doing.
It was probably a great play for like a very large scaling business.
They looked at this as a brand expense, you know, and they needed humans
walking this type
of person through how to use the software and whatever else and they got word
of mouth from
or whatever.
When you're a 3 million ARR SaaS, you need like positive unit economic customer
acquisition to grow
and that was not this at all.
There was like, it was the farthest thing from this.
You know, it took me a really long time and like we went on this big road trip,
spent a
ton of money on it and then, you know, it took me a really long time to realize
that.
That was horrible.
My second biggest failure, which was like the next thing that we tried, Diana
was doing
some consulting with me.
You know, it's like, well, why don't we go above MailChimp?
And she was working at this other place that killed it.
She thought they were going up even more and like leaving this gap.
I hired a bunch of engineers, spent a year building the software, like a
million dollars
of salaries or whatever.
Then we go to like launch it at this trade show called Traffic and Conversion.
They figure out what we were trying to sell.
Isaac Lazed Over.
Right.
Just like, I do not care.
And it became very clear that we were wrong.
10 other people already had this market above MailChimp.
The moment of the most pain, which like, I'm sure many people who build
software of
experience, which has made me so careful now in whatever I build,
is we just threw it away.
Like a year's worth of work just tossed it, which is terrible.
But like the silver lining and all that was I was emotionally devastated
because after the
first day, I'm like, no one cares.
Like no one cares.
Right.
Like, but then I'd ask people, what if I could give you email addresses of
people that were
on your website and didn't fill out a form?
Like, boom, like now I'm listening.
That motivated me so much more to try to figure out how to do this.
And then ultimately we did, and ultimately it was a great product.
Looking at people's facial expressions about what you're working on in your
target market,
it can just be so, so incredibly informative.
And then the last thing, you know, a lot of people might say I'm crazy for
saying this,
but like retention.com was an epic fail in 2023.
I thought that because we had honed down on this Shopify Plus audience in Klav
iyo and Yapo
and Recharge and all these people had so much success growing in that audience,
that a churn problem that we had would get effectively eliminated.
And we would be able to very quickly, like the sales velocity we have is
unbelievable.
I thought we were going to go from 15 to 50 million in a year and like it'd be
unicorn.
And I was so confident in this.
I made a docu series about it.
Like not only do we not do it, like we didn't even come close.
Like the goal was 50 million, we ended at 22.
You might say that, oh, it was still a really successful year, but like it's
kind of okay.
Like you shoot for the moon, you hit the stars.
When you declare to the world and call your shot that like something is going
to happen,
and you don't even close to get there, like that is a fail, in my opinion.
To be clear, failing does not, these days does not bother me that much.
I think that I've gotten much better at failing earlier, if that makes sense.
Like with this B2B thing, we've had 300 phone calls with people.
We're launching the UI today, and we already have 300 people using it.
You know, like the level of confidence that I have that the world wants this is
just so high.
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