Nat Turner went through an acquisition most entrepreneurs only dream about. His advertising technology company Invite Media was acquired by Google in 2010 for $81 million, a mere three years after he launched it. But while some entrepreneurs would retire on that kind of exit, Turner is itching to get back into startups after helping Google with the Invite Media transition. “After the transition is done, we’re very excited to start another company and get back on the saddle,” he says. “We’ll likely be looking to build something in an entirely new industry to make sure the first big one wasn’t a fluke.”

Turner always knew he wanted to be an entrepreneur. He started several companies before and during high school, including a reptile-breeding operation (yes, really). “There was never any question that it was what I was going to continue to do,” he says. “I could never really imagine having a real 9-5 job, it never really seemed like an option.” He went into college with several companies under his belt, and says one of the earliest startup lessons that sticks out in his mind is “you get luckier the harder you work.” “It was important to learn given that a large part of success in the business world is certainly luck, but you can position yourself to get lucky more often if you just work harder than everyone else.” He also says managing expectations was a good lesson to learn early. “You need to manage customer, partner and investor expectations correctly, for instance ‘under promise and over deliver.’”

While at Wharton’s business school Turner continued to start companies, including a food ordering website. A year later he decided he wanted to build something bigger. Along with classmates Zach Weinberg, Scott Becker and Michael Provenzano, he started Invite Media, an ad technology company that built a media buying software platform for banner ads. Weinberg and Turner got the idea for the company after working at VideoEgg (now called SAY Media). “We had noticed how screwed up the online advertising industry was in terms of technology complexity and adoption,” he says. “Starting Invite Media at first was both an attempt to address that observation but also an attempt to build a big business.”

Despite their big idea, the founders didn’t know anything about the online advertising business, specifically how decisions were made on what to buy, who made those decisions, and what technologies were used. “We used to call that the ‘dollar flow,’ whereby one of our first exercises was to try and map where each dollar spent on online advertising starts and ends, and which products touch that dollar at each step,” he says. “You’d be amazed at how many steps that can be.”  After they figured that out, they encountered technical challenges in terms of building a scalable and international real-time serving system. “After that and concurrently, we ran into challenges around building out a world-class services team and doing sales to major agencies and advertisers,” he says. “None of this we had ever done before, but we figured it out mostly.”

Invite Media launched in April 2007, and Turner says the company went through four pivots before finding their groove. They built and operated the first universal buying platform for display media, Bid Manager, and were acquired by Google in June 2010 for $81 million. Becoming a part of a global organization like Google is a challenge for any startup, and Turner says changing the startup dynamic is inevitable. “Any time a startup is acquired by a much larger company, it’s going to hurt things that startups do best like late-night creativity,” he notes. “But hopefully you gain a lot of other things, and our experience with Google has been just that.” He says they’ve gained resources, and credibility with clients and partners. “It’s very much been positive for Invite Media and our clients.”

Turner is now making angel investments in early-stage startups like Coursekit, usually with co-founder Weinberg. He says they’re very biased towards young first-time entrepreneurs with the product, design or technical ability to build something. He says the reasoning behind that is simple: it’s who they can best relate to given that they experienced many of the challenges founders will face very recently. “We also try to find entrepreneurs who are smart and scrappy enough to pick the right market at the right time, and are less focused on the specific idea they’re working on that minute, as it will always change,” he says.

For any would-be entrepreneurs contemplating starting their first business, Turner says you just have to jump in with both feet. “If you want to be an entrepreneur, stop writing business plans and talking and just start building something and get it out in the wild,” he says. For founders who are already well on their way, Turner advises learning how to listen and ask questions, and work harder than your competitors. “For whatever reason, whether the luck that you generate or sheer output, those who work harder will have better outcomes.”  And no matter what stage of a company, Turner encourages entrepreneurs to always try to advance technical and/or design skills. “Even if you’re not going to be a full-time programmer at the end of the day, every bit of technical/design skill you pick up will pay dividends in product management and being able to understand and relate to the technical folks you work with.”

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David Cohen is the founder of TechStars, one of the largest and most successful startup accelerators in the world. Though he’s now seen as the go-to guy for mentorship, it wasn’t always that way. Before his TechStars days, Cohen started a company called iContact, which he calls a “graceful failure.” He says it was that experience with iContact that taught him the importance of mentorship. He didn’t have any mentors around then, and he later met people who could have helped his company from going under. “Mentorship is the missing component for a lot of early stage companies.”

Cohen decided to become entrepreneur after getting his first job after college. “A lot of entrepreneurs go through that, they work for somebody and then they realize that they never want to do that,” he says. “I got that one job, worked there for about a year then started a company and have always been in startups since then.” He started and sold companies including Pinpoint Technologies and earFeeder.com, and built iContact in between. It was through building and subsequently folding iContact that Cohen learned valuable lessons about failure and entrepreneurship. ”Every startup that you do teaches you a lot, the ones that fail teach you the most. I learned a lot of specific lessons relating to the internet including the importance of distribution, and just how critical that is to the success of just about any internet startup,” he says. “At that time there were no app stores or open systems and really the phone carriers controlled distribution. The gatekeepers who control a market are difficult to work with.”

