Yeah, I've heard about this recently. It looks pretty decent. There are a lot of legit investors on there ... most of the guys in this view are awesome:

http://angel.co/vc?field=&order_by=followers

Man that sucked -- I typed up a pretty big response to this but then closed the tab and when I un-closed it it had lost the reply

Anyway, I've gotta head out now but I'll re-reply later. Other than that I think I'm caught up... Sweet! Let me know if I missed anything besides this one and the recruiting thing I will circle back on.

Thanks lgas for replying.


If I may ask, how did Ebay and Milo come up with the valuation of 75m for Milo? Was it based off current web traffic + potential growth?

What type of goals was Milo trying to achieve besides raising money? Getting this feature by x date? This many users by x date? Revenues by x date? etc


Just trying to get an idea how both Milo and Ebay thought they'd be worth that much and what Milo will eventually grow and profit into.

How realistic is it for someone with very little tech experience to find a job with a startup, assuming little to no income requirements?

I am picturing a position that would be more involved in the business development side of things, and am more than willing to trade present income for the chance to be the part of something interesting and challenging every day, with the possibility of being a part of something huge.

If realistic, is there a good place to find out about these kinds of jobs? Would love to stay in Colorado, but I am getting the feeling that you basically need to pack your bags and head to Palo Alto...

Do a lot of networking and be honest about who you are and what you can do. If you don't have a track record that shows you can do what you say, then figure out a way to do something, anything, that will convince them otherwise.

I got an internship with a 10-person company up in NY a couple summers ago by just sending the two founders an email explaining who I was, what I had done, what I liked about their company, and how I thought I could help. There was no position available, but I flew up their on my own dime and met with them for a day, hit it off, and had a great 12 weeks there.

Don't limit yourself to sales/bd. There are a lot of startups that need serious help with operations, finance, etc. A lot of them hire part-time CFOs to manage the books, and just leave everything dealing with operations to chance until they get about 12-15 people and significant enough traction so that they actually have time to focus on something not product related.

The more you can bring to the table the better.

Boulder is probably 2b after SV (1) and NYC (2a) for hot startups right now. Great community, great investor base, all good stuff.

Sorry if this was answered already, what is your role with Milo now and in the future?

On a more personal note, what's your plan now that you've made it?

Thanks again for all the info, Q&A and sharing!!

Can someone with zero technical skills found a startup?

I have an idea for a website or app that I've always wanted to see created, I just have no idea how to go about doing this. Does it ever work for someone without technical skills to pay someone to develop their idea?

Not wanting to hijack what has truly been an outstanding discussion by lgas, but it has already been mentioned a few times it's pretty difficult without a technical founder if it's a technical startup.

You can get cheap labour through sites like www.vworker.com, but you should seriously consider networking big time to find someone to help you. Lots of developers have their own ideas or would love to be a part of something but have no business sense or cash to get going - hopefully you can supply both of those to get it going.

It will be cheaper both short term and long to just learn how to do a minimum viable product yourself.

Yes, this is great advice in general. The only two points I might take exception with are:

#5 - We certainly used some proven interviewing techniques (e.g. creating an engineering challenge to screen candidates) but we also went off the beaten path and tried to find new ways to ensure that candidates were a good fit. I am not sure how much of our recruiting process I can discuss but I'll look into it and hopefully post some more details about this.

#7 - We have had more success with head hunters here in the valley than I've ever had elsewhere, but in general I think the cream of the crop (especially when it comes to engineers) is much more reachable via networking and personal referrals than via head hunters. Generally speaking if you're a top notch engineer you probably have never had to go through a head hunter... there's always a line of people waiting to snap you up the second you are thinking about leaving wherever you are.

The logo came first, then the name, then the dog. After we got the dog we considered flipping the logo so they matched but we never bothered. Also, I have to say, Milo the actual dog is an awesome dog. He has an amazing disposition and he's really smart and fun to play with. I think he also has a great affect on morale around the office.

