Entrepreneurs
Always Start as CEO
(and Delivery Boy)
When you have 1,000's of customers, lots of revenue, and great stories to tell to the press, the entrepreneur life looks great.
But what about when running the company is not great?
This is the first in a therapeutic blog post series for me and other startup entrepreneurs to know for certain that we’re not crazy.
(This post first appeared at http://helpflow.net/blog/entrepreneur-ceo-delivery-boy/)
I’m building HelpFlow and it’s at the stage where every day is a grind.
I’m having the time of my life, but have to do things that some people would consider crazy amounts of work for little (current) return.
I listen to a ton of startup and business podcasts, and notice a trend with all successful companies.
All successful companies start the same way- with a GRIND!
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Here’s the first of many examples that I’d love to compile with your help.
Jason Calacanis, CEO and Delivery Boy
Jason hosts the best startup podcast out right now. He started Webblogs, Inc. in 2003 and sold it in 2005 to AOL for $25 to $30 million (source: Wikipedia).
He’s done a lot since then, including angel investing in a ton of startups and hosting the largest startup conference in the world.
But before these wins, his career looked lame to the average onlooker.
1996 — CEO, Founder, and Delivery Boy
Passionate about the startup scene in New York, Jason started a newsletter called Silicon Alley Reporter.
- It didn’t start as a 300-page magazine with conferences in New York, Los Angeles, and San Francisco. It started as a 16-page newsletter that he photocopied himself at a local print shop.
- He budgetted $1,000 for the first issue based on the cost per page. But he didn’t realize you had to pay for each side of the page, so the cost ended up being $2,000 funded on his credit card.
- He didn’t have any money to send the newsletter to companies in town, so he pushed a cart around New York with newsletters and delivered them himself.
Not quite the successful startup CEO with a golden future all lined up.
Lesson Learned- If You Believe In It, Do It Yourself
There’s things in your own business that you probably aren’t doing because you just don’t feel like you’re ready.
If you don’t start doing something today, then you’ll still have nothing tomorrow.
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You can achieve the end result you’re looking for without the the trappings of a polished, sexy startup.
Jason photocopied the first newsletters of Silicon Alley Reporter himself and delivered them door to door on a cart, but it eventually turned into a 300-page magazine, conferences around the country, and a $25 million offer to sell.
A photocopied newsletter and pushing a cart door to door led to a $25M offer
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For now, just focus on getting it done.
Applying These Lessons Myself
I got the first 3 customers for HelpFlow in 10 days by picking up the phone and calling people that knew me that I knew would get value from it. The relationships gave me the opportunity to pitch them, but it didn’t get me the sale.
This was my version of Jason Calacanis pushing a cart around New York in 1996. It wasn’t a cool launch, but it worked.
The blog post about how I got these customers went viral and sent a ton of visitors to the site. Since we’re a website chat service, I ended up manning the system with constant chats from 845am PST to 11pm PST.
My incredibly patient and supportive wife laughed when she came home at 5pm and I was in the same spot as when she left in the morning. She immediatly said “let’s do our date night tomorrow honey, keep this going!”.
We know this is all part of the journey.
Are You Crazy Too?
Let’s compile a list of inspiring stories like this. What’s something you’re currently doing in your startup that isn’t sexy, but is part of the grind to get where you need to go?