It was 2003 when iContact shut down, and Cohen reflected on it with a post-mortem in 2006. He says in nine years the approach to failure hasn’t changed much in the U.S. “In general, we’re really fortunate in this country that people accept failure,” he says. “I travel all over the world and talk about entrepreneurship and in many places its not tolerant.” He believes every company that fails should write a post-mortem because writing it down forces you to think about the lessons that you learned from that company, and it also could help someone else going forward. “It’s really powerful to do but not a lot of people do it.”

Cohen launched TechStars with Brad Feld, David Brown, and Jared Polis in 2006. The mentorship-driven seed stage investment program runs three-month long programs in cities like Boston, Seattle, Boulder and NYC, taking technology businesses from idea to viability through mentorship, access to investors, and funding. Each of the ten companies selected for a class receive $18,000 in funding and are offered a $100,000 convertible debt note, and graduates of the program raise an average of $1 million in outside capital. TechStars has launched now-acquired companies including BrightKite and DailyBurn, with 104 companies in the alumni network.

The program also features a network of mentors including prominent investor Fred Wilson, and Foursquare founder Dennis Crowley. Their approach to mentorship is what Cohen calls the “Socrates approach.” “The mentor does not know all, the mentor is simply there to share their own experiences and to be supportive of the company however they can be,” he says. “Big red flags go off for us when we have mentors that say this is absolutely how it is and I’m right. Instead they can say I’ve been in four experiences, it’s always turned out this way and hopefully you can learn from that and talk to other people.” He says the best mentors are happy to be told no.

TechStars made headlines recently when it was revealed that it’s harder to get into the program than to get into Harvard. They receive hundreds of applications for each spot, and founders are constantly trying to figure out what they can do to stand out. Cohen says the five things they look at for Techstars in order are, team, team, team, markets and ideas. “Team is the first three, so when we say how can a founder stand out, really how can a set of founders put together a team that has some unfair advantage or unique insight into the market they’re attacking,” he says. “Why is this team the team that can do this thing? That’s the number one thing you have to convince us of.” Beyond that he says they’re looking for teams who really understand their market.

Nine of the TechStars graduates have already had their company acquired, and many more will sell in the years to come. So what’s Cohen’s advice for navigating an acquisition? He says it’s important to have people who have been through that process on your side. He tells the story of his first company, which he sold. “We bootstrapped the company and there were just a few founders and we did really, really well with it. But I got to know the CEO of the company that acquired it over the next few years and he told us very directly, ‘You left half the money on the table.’ Otherwise, you sucked at negotiating that deal.” He said that because it was his first exit, he didn’t go find a mentor that understood those dynamics. “We did great, but we left half the money on the table.” The lesson for startups is to get someone experienced to help you navigate an acquisition. “I’ve seen Brad Feld double outcomes on phone calls for our companies at exit,” he says. “He has the ability to just understand what’s happening and how to negotiate. He’s had a wide range of experiences.” He says at Techstars they take six per cent equity, but it will probably double a company’s exit value. “Not only because of the experience and negotiating, but of the number of people the acquirer gets on their team. Mentors, mentors, mentors is the answer.”

For entrepreneurs who don’t have access to investors, bank loans or friends and family money, bootstrapping can be the only way to get an idea off the ground. Back in 1989 Bruce Poon Tip was one of those founders who had to rely on his own resources to start his company. With only an idea and his personal credit cards, Poon Tip bootstrapped his adventure travel venture G Adventures, which over 20 years later offers tours to over 100 countries. “It was difficult for us for many years at the start,” he says. “I would even go so far as to say our first ten years were hard because we had to fund such a huge growth curve and never had as much as a loan. I was very aggressive in building the business. Fortunately, I have a very high tolerance for risk, but that doesn’t work so well for the bankers.” Poon Tip knew entrepreneurship was in his blood from a young age. Most entrepreneurs say they don’t work well in traditional work settings, but not many can say they’ve been fired from McDonald’s. “I had three businesses before I turned 16,” he says. “When I tried a regular job at McDonald’s, I was fired.”

In 1989 Poon Tip went traveling and eschewed the traditional options, which were taking a coach tour, bus tour or cruise, in favor of backpacking. “When I wanted to travel back in 1989, there weren’t any travel companies like ours,” he says. “While I was travelling, I met many others who were looking for a more culturally-focused and responsible way to travel. That became the inspiration behind G Adventures.” He originally called the company Gap Adventures, because he said it was about “bridging the gap” between mainstream travel and backpacking.

Today eco-friendly and sustainable tourism is all the rage, but back when he launched the company in 1990 it was a novel concept. “We didn’t have a name for it at the time, but we knew we wanted to do the right thing,” he says. “The world later caught up to what we were doing.” Originally, the goal was to create a low-impact form of travel that appreciated the world and showed it in an authentic way. He says the coach companies and destructive tour packages represented everything his team was against. “We developed a new way for people to see and experience the world. For us, it’s always been about innovation.”

The travel industry is extremely competitive, even more so since the recession in 2008 and the European debt crisis. In addition to competition from the traditional coach, bus and cruise tour companies, he now faces competition from online build-your-own vacation sites like Expedia, and a new crop of eco-friendly and sustainable tourism companies. Poon Tip says his approach to competition is all about staying focused. “Watching what other companies do would really drag us down and take us away from driving our own innovation,” he says. “We can’t expend a lot of energy being concerned about what others are doing. We are very visible now, and your perspective is different when you’re the market leader.”