It's funny, I've occasionally joked around pretending to be mad if someone refer's to John Hamilton as just "John" but we're a pretty laid back group here and we don't take that stuff to seriously. Also I think it's more a matter of senority than "importance" or anything really... If I had been hire #23 and he had been #24 it would've worked out the same -- likewise had he been hired first it would've gone the other way even if I was still in a more senior role than him or something like that.

As far as the confidence part goes, I've actually always had a lot of confidence and probably dated a bit above my level on average, but I think the biggest affect right now is that since the acquisition I've sort of been in an "on top of the world" mindset and that feeling probably leaks through in a lot of my interactions with women (or in people general) and that's just something people and especially women are probably drawn to. Of course one nice aspect of it is that even if that is sort of a temporary affect the increased success rate now has increased my general confidence level even more, so I think it will be a more permanent improvement.

Both of my parents have always been very supportive. Over the years I've always been pretty open with friends and family about what I'm doing and what my goals are and what my expected outcomes are, etc. I also have always been pretty optimistic so I'm sure that everyone was pulling for me but also taking sort of a "we'll believe it when we see it" stance.

Specifically with my parents I was pretty communicative about how things were going for the whole time but as things got busier and busier I communicated less and less, and then by the time it became clear that the deal was going to happen I started holding off on communicating anything intentionally so that by the time it happened it was a pretty big surprise.

They were both pretty shocked and then elated for me.

Again, can't go into a lot of details, but I think this was a fairly typical acquisition in that as things got really serious near the end of the process eBay put a number on the table and there were some negotiations and then a final number was agreed to.

I can't really speak to exactly how eBay arrived at the initial number or what factors went into the negotiations from their point of view since I wasn't involved in that side of things, but generally there are a couple of reasons that big companies will acquire startups: to get technology, to get patents or other IP, to get talent, to get revenues, to get marketshare and/or to enter a new market, or because there are synergies that could lead to more efficiencies working together than separately.

There may be some others but I think those are the main ones. In our case I'd like to think it was a little bit of everything but probably the top 3 would be talent, entering a new market and technology if I had to guess.

In general I think the going price for talent acquisitions in the valley is about $1m/head so since we only had about 25 people but sold for $75m it was clearly at least not just a pure talent acquisition (acq-hire) play.

We were (and still are) basically pretty metrics driven, so we have a lot of numbers that we plot on graphs such as daily unique visitors, bounce rate, repeat visit rate, conversion rates, product coverage numbers, # of merchants covered, # of products covered, % of population covered, all broken out in all sorts of different ways and we are basically always trying to grow (or shrink, depending on the stat) all of the numbers but at any given time we decide what the 1-5 most important metrics to be focusing on are and really just attack those. What is in our cross-hairs usually changes almost weekly.

As for what we'll grow into... well, we'll just have to wait and see

Thanks so much for taking the time to re-type all of that! Were you involved in the hiring of all the current employees?
What percentage of your workforce are tech workers?
Did you lose anyone in the sale?
Roughly how well did the average employee make out (mid/low/high 5/6/7 figs if that isn't too specific)?

What has been your favorite part of being part of Milo?

I read a great article on Flipboard (probably from TechCrunch) about how the standard practice is for a board to replace the CEO as a start up becomes more successful (Steve Jobs was the famous example). Was this ever a concern of Jack's?

Can I ask if you three co-founders controlled a majority share of the company?

Do you wish you had taken more equity and less pay? What did you feel the chance of Milo's success was when you decided to come on board?

mmbt0ne's response pretty much nails it. I would add that the "little to no income requirements" part definitely helps a bit but I would try to use this as an advantage to help land an ideal job with a great startup and make sure you're not using it to let someone mediocre take advantage of you. There are a lot of people out there that will either try to outright take advantage or just have very low likelihood of success and you don't want to spend a lot of time earning very little money to have nothing to show for it in the end. Make sure that if you're going to do this you're at least working with a great team that you can learn a lot from.

I don't have any personal experience with Colorado but it is definitely possible to do startups outside of the valley, and as mmbt0ne's response indicates, there are some specific areas that are good alternatives like NYC. If you can find a significant startup presence online from that area it'll probably be fine. That being said I think the valley is still the best place to go if you want to squeeze every last ounce of edge out of the location.

