following the well-warranted frenzy of angel list launching syndicates, famously active angels are forming their syndicates (earning carry) and helping startups raise money.  tim ferriss, who i’ve respected, read, and even hoped to work with (back when my team and i were hustling to do more faster and get @workables into techstars), was one of the first to put angel list syndicates into practice.

tim ferriss

tim ferriss

tim, known for the four hour work week / body / chef, launched the news of his syndicate with a blog post -- which also announced the startup with which he would first invest: shyp.

while reading the blog about tim’s investment, and reading tweets about brand spanking new angel investors joining in the mix, i was initially caught in the gravity of what this meant for startups, venture capital, and entrepreneurs for decades to come.

and tim's not the only one getting in on this deal.  homebrew and hunter walk -- who is also on my personal hero list -- were in on the deal and wrote about it here and certainly make a good case for the pain point shyp is targeting. 

yet, as i kept thinking back about this, i couldn’t help but think -- fuck.  isn’t shyp just a niche taskrabbit or workables?  workables, of course, being my previous (relatively failed) startup.

still love the old @workables logo

still love the old @workables logo

way back (circa 2010), my cofounder and i were attempting to build a real-time marketplace for small jobs… some of which are what the entire focus of what shyp is trying to solve.  quite a few of our jobs actually had to do with tasks like shipping.

shyp (currently beta) offers to send “shyp heros” to your door, and they’ll then take care of packing and shipping whatever you want.  not a bad idea.  something i’d use now and again -- if the price was right / if the experience was amazing. but as i play this out, i struggle to see the long-term home run... but they do make a compelling video.

so why are tim and hunter, long-time heroes of mine and successful investors, investing in this seemingly limited company?  why have i seen some of my friends jump on his syndicate bandwagon and plunk some money into shyp? wasn’t workables so much better?  or were we just a too early?  

without question the growth of services like uber -- where you get what you want immediately and thusly are willing to pay a bit more than you should -- will help services like shyp find a market.  plus, the ubiquity of mobile provides an opportunity to make this a more seamless experience for both sides of the market.

perhaps i’m still more cynical than most, having tried to form a similar -- albeit less focused -- company, but i know how hard it is.  plus, i’ve seen zaarly (to whom we later sold workables) struggle and pivot.  taskrabbit, at least operating model-wise, seems the closest to shyp.  not having any first hand knowledge, but it appears that shyp’s “heroes” are equivalent to taskrabbit’s, well, taskrabbits.  whereas workables and zaarly didn't put our own t-shirts on the people doing the tasks.

plus there’s still the problem of shipping costs.  amazon has spoiled us into thinking that shipping stuff is virtually free, even for two-day shipping.  but head on over to ups, fedex or -- heaven forbid -- the usps and try to ship something with relative urgency, and it will cost you.  not only money, but also time -- my wife recently reminding us just how much time we spend waiting.

to shyp’s credit, they no doubt have a better team than we had. seriously.  plus i like their focus (which is great getting started, but then limiting as you scale).... for workables, i think this lack of focus hurt us early on.  focusing on a vertical or geography would have helped a ton at the outset (even if we had went with the exact same site and name). 

i’m eager to see how syndicates change angel investing -- maybe even getting my feet wet -- but i’ll also be rooting for shyp.  i hope they succeed, and i’ll be interested to see how they do it… might even inspire us to dust off @workables for another go :)

Authorjonathan hegranes