He says the company outpaces competitors in terms of customer service and satisfaction, something that has become a part of the G Adventures culture. Similar to how Tony Hsieh has started a happiness revolution in the workplace with his company Zappos, which was acquired by Amazon in 2009, Poon Tip has made culture a central part of his company. He laughs off the title of the Canadian Tony Hsieh, but admits the two share the same outlook on workplace culture. “We do share a lot of the same values towards business,” he says. “The G Adventures business model is driven by happiness, freedom and creating community. It’s a bit more complex as we operate in over 100 countries and change people’s lives every day. Our culture is our brand. I would say that we share the same philosophy on understanding the human side of business. Driving the best customer service on the planet remains our goal.”

Poon Tip says maintaining that level of customer service when running a global workforce can prove to be a challenge. “It’s about creating freedom and happiness,” he says. “Ultimately, happy and free people are motivated to deliver the best customer service.” One constant that always tied his employees together was the Gap Adventures brand. But in 2011 a lawsuit was brought forward by The Gap clothing retailer, and a court ruled that Gap Adventures had to change its name and logo when doing business in the United States. Poon Tip decided to rebrand to G Adventures in September 2011 instead of fighting the case, and the new name came into effect on October 1, 2011. He says the transition has been easier than he thought it would be. “We had everyone on board with the idea and we executed a flawless plan. Admittedly, it wasn’t a huge change, but it was significant enough for us to make the statement – to prove – that our culture is our brand; that our customers own our brand, not us,” he says. “We surveyed our travellers, team members, partners and future travellers extensively. It was exciting and the approach was innovative.”

When asked about his biggest piece of advice for entrepreneurs, Poon Tip again points to happiness and culture as keys to success, echoing the old adage of ‘do something you love and you’ll never work a day in your life.’ He also says founders must understand their motivation and define themselves in terms of the type of entrepreneur they are. “Not everyone creates for a living,” he says. “There are many entrepreneurial people who own franchises, run corner stores or even work with a more out-of-the-box type of thinking for established companies. It takes a level of focus, hard work and determination to take the ideas inside your head and present it to the world. It is a very personal process that many people don’t think about.”

His company has been around for over 20 years, and Poon Tip says he wants to continue to grow as a leader. “I’ve resolved to become more focused, since I know we cannot grow collectively unless I improve personally,” he says. “We’ve got a few tricks up our sleeves though. We might be the original and the biggest, but this old dog has a few more tricks.”

Kevin O’Connor became an entrepreneur because of two people: Steve Jobs and Bill Gates. The investor and co-founder of DoubleClick and several other companies says he always had an inventive nature, but his dream was to get his PhD and then work for Bell Labs. “I thought the only road to innovation was via a PhD,” he says. “But around this same time a couple of college drop-outs named Steve and Bill were out there changing the world with the personal computer. I knew then that a PhD wasn’t necessary – and Bell Labs ultimately went bust.” He was accepted into the PhD program, but declined to work on his own company, a software company he started in 1983.

It was while brainstorming ideas in his basement with co-founder Dwight Merriman in the mid-90′s that O’Connor stumbled upon his big Internet idea. “After narrowing in a few ideas we explored their potential.  Is there a problem and does technology solve that problem most efficiently? That’s as simple as business gets,” he says. He started reading books about advertising theory, and realized that technology could dynamically serve ads to the right user at the right time; it was no longer just a theory. “Things advertisers were dreaming of doing could be possible on the Internet.” The pair launched DoubleClick in 1995, and it became a billion-dollar company over the course of a decade. Along with CEO Kevin Ryan, now the founder of Gilt Groupe and Business Insider, O’Connor and Merriman grew the company until a private equity firm acquired the company for $1.1 billion in 2005. The company was later acquired by Google for $3.1 billion in 2007.

After being an entrepreneur for 25 years, O’Connor decided to start O’Connor Ventures so he could be on the other side of the investment table. “I love the challenge of taking on a big problem and identifying the best solution,” he says. “After 25 years of trial and error, I think I have figured out a way to create something out of nothing, creating new ideas and turning them into successful products in the market.  I wanted to help other entrepreneurs by sharing some of my processes and insights.” He says likes founders who are really passionate about what they’re doing and believe they can change the world.  He also says he prefers to invest in companies with at least one founding engineer since tech is so fundamental for the success of the company. “And finally, can the founder afford to take the risk,” he says.

O’Connor Ventures is no longer seeking investments due to O’Connor’s return to entrepreneurship. “A couple years ago, I became increasingly frustrated and disappointed with the Internet,” he says. “I could find endless amounts of information on any subject but when I had a complicated decision to make, I found myself wasting hours, or even days, compiling information I could compare.” Or he found sites offering top 10 recommendations, but discovered they were secretly getting kickbacks from the sites they were recommending. So in 2009 he launched FindtheBest.com with the goal of filtering excessive junk and presenting information in a simple, comparable way.

FindtheBest is an unbiased data-driven comparison engine with funding from Kleiner Perkins Caufield & Byers. ”While the Web is great at making seemingly infinite amounts of information accessible, the Internet can be a little overwhelming in that it doesn’t allow for straight up apples-to-apples comparisons, nor is it transparent enough to allow you to spot those hidden marketing schemes influencing the data you receive,” he says. He says he uses FindTheBest to plan family ski trips, while his eldest son is using FindTheBest to compare colleges. Scaling across many verticals has been challenging though. “I’ve been asked ‘are you trying to boil the ocean?’ but the more I looked at the challenge I realized it’s the same process whether you are making a decision about the best college for your kid or the best dog for the family.”