Our organization moved over to report to a VP at eBay pretty much entirely intact, so all of our titles got adjusted to fit within eBay's structure but from a practical perspective nothing has changed.

I split my time between serving as sort of a a lead architect (the good kind, not the bad kind ) for eBay Local and doing actual development on skunk works projects.

Well, as I mentioned early on in the thread I'm incented to stay at eBay for at least a year (and I'm starting to lean towards thinking it's worth staying longer) and I want to stick around for a while anyway just to sort of see things through.

I do have a startup idea in the travel space that I'd like to try when the time is right but it's not time sensitive so I'll leave that on the back burner for now and maybe work on the prototype or some market testing in my free time if I feel motivated to do that...

Now that I have more free time I'm getting back my social life and dating more and am going to try to start playing more poker both live and online.

Other than that I plan to travel more in sort of three distinct areas: 1. go back to the MD/DC/VA/PA area to visit friends/family more often, 2. go to vegas frequently (once a month?) and 3. see the world (I was planning to go to Egypt for a while but I think I might hold off on that, the next couple spots on my list are probably Costa Rica and Thailand).

I also would like to learn to snowboard and just for the purpose of reinforcing stereotypes maybe try to get good at golf.

MangoPort's reply is basically right. It's certainly possible but the more technical the product/service/site/idea is the more you need a technical co-founder.

This applies to any area though, not just specifically web technologies -- if you had an idea to do a cooking startup wouldn't you want a chef or at least someone with experience in the restaurant industry as a co-founder? Sure you could get by without it, but isn't it going to make it a lot easier if the person you're counting on to make all of the "technical" decisions' interest is aligned closely with yours?

I get what you are saying here but I think it depends a lot on the nature of the product.

If the product is "an ebook" and the strategy is "affiliate marketing through *********" then yeah you can probably go at it alone and learn as you go, etc.

If, on the other hand, the product is Milo, or Quora, or Hunch, or even a facebook game or whatever, you're probably going to be better off getting an expert involved in some capacity, whether it's a co-founder or not.

Obviously my inclination is to try to go for the co-founder role but if you don't want to do that you're still better off with having an expert involved early instead of trying to learn everything on your own. Especially if you're not already somewhat technically inclined because then you have no way to even judge how much you will need to learn and therefore no way to know whether going at it alone is even a reasonable decision or not.

I was involved directly in the vast majority. I would say there were maybe 3 engineers that I wasn't involved too much with and I more or less just tried to stay out of the way when we were hiring the 3 or so business people. The other 18 or 19 I was directly involved in some way in the process (interviewing, assessing engineering challenge, selling them, etc).

About 19 out of 24 or 25 (I guess I really should figure out an exact # ).

We had one person who was accepted into y-combinator almost immediately after the sale closed so he left to pursue his own startup. We have one other person who is on sabbatical. That's it.

Since the acquisition we have also hired on someone who was an intern for us last summer into a full time role and we are evaluating some eBay people as possible internal transfers.

I'm reluctant to get into too much detail here for a couple of (hopefully obvious) reasons, but I will say that in a deal like ours my expectation would be that there would be a few people that are high 5's, a majority of people in low-mid 6's and a couple of people in the 7's and our result was not really too out of line with that.

This is a tough one. Really the whole experience has been rewarding on so many levels that it's hard to narrow it down too much, but I'll take a stab at some of the highlights:

1. It's extremely rewarding to have been able to have built a team as great as we did. I like every single person we hired as a person and have made many friendships here that I am sure I will maintain for the rest of my life. It's also great to just be surrounded by a team of such high quality people all of the time -- they are all extremely smart, friendly and fun. I can't imagine a better way to spend my day-to-day time.

2. I've learned sooo much about so many topics. I feel like I have a much much better grasp on how to make the right kind of technical decisions in a startup but I've also gotten an amazing look into the business side of things and I know understand a lot better what matters and what doesn't from the business perspective. I feel like in general the skills I've learned which can be applied to my next startup are almost more valuable than the money I made doing this one.

