I've exchanged PMs with several people that have expressed an interest in me doing an ask me thread about my experiences.

I am the 2nd of 3 co-founders of Milo.com which was sold to eBay for about $75m on 12/2/2010. eBay's corporate communication policy prohibits me from posting anonymously when discussing anything about eBay, so -- my name is John Evans (the 2nd person listed on this page: http://milo.com/team).

Everything in this thread (or that I post on this site in general) should be considered to be my opinion or views only and does not represent the views of my employer or anyone else.

I'll try to answer anything I can about any and all topics but I'll probably have to be intentionally vague on some of the numbers and/or about details my personal life.

I have some time right now and will have some more time later tonight but I apologize in advance if my posting is somewhat erratic especially over the weekend (I'm going to the superbowl) but I've been meaning to post this for a while now and it never feels like I have time so I figured it was better to just post and get the thread going then to put it off forever.

I would love to hear about the phase between idea and actually starting to act on it. What were your first couple of steps? What gave you the confidence to actually put time/money behind it?

Should be a very cool thread! Are you going to continue to be a part of milo.com or are you moving on to other stuff?

In the beginning the specific idea was actually quite different. We basically set out to do what Red Laser (which was also acquired by eBay...) did -- an app for smartphones that would let you scan barcodes and get reviews and price comparison data on products in the store. At the time when we started out smart phones were not as ubiquitous and we ended up feeling like we would not be able to to get enough traction so we "pivoted" (to use today's buzzword from the startup world) and tried some other things. We actually went in quite a few different directions before finally settling on the specific local shopping idea.

As for the confidence part of the equation, Jack, the original founder wanted to pursue the specific idea but when trying to sell me on getting involved he also talked a lot about the bigger picture opportunity in the market. Specifically the state of affairs at that time was that all of the big comparison shopping engines had been sold off during or after the original dot com boom and they were now cash cows generating tons of money for the acquires. The founders had all cashed out and since the companies were generating piles of cash no one had any incentive to innovate.

I guess it was the combination of the larger market opportunity and the fact that commerce is one of the few markets you can do a startup in and not have to wonder how you are going to monetize it that attracted me to the idea. On top of that Jack is ridiculously smart, he comes from a successful family (his father is the founder/CEO of comScore) and was in the process of finishing his undergrad from Wharton where it was obvious he had gotten quite a good business education. All of these combined with the fact that I was in the process of trying to raise funding for a much less ambitious startup of my own at the time basically made me decide that my time/energy/money would be better spent working on this.

In my particular case there were also two big factors that helped a lot: 1. Jack had some initial seed money and was able to pay me a pretty reasonable (though drastically reduced) salary so that I didn't have to worry quite as much about money (I later took about a 50% further pay cut in order to increase my equity stake when I realized our chances of success were much higher than the average startup) and 2. I was running my own successful consulting company prior to this and I knew that if everything went horribly wrong I could return to that and be making a nice income again in no time.

I'm going to stay here for the time being. I'm an entrepreneur at heart and I already have an idea that I would very like to pursue for my next venture but it's not time sensitive and I am incented financially to stay here for at least a year.

Also, in a way, I don't really feel like I have closure yet.

We had a lot of aggressive goals at Milo and a big part of the reason we took the eBay offer is because we felt like it was a good fit and that they had the resources to allow us to go after some of the more ambitious things we wanted to do.

It remains to be seen how that's going to work out but for now I'm optimistic that I will get to see us meet a lot of those goals over the next couple of years.

first off thank you for doing this thread and congratulations for your success.

I was curious as to the nature of having secured the seed money that you originally had. What kind of track record did Jack have in order to secure this seed money and, if possible, how did he obtain the contact? Nothing specific,I mean was it someone from school, family? That's obviously a big step to make.

Would it have been possible to launch this type of a business with everyone working day jobs and no additional funding? That's what I am doing now but I have no justification for someone to invest in me. I have been building my business for 11 months (still working the day job) now and feel that I am on my way to becoming a business that would be attractive to investors.