O’Connor has built companies in the ’80′s, ’90′s, and ’00′s. He says the main difference between building a company in 1995 and 2012 is the fact that the Internet is essential. “In 1998 we were just laying the foundations, building roads, laying the plumbing, many didn’t know what it was or how to use it.  Today I can go online while flying across the country and Obama has a blackberry.” He says back then it was hard to focus on your core competency as a startup because you also needed to build your own infrastructure. “Most companies were doing it all themselves, from creating the software to deliver their website to developing an ad serving system. Some of our biggest competitors at the start were publishers that had already built an ad serving system.” Today he says startup costs are lower and there are infinitely more resources. “When starting DoubleClick we couldn’t scale fast enough, at FindTheBest.com we can scale in a day.”

O’Connor says entrepreneurship is all about standing behind your convictions. “If you chose an innovative, entrepreneurial path, you must believe in your convictions so strongly that you would stand behind your opinions no matter who tries to discourage you,” he says. “A new way of thinking often attracts a lot of nay-sayers, you can’t let that discourage you.  Of course, there’s always a chance you’re delusional – sometimes tough to tell the difference.” He says the mark of a great entrepreneur is how many profitable products they invent – they’re inventing and innovating constantly. “Ideas that take off are often a numbers game where you need to come up with a lot of bad ideas before you come up with the great idea. You must be persistent; don’t give up.” He also says successful innovators get things done quickly because they know time isn’t on their side. “You might have a multi-million dollar idea, but if you don’t get it out there before someone else does, that idea will no longer be profitable to you.”

Despite his ability to capitalize on big trends – the personal computer, online advertising, the consumer Internet – O’Connor is hesitant to look to what’s next. “I never focus on what’s next because you never really know,” he says. “I’m incredibly focused on building the best tool for making decisions online and excited about building a truly great company.”

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Kevin O’Connor is taking your startup questions LIVE Monday, January 23rd at 2:30pm EST. Submit a question now, or view his full Q&A at sprouter.com/kevinoconnor.

MySpace co-founder Josh Berman knows how to capitalize on online trends. The entrepreneur behind one of the Web 2.0 era’s most successful companies bet on the rise of social networks, and after spending four years at MySpace and selling the company for over $500 million, he’s on to the next trend. “Similar to how I saw social networking arise with MySpace, I see similar trends happening today as shopping is becoming more and more exciting and is changing so quickly,” he says. He’s banking on the future of ecommerce, and is already seeing success with the launch of his latest venture, BeachMint. “Ecommerce and social commerce is in the first inning, there are many more innings to go,” he says. “We’re extremely bullish on the future of what we’re up to.”

He’s a serial web entrepreneur now, but Berman didn’t have online startup aspirations when he was young. “As a teenager I watched my grandfather run and start different businesses,” he says. “The bloodline is very entrepreneurial, and I always wanted to go into business for myself. We didn’t even have the Internet back then so I had no idea what that industry would be in, but I was really pretty fascinated with commerce and sales in general. So it was only a matter of time before I launched my first venture.”

Before co-founding MySpace, Berman spent time as a management consultant with Pricewaterhouse Coopers, and started online ecommerce startups including ResponseBase and Xdrive Technologies. In addition to being one of the company’s founders, Berman served as MySpace’s COO from 2003-2007, and was there during the sale to NewsCorp for $580 million in 2005. The site was reportedly the most-trafficked website in the U.S in 2006, but in recent years has struggled against competitors including Facebook and Twitter. The company was sold for $35 million to Specific Media in June 2011.

Berman says MySpace taught him how important the team is for a web startup. “It was interesting to know ‘hey, it’s not just about me, I need to have a great team to start the venture with,’ and I did that at MySpace,” he says. “It was very well-rounded. We had a technologist, a product person, someone to run the business, and someone to run the operations. So we had the basic core areas covered. We did that on purpose, and everyone got equity as we started.” He also says he realized the important of listening to customers. “You get early enough feedback, you make changes on the fly,” he says.

Now Berman is back and striking Internet gold again with his latest company. BeachMint is a social commerce company that provides members-only designer-curated shopping in verticals including jewelry, fashion and beauty. They’ve partnered with celebrities and industry experts, including Mary-Kate and Ashley Olsen and Rachel Bilson, to launch shopping sites with curated collections including JewelMint, StyleMint and ShoeMint. Members sign up for free, and after completing a style quiz are offered a monthly selection, and can either purchase it or skip that month’s offer. Launched in 2010 and rumored to be valued at $150 million, the company has raised almost $40 million in funding and now has over 100 employees.

Berman says the company is still young, and he’s surrounded himself with a phenomenal team, which includes co-founder Diego Berdakin. He says the early days are all about focus and prioritization. “You always have the question of what do you do first and when, what’s the most important feature, do you get to market or is the product not good enough, and I think it comes down to focus and prioritization, which continues to be a challenge,” he says. “You get presented with beauty deals, and international growth, and a bunch of other things, but really you have to go back to what you’re trying to achieve and you can’t possibly do everything.”

He says the company’s success has a lot to do with being at the right place at the right time. “We let our customers become our biggest advocates. We really leveraged where our users were, being on Facebook, YouTube and Twitter, and it’s an explosive experience where they’re enjoying the brand.” The company’s competitors include Kim Kardashian-backed ShoeDazzle, and Berman says several more have popped up in the last few months. “I think it’s ultimately good, we look at ourselves as a market leader,” he says. “As a whole it helps define a market. Before Gilt Groupe, not a lot of people understood what it was like to have a sample sale online. Groupon didn’t exist a couple years back and now people know what a daily deal is. We just need to remain a market leader.”