3. Building a consumer facing application that actually gets used by over a million people a month is pretty rewarding. I have built some large scale systems (e.g. the software that replaced weblogs.com when VeriSign acquired them, the servicing and tax systems at Freddie Mac, etc) but I had never worked on a consumer facing product that got any real traction before. It's even better that what the product does is help people save on time, money and frustration, especially in this economy.

It think it's impossible for any CEO in a VC backed startup to not at least consider this possibility and try to prepare for it, but I doubt that Jack was ever especially worried. I think one of the main reasons for this is that often
the founders do not have a strong business background but rather just a product oriented one or maybe they just had a great idea, etc. But the bottom line is they are just not long-term CEO material. I think despite his young age, Jack is definitely CEO material and probably had much less risk of being replaced than most.

On top of that the VC firm that lead our series A, True Ventures, has a reputation as being extremely entrepreneur-friendly, and that was definitely our experience. These guys are the best and I highly recommend working with them if you ever get the chance. I don't think they are the replace-the-CEO type in general and I personally didn't really worry about it at all in our case. If we had gone with someone like Sequoia I think it would've been a much bigger concern. Also I think in our case if we had worked with a VC that tried to replace the CEO they probably would've faced a revolt from the rest of the company.

Not sure if I am allowed to discuss this. Will put it on my list of things to ask about.

When I first decided to come on board I was pretty bullish on the idea... But even if you think a startup has a massive chance of success you're talking realistically maybe 20% chance of a non-total-failure outcome, with the chance of massive success infinitesimally small and maybe thinking a 10% chance of having an outcome anywhere close to as good as we did or better.

Basically over time I only got more and more certain that we would experience some level of success. At any given point I wished that I had more equity than I did -- and as I think I mentioned I even took at pretty significant salary reduction (to about ~50% of my initial salary) as soon as I could in order to increase my equity.

Obviously in retrospect if I had been able to do it at the time I would've not only taken zero salary and all equity but also supplied as much of the initial angel/seed/series A as I could myself -- of course hindsight is always 20/20 but even without the ability to predict the future I definitely ratcheted up my equity as much as I could.

If you're reading this thread you may find this amusing:

http://www.youtube.com/watch?v=3J9Kh...&feature=email

Obviously this is a joke but I think there's an important lesson lurking here which is that ultimately every startup situation is different and it's important to not get too caught up in any of the conventional wisdom or startup fads and instead sit down and think through your situation and figure out what's important and what's not and what will work and what won't.

Great great thread, very inspiring stuff.

I have a question about your equity stake in Milo:

-Did you have to give up a lot of equity in every round of investing?
-Was there any pressure to dilute your stake?
-If not, then how did you manage to not dilute your stake from first joining the company to eventual buy-out?
-Did you hire your own lawyer to look over the documents to make sure that you didn't get screwed?

There is always dilution in every subsequent round of investment but we managed to structure the series of deals so that it was never too bad. If you're on a good trajectory you generally don't have to worry about this too much. Your percentage becomes smaller but the idea is that it's now a percentage of a much larger pie (both in terms of the fact that the business now has increased operating capital directly increasing it's value but also that the EV of the whole company increases due to having the capital as resource to use to grow the company even further).

I did not have my lawyer look over anything and I got lucky that it turned out ok but I would definitely advise other's to do it if they are in a similar situation. There were definitely a couple of points in time where I said to myself something along the lines of "I'm glad it turns out I wasn't getting screwed on x or y or z" and it could've easily gone differently.

One other thought that occurred to me about the advice I've been giving in this thread:

One of the things that I noticed about a lot of the advice we got from advisors throughout my time a Milo is that the advice you get from someone successful is almost always (and rightfully so) tied to their direct experiences.

This means that if you were successful at Microsoft in the early days the advice you give is going to be advice that would be good for Microsoft in the early days. If your successes were with B2C companies your advice is probably going to be better for B2C companies than B2B, etc. If your success was at a service company it's probably going to be better for other service companies than for product companies, and so on.