Heading home now, will be back on in 30-45 minutes.

Tell us about how the original founder went from idea to seed to bringing you in. Thanks!

Was starting a business always a goal for you/did you always have the entrepreneurial drive?

Where did the idea originate from? I've always felt I would like starting my own company and running it/developping it but I have no idea what kind of business/product I could provide, any feedback about this?

Thank you.

Congrats on your success.

Excited to gain some insight into a normally secretive process.

Can you give rough numbers in terms of seed dollars and the steps you guys took to fund the start up. You mentioned Jack had some seed money and good financial connections. How difficult was it to find investors?

No problem, and thank you.

I believe the very first money he got was ~ $10k from winning the Wharton Venture award in 2007. He then raised a little more early seed money from friends and family as well as professors from Wharton. That is what paid my initial salary and got us through the first couple of months and to the point where we moved out to Palo Alto.

Once we were in the valley he reached out to Keith Rabois who is a well respected and well known angel investor to get feedback on the idea and direction we were headed in and that ended up turning into an angel round from Keith's firm Youniversity Ventures.

We still had the lion's share of the seed money left at this point and weren't looking for investors yet but after meeting Keith's other partners (Kevin Hartz and Javed Karim) we knew we wanted to work with them and we'd be better off taking the money to get them involved.

In terms of track record, Jack had done a few small businesses in high school and college which probably helped at least a little when it came to raising the seed money but I think that he would've been able to do it either way based on a combination of raw intelligence (which is obvious to anyone that interacts with him for any length of time) and an ability to easily demonstrate a deep understanding of the market and how to execute on ideas.

It definitely would be possible but it would have been a lot more challenging and really I think one of the things we did well early on was to recognize that there are tons of challenges and hurdles you have to get through as a startup and the more you can eliminate early on the better of you are.

It took us probably a year to get from the point where I got involved to the point where we were executing on the right idea. If we did this while working other jobs that year might've been 3 or 4 and by the time we sold Google was aggressively entering the market and there were numerous startup competitors popping up -- who knows if what would've happened but I'm sure that it would've reduced our chances of reaching the same level of success.

As another similar example of eliminating hurdles, we could've also stayed on the east coast where we both had a bigger network of both business and tech people and tried to make a go of it there, but the venture environment is different on the east coast (and especially in the DC area where there's a lot more government/defense work) and really silicon valley is where tech startups thrive, so as painful as it was for us to pack up and leave our friends and families behind, I think that was one of the best decisions we made early.

If I was in your position I would take one of two routes --

1. Go for more of a boot-strappable business -- something where you can get something simple up and start generating (even a tiny amount of) revenue immediately. Then grow it until it's generating enough revenue to quit and pursue it full time.

2. Focus on building up a team that can really execute amazingly well on the idea, then start trying to raise at least an angel investment purely on the strength of the team while you're still employed. Use the angel investment to let some or all of the people quit working and focus full time. Once the team is working on the idea full time, use the combination of the team and the prototype to raise a series A.

Obviously it depends on exactly what your idea is and so on, but something like at least one of those options should apply to whatever your situation is. If you would like to PM me details I might be able to give more tailored advice.

I don't know that many details from before I joined but I think basically what happened was that he knew he wanted to something and while he was in school he was studying various markets and analyzing opportunities and so on, and at some point he identified the general market opportunity that I described above (the comparison shopping space being ripe for disruption).

I think he was intrigued by that notion combined with the fact that playing in the shopping space (especially as a lead-gen play) means that you really don't have to worry too much about the monetization piece which makes your life a lot easier. From there he would go to his Wharton professors or other advisors with various ideas and they would always tear them apart and send him on his way. Eventually he got to the mobile barcode scanning idea and suddenly they weren't tearing it apart any more.