As a serial entrepreneur, Berman says starting multiple companies allows you to build upon what you’ve learned. “Being fortunate enough to be part of something that was extremely extraordinary, which MySpace was, you learn a lot very quickly,” he says. “I had a fortunate opportunity to work with executives at leading companies because of that, and I got to maintain my relationships and credibility as a businessperson, so I think that’s helped me blossom as an executive and it’s a lot easier to pick up the phone and talk to someone.”

Before starting BeachMint Berman ran Slingshot Labs, a startup incubator dedicated to building and developing new web ventures for NewsCorp. He says a lot of young entrepreneurs he sees have a lot of ideas, but it all comes down to focus. “They want to do multiple things. It’s really all in, and you have to be so good at focusing on your vision. I think that’s a key piece of the pie – some people are dealing with multiple things and I think it’s really difficult to be able to pull that off.” He says it’s key for first-time entrepreneurs to pick a great team. “Have teammates, don’t just keep all the equity,” he says. “Some people are more technologically savvy, some are more strategic, some are more marketing, so your team is really your partners. You’re working 12+ hours with your teammates, and that’s critical to have the right team.” Once the product is launched, it’s all about paying attention to your customers. “They’re going to be your advocates, your early adopters, and if you have any question on what you’re building and why you just have to keep asking them because that input truly is the best way to execute a successful product launch.”

Berman is currently focused on expanding BeachMint internationally, with Canada being the first market outside the U.S.  ”It feels great to fill the international demand,” he says. “There are a lot of international markets and a lot of international opportunities.” Berman’s banking on them, and on the success of social commerce – and he’s been right about trends before.

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We’ve been a team of four people at Sprouter for almost two years (not counting a few awesome interns who have helped along the way), so we’re excited to announce a new addition to the team today! Jon Spenceley starts today as Sprouter’s new Community Manager, and our fifth team member. Jon comes to us from Freshbooks, where he spent almost three years on the customer support team. He was also responsible for support on the Freshbooks Twitter account, for many posts on the company blog, and for organizing company parties and customer meetups. He has led panels at South by Southwest Interactive and several other events across North America.

Our newest hire Jon Spenceley

Jon will be running our Sprout Up events, working with our panel of experts to expand the Q&A in 2012, and helping our community of users, evangelists and entrepreneurs to leverage our service.

Jon is passionate about customer service, running events, and creating happy workplaces (bonus for us). He’s excited to dive into the world of startups, and bring his own flair to the Sprouter team! Say hello to him on Twitter at @jonspenceley, find him on Sprouter at sprouter.com/jonspenceley, and email him at jon@sprouter.com.

Welcome to the Sprouter team Jon!

Most entrepreneurs want to grow up to be the next Mark Zuckerberg. Kevin Ryan wanted to grow up to be a CEO. The former CEO of DoubleClick says he had aspirations of senior management, rather than a dream of Ramen noodles and basement coding. “I knew I wanted to run a company, I wasn’t necessarily thinking I would start from scratch,” he says. “If you’re in the car industry its almost impossible to start up a car company. You’re better off joining a car company and moving your way up.”

In 1995 he was working for a media company and launched a website as part of what they were doing. “I realized there was ample opportunity in the internet space to launch things on your own and just huge amounts of opportunities,” he says. He decided to launch his own company, and while researching the market came across DoubleClick, a similar company that was six months ahead of him. “I realized the technology they developed was pretty interesting, so I was better off just joining it. They only had about 20 people, they were 1% of the way there,” he says. He joined the company as CEO in 1996, and remained in that position until a private equity firm acquired the company for $1.1 billion (the company was later acquired by Google for $3.1 billion in 2007).

Despite DoubleClick’s acquisition, Ryan wasn’t content to retire, and quickly got into the entrepreneurial game. He started Alleycorp, a network of affiliated companies run by Ryan and former DoubleClick CTO Dwight Merriman. “After that experience for 9 years, I still thought there were big opportunities so I started Gilt and the other companies as well,” he says. “Now we have well over 1000 people and very successful businesses.” The AlleyCorp businesses include news site Business Insider and luxury flash sales site Gilt Groupe, though when it began Ryan didn’t have any ideas in mind. “Each year we started one or two companies for about three years. If you have an idea and you become convinced of it you have to start it right then,” he says. “If you wait a year someone else will have done it. You never know when those ideas are going to hit. For example I started Business Insider and Gilt in the same month. It just so happened I thought these were both really good ideas.”

Ryan spends most of his time on Gilt, while remaining chairman at Business Insider and board member of 10Gen. The companies are both now so large that they are run independently. Up until each company had about 100 employees the two companies shared services, financial people and information technology. “As each company moved out to their own space and left the room, they had to be completely independent,” he says. Since its launch in 2007, Gilt has expanded from a flash sales site for women to include offerings for men, kids and home. The company raised a $138 million round of funding in May 2011, and was expected to hit $500 million in sales in 2011. In an interview with The New York Times, Ryan said the company would consider an initial public offering in 2012.