I guess the simple take-away from all of this is that whenever you're getting advice from someone you should take it with a grain of salt and specifically you should consider the source and what experiences they have that have lead them to the beliefs they hold and to be giving you the advice they are giving you. The closer their situation is to yours the more valuable and relevant the advice is and vice-versa. This of course applies equally to any advice I may have dispensed in this thread.

This is not to say that advice from someone who had success in a completely different field at a different time in a different market won't be spot on for you, just that you should try to make that determination yourself and not blindly trust any advice anyone gives is good for you. There were definitely some advice that people gave us that we had to ignore because it just didn't apply to our situation because there were one or more differences in fundamental factors.

Here are a couple of threads on a failed attempt at entreprenuership that may be of interest to some of you:

http://www.reddit.com/r/IAmA/comment...oney_and_time/

and the hacker news thread on the same post:
http://news.ycombinator.com/item?id=2183615

-Was the equity dilution evenly distributed among the founders at every round of investing?
-As to the whole lawyer situation, did your heart skip a beat when you saw what could have happened to you after watching the Social Network?
-Poker question: What kind of stakes were you playing before the buy-out and what kind of stakes are you planning on trying out live/online now that you are flush with cash?

Congratulations on your success!

As a CS student I'm looking for advice on what kind of stuff you looked for in candidates beyond the normal requirements. I see on your team page the past companies you come from and even on companies where it is notoriously hard to get into such as google or goldman, on their openings page the requirements are usually just a bachelors in CS and a selection or programming languages. As someone who isn't going to the most prestigious university I'm hoping that a strong portfolio is more highly regarded than just having gone to Stanford. Or maybe networking plays a stronger role?

Basically I want to know what I can be doing in my free time to make myself as strong a candidate as possible. The usual advice is contribute to open source projects... what's the typical extras you would see at a grad level person you would consider interviewing and hiring?

Yep, proportionally distributed (evenly distributed percentage-wise).

More like breathing a sigh of relief that it didn't, but yeah.

Prior to Milo I was playing mostly live $10/$25 NL in Atlantic City. Occasionally just above ($25/$50) or below ($5/$10).

My old roommates and I also hosted a crazy $1/$2 home game in Ashburn, VA for a couple of years but it played more like a $2/$5 or so, sometimes higher

This was just prior to the startup that I sunk a lot of my own cash into and I actually encountered some other expenses (e.g. taxes) that I basically spent my entire bankroll on. As a result almost the whole time I was at Milo I didn't have the bankroll to play at stakes that were meaningful to me. (Even though, in theory, the stakes that were meaningful to me should've adjusted downward, it's hard to play micros after playing deep $10/$25 games all the time)

I tried to play online at micro/small stakes and spin up an online bankroll but due to a number of factors (stakes being so low even though it was all I could afford, never having enough time to play so trying to force action when I could, tilt, exhaustion/burnout, etc) was never successful with that.

As a result I am guessing I'm one of very few people who can say I'm a big winner at $25/$50 live and a loser at $25NL online... well actually now that I think about it, that may not be such a small pool

Anyway, I haven't really had time to jump into a good mid/high limit game live yet. I am planning to play some mid stakes NL at either Lucky Chances or Bay 101 sometime soon.

I did destroy the $1/$3 game at the Hard Rock in Vegas for about $1,100 in 2.5 hrs two weekends ago. That was a lot of fun and really got my poker juices flowing again. Sorry if any of the HVAC convention attendees or regs from that game that were at my table are reading this thread

Online recently I've been playing a little HUNL in the $100NL - $400NL range to get used to things. I haven't played enough to have a meaningful sample but so far I've busted my account every time I've deposited... but I've already had a couple of epic battles (e.g. against staceyanne79) and I'm confident that I'll be a threat soon enough. I'll probably keep depositing and playing at these limits as time allows and try to to build a bankroll and move up from there as my bankroll allows.

I just looked myself up and maybe I need to tone down my aggression a bit:



Once I have the time to get back into it more I'll probably subscribe to deuces cracked or something and buy some coaching.