From there he knew that he needed a hardcore tech person. He is pretty technical and in fact did some coding on Milo but he knew there was a difference between being able to get by and actually having the experience and background to really crush it.

I had worked for his father's company when it was still a tiny startup and had helped them solve a couple of their major early technical challenges so when they were brainstorming who to get involved my name came up and they were able to track me down. It probably took three months of meeting and talking once or a week or so before he won me over to the idea that the opportunity he was onto was a much bigger and more achievable one than what I was pursuing (a play in the credit fraud prevention space).

I've always been pretty entrepreneurial... which goes hand in hand with being a risk taker and/or trying to understand and control risk, which is probably how I ended up being a poker player too.

I wrote a post here describing my pre-Milo startup path (Milo is #7 on the list):

In between the startups I worked at a couple of big companies like Discovery Channel (in their online division), VeriSign and Freddie Mac.

Well, there are at least two routes you can go with:

You can start more of a boutique or lifestyle company, which is essentially what my consulting company was. If you go this route and succeed you will make more money than you would working for someone else but you're unlikely to ever make a really huge pile of money. On the other hand the risk is lower.

You also get to be your own boss along the way regardless of whether you succeed or not or to what degree. Of course this is a double edged sword because you get all the good parts (want to sleep in one day... fine, do it) but all the bad parts (you're the one that everyone is mad at when something goes wrong, both clients and employees, you're the one that has to figure out how to cover payroll when your biggest client is late on a payment, etc.)

If you're going this route it's not so much about finding an idea but finding a skill/talent that either you have, or, probably better, can recruit a bunch of people who have that given skill/talent. In my case it was programming and I had a good network of programmers that respected me that I could recruit.

If you want to go this route I highly suggest you read "The E-Myth Revisited" before you get to deep into it. The general thesis of the book is that if you have a technical skill and you want to quit your job to start your own company exploiting that skill you need to realize that your success will depend at least as much on your ability to do all the things that aren't that technical skill (eg. accounting, HR, marketing, sales) as it will on your ability to do the technical skill.

The second route is the angel/VC funded startup route. Here it's more about the idea but even then most companies ideas change at least a few times before they succeed. E.g. YouTube started as a dating site.

It's more important that you identify something like what I've described above where there's an opportunity in a market that can be exploited rather than figuring out the exact idea to exploit the opportunity. Then you put together a good team to execute on the opportunity and if you can get to that point you can almost pick any reasonable specific idea to start with because you'll probably end up changing it anyway along the way and the investors know/expect this as well.

(That said, if you can really nail the idea out of the gate, then even better).

I actually don't know the initial seed numbers but my guess is somewhere right around or just under $100k or so. Then I think the rest as described here is at least in the right ballpark: a bit under a mil in the angel round and about $4m in the subsequent series A.

We actually had very little problem raising money at any point. The series A we did was at one of the worst times to try to be raising money and we actually had 3 (I think) term sheets on the table and were trying to decide which one to go with when we were approached by True Ventures and they worked hard to impress us (and definitely succeeded) so we ended up choosing them in the 11th hour.

I attribute this primarily to the combination of the team (at any given point)'s ability to really execute well and Jack's ability to communicate that to investors. Of course some of the other factors (e.g. the ones that interested Jack initially and that he used to get me interested (market opportunity, ease of monetization, etc)) probably helped too.

It's probably easier in general for a Wharton educated son-of-a-successful-startup-CEO to raise money than it is for the average person but it's definitely more about putting together a team that can execute and being able to prove/demonstrate/communicate that to investors.

If you can do that it's not that hard to get the introductions you need. For example, Y-Combinator is a great way for smart founders with a reasonably good idea to get hooked into the valley financing scene. Once you're hooked in, if your idea is reasonable it just comes down to convincing investors that you and your team can execute and if you can, that shouldn't be too hard.

Oh, and now with Yuri Milner's offer to give $150k to all current and future yc companies, it's a good way to get some initial seed funding too