After years of working with Merriman, both as a colleague and a co-founder, Ryan says finding key people to work with is more important than titles. “Whether or not you’re going to have someone called a co-founder, you’re going to need key people. Even if you say I’m the only founder, who’s your first employee? That person doesn’t have a title but they’re essentially a founder.” He says it’s also about complementary skills. “You want to find someone who you get along well with, but ideally has complimentary skills,” he says. “I think there can be a risk if you’re both MBAs or both engineers or both sales. It would be too biased in one direction.”

Ryan believes that 80% of business success is having the right people. He says he interviews potential candidates every day, and his companies hire two people a day during certain periods. He says delegation is key, because if he was to make every decision things would slow down. “I need great people and that’s what makes the business work,” he says. “There are 12 people under me on the business side who are now CEOs. One of the tests I give to people is if they have a company of a 150 people, do you think 10 years from now that they are so good that can could actually do this in a company 30 times larger. Most people would say no.”

Gilt recently announced plans to launch internationally in over 90 countries. 45% of the company’s revenues come from people who live outside the United States, even though the company doesn’t take international credit cards and doesn’t ship outside the U.S. “They either have a friend who has their apartment in Boston, or Chicago or they send it to their sister to bring it over,” he says. He says Canada is the number one market outside the U.S., and they’re seeing hundreds of orders every day since launching there.  And as for international competition, such as BeyondtheRack? “There are currently flash sales players in almost every country in the world, there aren’t very many that have a high end assortment and range that we do,” he says. “I think it’ll be a good offering.”

Wayne Gretzky famously said that a good hockey player plays where the puck is, while a great player skates plays where the puck is going to be. Yammer founder David Sacks says it’s the same with startups. The former PayPal COO says you don’t want to create the 20th version of something that already exists, you have to be innovative and stay ahead of the proverbial puck. “Startups always have to do that, you always have to be ahead of the curve,” he says.

Sacks has worked in tech startups for over 10 years, but he didn’t always see himself as an entrepreneur. “I didn’t completely know because I went to law school. By the time I was in law school and spent the summer in a law firm, it was enough to convince me I didn’t wanna do law. So I moved into business and once I did that I realized I wanted to look at the startup scene, be part of something smaller that was building some rapidly.”

He worked in finance for a brief time after law school, and then ended up joining PayPal in 1999, and eventually became Chief Operating Officer until the company’s acquisition by eBay. “Peter Thiel convinced me to quit my job and join Paypal,” he says. “We talked about it for a couple months, but I got excited about it when the idea shifted from beaming moneys on Palm pilots to emailing money. I thought it was a good idea, it was a great team of people to work with.” After his stint at PayPal he started a movie production company in L.A. and produced the movie Thank You For Smoking.

It was his first foray into starting an online company that led to the idea for Yammer. He created Geni.com, a genealogy website, and had created a Twitter-like chat application to use internally. But soon that internal tool because a viable business idea. “We built Yammer originally as a tool inside of Geni and we were using it ourselves so we decided to spin it off,” he says. He launched it at the TechCrunch 50 conference and then decided to spin it out into its own company. “I generally base my views on products and companies based on my experience as a user,” he says. “I really loved Yammer because I loved it as a user.” He believed there was a market for it based on the fact his team liked the product, but back when they launched in 2008, people didn’t feel there was a market. “That’s been something we’ve had to prove over the last few years,” he says. “We’ve invented this category of enterprise social networking, that didn’t exist before. When we first launched it, people were dubious about the idea that social networking would work for the enterprise and be valuable for the enterprise. Now I think the idea has almost been seen as inevitable.” He says most people would now agree that every company should have its own internal social network, but back then it wasn’t obvious.

Yammer launched at TechCrunch 50 and won that event. Sacks says that’s how they got their first 50,000 users, and from there it was a combination of word-of-mouth, press and the inherent virality of the product. “We let anybody sign up with their company email address and then you can invite your co-workers, so its viral within companies,” he says. “That’s really helped Yammer spread faster. We’ve also worked on making a great product so there’s a lot of word of mouth.” It took the company about 18 months to get to a million users, nine months to get to two million users, and it just grew from there. “What you want to see is a rate of growth that is increasing,” he says. “If growth is linear or flat, you just won’t be able to go fast to prevent your idea from being over taken by competitors. The increasing rate of growth is extremely important.” But he says ultimately you need to build a great product. “With those wave of applications built on Facebook all they focused on was being viral and then Facebook finally turned off a lot of these viral channels and people stopped using the apps because they weren’t valuable,” he says. “First and for most you have to build a product that is valuable. Start thinking about how do you make the product self-distributing in some way. Does it have a built-in mechanism where users will want to invite other users so it is viral?

Yammer has raised $57 million in total funding, including a $17 million round of series D funding in September 2011. But even though getting customers on board with the concept of enterprise social networking was difficult, getting investors on board wasn’t too difficult. “Getting the money was not the hard part and I still don’t think its the hard part of a startup,” he says. “The hardest thing right is now is getting engineering talent on board. There’s a lot more money out there than software developers.” Sacks moved Yammer from L.A., where he started the company, to Silicon Valley in 2009, and says he thinks it’s important for entrepreneurs to be in a larger startup community in order to find success. “I think its a mistake if you’re in some small town somewhere,” he says. “You need an ecosystem of not just the founders but of the talent, software developers, investors, press contacts, etc. Part of the advantage of being a eco system like Silicon Valley is that there are a bunch of successful companies so you get a better idea of what it takes to create a world class company.” He says a change of location helped Yammer scale. “When we got to Silicon Valley we started thinking a lot bigger and growing a lot faster.”

