First Pitch

Going Back to Where It All Began - Greenville, SC

I’m heading back to Greenville, SC on Wednesday to hang at The Iron Yard for a few days. The plan is for me to “mentor” the current batch of startups in the accelerator. I have a lot of unique experiences to share with the startups so hopefully I can share some insight and first-hand knowledge with everyone. Make no mistake, I am no startup expert or one of these sought after gurus. I just want to help in some capacity and lighten the load of stress one can feel in an accelerator.

I openly admit, I love Greenville (as evidenced by my Facebook cover photo). A smile comes to my face when I think back on the four months I lived there. It is a strange thing, though. Most people don’t move out of their home, leave their wife and kids behind and live in another state for nearly four months. These things, of course, were the worst part of pursuing this passion. So while I smile when I think about the best experiences I had in Greenville, I can’t help but to feel some guilt for leaving my family.

There is also some guilt about not having broken through with our startup yet as well. I won’t go into all the ups and downs since returning from the Iron Yard, you probably read those posts already. But I will say you can’t put the toothpaste back in the tube. Once you commit to a decision like leaving the family and starting a business it changes everything.

People say “well at least you gave it a shot and won’t live the rest of your life regretting it if you hadn’t given it a try.” I wouldn’t trade my experience in Greenville (and my love for it) for anything. HOWEVER, the ramifications of a taking a dip into the startup pool are irreversible and feeling guilty for burning your savings, leaving your wife and kids behind; and putting your spouse into an impossible position (support the dream or put a fork in it), may be worse than regretting not doing it in the first place.

Don’t get me wrong. There are so many amazing things that have come out of all this. Too many positives to list; I am just pointing out that the regretters of the world don’t know what they aren’t missing. And, we haven’t failed with our startup, we just haven’t made it to 1 yet. I suspect this will change in early May and if you know me at all, you know I will tell you if we made it to 1 or not and I will be brutally honest in my report. 

So, off to Greenville. Might drive past the old apartment at North Slope, may even go in to Publix - won’t buy anything - just want to walk through the isles reminiscing. Well, maybe not, that actually sounds kind of dumb. Why would I do that when I can visit Barley’s, Chicora Alley and maybe 2-3 other favorite places; walk Falls Park and might even bike the Swamp Rabbit Trail. But the one thing I want to do most is kick back in that white leather office chair in my old seat at [the new] Iron Yard throwing back some cold ones with my great friends and fellow Iron-Yarders. 

The Valley

Not talking about Silicon Valley. I’m talking about the valley between the peaks.

Things are getting tough in startup land. We finished The Iron Yard in late September, launched a prototype (we used to call it a beta, but let’s be honest), learned a lot and felt like we finally found the sweet spot.

The next milestone was to actually get the product to catch up to the business development. See, we have beta clients (some high profile) waiting to use our product. I suppose this is a good problem to have but I imagine the shine wears off after waiting around too long.

Here we are in March and about a week or so from pushing the update that will finally get the clients on our platform. This is THE critical moment in the life of Locally. This is when we find out if we are a contender or a pretender. Either way, it’s been about as hard this last month or so than is has been the entire journey to date.

Money running low (business money that is, personal accounts have long since been drained), tension in the household increasing daily, sense of industry is about shot, role confusion (I work for free while my wife brings home the bacon), personal torment for both my wife and I - the mental battle over to support or not to support this endeavor, to give up or not give up on this dream, become the startup killer or remain the startup supporter? It’s all madness, quite honestly. Pretty sure I am in limited company when it comes to dealing with all this stuff.

One thing I know to be fact. Startups need capital to move fast. IF you have some, you are golden, if you need to raise some, you are gonna get suckered into the “trap” real quick.

The “trap” is the toil between spending time working on raising money (which takes a lot of time especially if you have to establish investor connections on your own), and deciding to commit to just cranking out code and shipping product. You quickly realize that you can’t do squat without some money. Then while you are struggling to get meetings with investors you get pissed and decide you are going to build out more features and ship some updates. Then you realize this is moving fast enough because you don’t have the required resources….you get the idea.

The “trap” is also getting sucked into all the blogs, articles and startup “How-to’s” which are all garbage. These don’t apply to the average startup (and if you are the founder of an average startup, you know what I am talking about). I could write a book on all the traps you know why? We have fallen into what feels like every one of them.

I will wrap up with this. People ask me all the time if it was worth it to quit my job, leave my family behind for the summer, ask my wife to support me and significantly put a hurtin on the family (I was gonna say “family budget” here but really, this has been beating down on the family unit).  Not sure I have the answer yet but I certainly have learned some lessons about what is important in life. I’m not the best at seeing this all the time but I do know. All we need to do is ship the next update and then we are golden…

I’m Just Not That Crazy About Boats, That’s All

“Gee whiz Caffey you’re in the Navy for crying out loud.”