If Sacks had to give aspiring entrepreneurs one piece of advice, it would be to make sure an idea is solid before starting a company. “You should really think about idea before you start a company,” he says. “I see a lot of entrepreneurs just starting a company because they want to start a company without really having the best idea or thought through why it is a good fit for them pursuing the idea.”

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Rarely is a startup an overnight success. Even if a company seems to come out of nowhere and sell months later, there were usually years of work behind the scenes. That’s the case for Pandora founder Tim Westergren. The founder of the popular personalized online radio service launched the company in 2005 after working on the initial idea since 1999. The company filed an IPO in June 2011, 11 years after he started working on it, and after facing several “pull-the-plug kind of decisions.”

Westergren started his first company in 1999, and has always worked independently. “I’m not sure I would have used the word ‘entrepreneur’ back when, but in hindsight, yes,” he says. “I’ve definitely always enjoyed being my own boss and have always been less content to work toward someone else’s direction.” Westergren also says he’s always had a pretty healthy appetite for risk and “a commensurate level of naiveté to enable the risk taking.” After graduating from Stanford University, he worked in the music industry for many years as a record producer, musician and composer. It was while working as a film composer in Los Angeles that Westergren came up with the idea to map musical tastes. “My job required me to work with film directors to figure out their musical taste,” he says. “Over time I found myself developing a methodology to map tastes against musical attributes. This sparked the idea to codify this taxonomy and, by marrying it to mathematics, create a recommendation technology.”

It was 1999 when Westergren launched his company Savage Beast Technologies with friends Will Glaser and Jon Kraft. “Will and Jon were terrific partners to get this company off the ground,” he says. “I absolutely recommend partners — I’d actually go even further and say you shouldn’t do it without them.” His idea to map musical tastes became the Music Genome Project, which is the foundation of what Pandora is today. The Music Genome Project is covered by a patent, but Westergren says that in general entrepreneurs spend too much time and money worrying about IP protection. “Very few businesses live or die based on good patents,” he says. “Being overly focused on that can divert vital resources, as well as cut off opportunities because of worries over secrecy.”

In 2000 he pitched the idea for a music recommendation engine based on the project, and raised over $1 million in VC funding. But his timing was awful. “We wound up launching right when the first technology bubble burst,” he says. Even though they had the idea, Westergren says the biggest challenge to actually launching Pandora was financing. “It was very hard to raise investment money for the first few years due to the economic climate in the technology industry,” he says. The business model went through several iterations, and Westergren pitched over 350 investors before raising $8 million in financing from Walden Venture Capital. It was 2005, five years after first trying to launch the project, that Pandora finally launched online. “Eventually, over many years, and with the incredible contribution of many talented people, we managed to create Pandora,” he says. The service uses the Music Genome Project to create radio stations based on one song, artist or genre chosen by a user. It automatically populates related music into an entire station based on that initial choice, using the taxonomy of the Music Genome Project. Westergren says it was pretty clear shortly after the Pandora launched that they had something special. “The growth in listeners, which was entirely by word of mouth, was pretty extraordinary right out of the gate,” he says.

By 2008 the Pandora app became one of the most popular applications in Apple’s app store, and it’s now one of the top five most popular apps across all smartphone platforms. Today Pandora is the leader in personalized Internet radio, and accounts for 60% of all Internet radio listening in the U.S. The company may have 100 million users as of July 2011, but Westergren, who now serves as the company’s Chief Strategy Officer, says it isn’t all about the numbers. “What brings me the greatest sense of satisfaction and accomplishment is watching our team grow and flourish,” he says. “It’s an amazing feeling to look out at 450 faces at an all-hands meeting and see the pride and excitement they all have in the company.” Another big milestone for the company was filing its initial public offering in June 2011, raising $234.9 million in its debut on the New York Stock Exchange.

Despite Pandora’s popularity since launch, there have been big obstacles along the way. In 2008 Westergren said Pandora was facing a “pull-the-plug kind of decision” due to wrestling with what he calls a broken royalty system that punishes internet radio. “We pay a disproportionate share of our revenue to rights holders, far more than any other form of radio,” he says. “It’s an ongoing battle for us that we hope will eventually find a more rational solution.” He says 2007-2009 was a particularly rough period with the Copyright Tribunal that governs the industry. “Throughout the uncertain times around the royalty battle, I think that our employees maintained a steadfast belief in the product and in the support we were getting from our listeners. Ultimately, it was the grassroots support of millions of listeners that pulled us through. It was quite an amazing thing to experience.”

The company has struggled with its business model over the years, and currently makes money through advertising and premium subscriptions. Another roadblock was when Pandora had to pull the plug on its use in international markets due to licensing constraints. It’s a sore point for former international users, and Westergren says what’s next for him is taking Pandora global. He says his advice for aspiring entrepreneurs contemplating starting a company is “do it” – something Westergren did over 11 years ago, and he hasn’t looked back since. ”If you trust and value your people, it won’t matter how big you get, your company will remain a great place to work,” he says. “We spend a lot of time at Pandora these days thinking about this.”

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Victoria Ransom has lived in a favela in Brazil, spent six weeks in a remote village in the Amazon, and launched several companies. The avid traveller and serial entrepreneur says building a startup and adventure travel have a lot in common. Both involve expecting the unexpected. “Be open-minded and creative and don’t give up just because you hit a road block,” she says. “When the road washes out in front of you, sometimes you forge a new path through the jungle.” They also both involve adapting at a moment’s notice. “Nature and the market always throw unexpected curveballs such as typhoons and housing market crises. Adapt to your situation to make it easier on yourself.” And finally both involve taking calculated risks. “Base jumping is a calculated risk,” she says. “So is pivoting your business from one model to another.”

It was lifelong curiosity that led her to travel in the first place. “My parents instilled in me a deep drive that’s kept me moving pretty rapidly throughout my life. Ambition and curiosity have been inherent in that drive,” she says. “Growing up, I didn’t necessarily have a plan for my future; I just wanted to lead an interesting life.” In college Ransom wanted to explore over the world and immerse herself in different cultures, which resulted in her global travels.

After college Ransom became an investment banking analyst at Morgan Stanley, but felt like something was missing during her time there. She was passionate about travel and thought there had to be a way to allow others to experience and derive as much pleasure from travel as she did. “I decided to leave the banking world and start a company called Access Travel,” she says. Along with co-founder Alain Chuard, Ransom was able to travel the world and build adventures for other people. “When we made that leap, we both thought, ‘Well, what’s the worst that can happen if it fails?’”

Their next spark of business inspiration came while looking for a way to market Access Travel with promotions on Facebook. “While Alain and I are both tech savvy, we had incredible difficulty finding an effective solution,” she says. “So we decided to design a tool for ourselves and hired some developers to build it.” What was supposed to be a side project quickly turned into a viable business idea when they began to get phone calls from other companies, including Zappos and Kayak, that wanted to use the tool they saw on their page. They launched Wildfire as a separate company in 2008.

In the early days of the company Ransom says the biggest challenge was finding the right team members. “With any big idea, you have to realize you yourself are not scalable, and will never be enough to make the business succeed,” she says. “When you’re a very early stage company, it is easy to be grateful for anyone who is willing to work for you, but it’s critical not to compromise on quality or culture. The first people you hire will help set the pace, the culture, and the vision of the company, so have a very high bar.” She advises entrepreneurs to consider hiring people who have a large network. “At Wildfire we benefited from the fact that our initial sales hires had large networks of contacts in sales; this was critical to our early hiring efforts.”

Since launching in 2008 Wildfire has evolved into a tool to create interactive promotions on multiple social media platforms, not just Facebook. Companies can create branded contests, sweepstakes, coupons and other promotions; manage pages; and see campaign analytics. The company counts some of the world’s biggest brands among their tens of thousands of customers, including Pepsi, Disney and Toyota. The company is a two-time winner of the fbFund, a seed fund run by Facebook, Accel Partners and Founders Fund, and has raised $4 million in funding.

Ransom says winning the fbFund was essential to their success. “The fbFund provided us with the capital we needed to get our product to launch and to reach profitability,” she says. “But even more important than providing us with capital, it gave us the opportunity to build strong ties with Facebook, receive mentorship from some of the best entrepreneurs in Silicon Valley and meet with many of the top VCs and investment firms.”

In three years the Wildfire team has grown from two to almost 250 employees. “I am proud of the incredible team that we have built at Wildfire and the fact that we were recently named one of the top ten places to work in the Bay Area,” she says. “I’m also proud of the huge impact we’ve had for our clients – we hear from clients that thanks to Wildfire they’ve experienced some of their best sales days ever, or grown their revenues by double digits, or increased their customer databases by hundreds or percentage points.”

She’s worked with the same co-founder for multiple companies, and Ransom says you have to choose your partner extremely carefully. “Before you can even imagine having an entire workforce, you have to select the right founding partner,” she says. “I have heard too many stories of people founding viable businesses that then implode because of co-founder issues.” She advises founders to pick someone that can complement you, not your friend from business school who has the same skills as you. “Make very clear from the start who is going to do what – if you both want to be the ‘face’ of the business, this will likely be difficult – and ensure you have the same vision for the company culture.” She says having a co-founder with a different skill set that complements you means you can share the responsibility of leading a company forward in a balanced way. “You will have different views but this is important in deciding on the best foot forward for the company.”

Aside from picking a co-founder carefully, Ransom says to be critical of your idea. “I see a lot of people who are in love with the idea of entrepreneurship and in an effort to get started they don’t always critically examine their idea,” she says. “Entrepreneurship is extremely competitive. If you have a good idea, something that has a big market opportunity and significant revenue potential, it’s guaranteed many others will have the same idea. You need to believe you have some special advantage that will help you succeed.” That could be a first mover advantage, or knowing your target industry really well and having great contacts in it, or having access to great intellectual property. But often other founders with the same idea can validate what you’re working on. “If you look into the market and don’t see anyone who’s doing your idea already, ask yourself why? Is it because you’re the first person to think of the idea or is it because the market opportunity isn’t really there?”

Ransom and Chuard are now focused on hiring, with 50 positions currently open. “We’re also continuing to hire rapidly and aggressively scale our business,” she says. They’re expanding Wildfire internationally, and will be opening offices soon in Singapore and Paris. While she still has an innate curiosity, these days Ransom’s international travels are less about adventure and more about business success.

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Want to ask Victoria about her journey building Wildfire? Ask her your startup questions LIVE Thursday, December 15th at 4pm EST. Submit a question now, or view her full Q&A at sprouter.com/victoria_ransom.