Been watching A Few Good Men tonight and this line was perfect for some thoughts I had about startup life.

Ups and downs are part of startup life. We all know this. But something every startup founder should understand before getting into the startup life is that you’re enlisting in the Navy. Sure you may get sea sick but it comes with the territory. You can’t circumvent this reality. If you join the Navy, you will spend time on the boat regardless of your vertigo.

We need to prepare ourselves before singing up for the Navy. Is this really the life we want for ourselves and our families? Are we prepared for the massive lifestyle adjustment that is about to happen? Do we understand that it is a four year enlistment? Are we ready to get in that foxhole or “stand on that wall” with our comrades?

Others have enlisted with the expectation that they will miss their family for extended periods of time, live a meager lifestyle, take risks most people cannot fathom and be there to hold up their end of the deal as all enlisted personnel took an oath to do. If you do start a startup and your co-founder(s) do not share the same understanding that you are joining the Navy, the ship you are on is likely to sink before reaching port.

You have joined the Navy and you will ride in boats even if you aren’t that crazy about boats. If this scares you, don’t join the Navy.

Moment of Confidence

I recently posted a 60 second year in review for 2012. I decided to spare you the long details of the ups and downs we experienced this year. To get to my point, we learned so much it is hard to share in a blog post. So instead I am going to jump to right now, today and discuss my moment of confidence.

I am the CEO of the startup Locally. My biz partner Luke is our developer and CTO. We are finally right where we think we need to be in our startup lifecycle. No paychecks, no funding (yet), a closed beta v1 with no revenue and a financial well that is quickly running dry. So why the hell would I say we are right where we need to be?

We’ve lived a lifetime, or at least one career cycle, in the last 6 months. It took every minute of these 6 months to refine, refactor and redevelop a product, a team and a company. But having done that we have positioned ourselves really well. Don’t get me wrong, we have work to do and lots of it, but this is a moment of confidence, not a moment to analyze.

Locally is now positioned to be a platform. Marketing for merchants, vendors and event planners, discovery of amazing local experiences for consumers. A great combination with a solid value proposition. Merchants, et al. directly engage their local market in real-time by sharing location, information and deals/offers - with the press of a button. Consumers simply open their mobile app and see which experiences, events and offers are available in their city or neighborhood. We describe it more simply as Foursquare for things that are happening right now. 

We will raise the capital required to build this out from our current beta product into the number one local discovery platform. As one investor said to us, “you just need to build it out.” We agree. 

Advisors, colleagues and fellow entrepreneurs all helped to shape us in 2012. We expect incredible growth in 2013.

60 Second 2012 Year In Review

Startup idea carried over from 2011.

Developed product/vision and began prototyping in early 2012.

Felt strongly about startup, decided to go “all-in.” 

Quit my job in May.

Applied for and was accepted into the Iron Yard accelerator in Greenville, SC.

Left my wife and two boys from June 7 until Sept 18 (saw them 3x for total of 8 days during this time).

Pivoted with about 5 weeks left before our Demo Day on Sept. 13.

Pitched at Iron Yard Demo Day Sept. 13. (then went to BMW Performance School to zip around in M3’s and 6 series)

Took the next month to adjust to living at home again. Luke, my business partner and developer, went back to Boston. We currently work remotely from one another.

In October we started to discuss raising capital and have been fortunate enough to secure initial interest.

Also in October we launched our closed beta, enrolled our first handful of customers. We capped enrollment at around 10 for initial testing.

We rebranded our food truck app, TruckyLove, to become Locally, the easiest way to discover amazing local experiences. Now open for all sorts of local vendors, businesses and venues.

Began discussions with high profile organizations in Phildelphia to sign up for Locally; meetings ongoing.

Currently, raising capital (today is December 26th).

Acknowledgments (Important people that have helped me - and Luke - along the way):

• My wife - my kids, and all of my family/friends/support network
• Charlie Crystle
• Kyle Sollenberger
• Dave Weaver
• Trini Amador
• Peter Barth, the Iron Yard, Iron Yard teams, and the Iron Yard Mentors.
• Keith Messick
• Arnold Waldstein
• Chris DiFonzo
• Eric Katherman
• Bob Moul
• Mark Spangler
• Startup Lancaster members
• Many, many others as well!

Locally

Good Morning,

While you were sleeping, TruckyLove has been transformed, mostly just our brand name. We received feedback about our software that indicated to us that we were leaving the door shut for other awesome, locals who may want to use our platform.

In response we discussed our findings with event planners, business owners and other vendors to gauge interest in using our software. The response was favorable! With this in mind we wanted to create a brand that was open