The right investor, the kind who can help startups get over the inevitable “We’re Fucked It’s Over” (WFIO) moments, can turn a startup into a multi-billion dollar company. The fact is that choosing the right investors, whether it be at the seed level or at a Series B or C stage is a life-changing decision for an entrepreneur and a startup. The wrong investor match could derail a startup. “It’s like a marriage and it might even last longer.” That’s how Kleiner Perkins partner Chi-Hua Chien describes the relationship between investor and entrepreneur. And he’s not joking in the least bit. It’s a dilemma that many entrepreneurs face when it comes to signing term sheets—which angel, seed, and/or venture investor do I choose? What got me thinking about this particular subject was hearing Dave Morin chat with PandoDaily’s Sarah Lacy about Path’s road to success. Referring to the company’s reported $100 million-plus acquisition offer from Google, Morin (who in the conversation didn’t elaborate much on the offer), did highlight that he didn’t want to sell, and having his investors on board with that decision was incredibly important for the company’s future. As Lacy had reported last year, the weekend Morin was making the decision, he consulted Moskovitz, who gave him the confidence to go with his gut feeling. As for being able to make the decision to turn down the offer and continue iterating on Path, Morin credited the importance of having the right investors who shared his vision for what Path could become. Which is now a $250 million-plus company.And rumor has it that someone with the power to do so has stated that Path would be worth buying for a billion Survey any number of entrepreneurs, investors and VCs on the subject of choosing the right investors and you’ll find out that it’s actually a pretty controversial subject filled with horror stories of investment-entrepreneur matches gone bad. Here are some of the observations and advice that I put together from a number of startup founders, investors and VCs. Asking The Right Questions “What baffles me is the lack of questions that come from entrepreneurs at the table,” says Tony Conrad, who is a partner at True Ventures, and co-founder of About.me and Sphere (both companies were acquired by AOL separately). “You really need to look at the person across the table and understand what your needs are.” He explains that entrepreneurs are in as much of a buying position as investors. Conrad says that in conversations with potential investors, it’s extremely important to understand how they think about cultural DNA and how these investors, with their experience and approach to involvement, could impact the culture of the company. “Entrepreneurs don’t realize it but early investors can play a significant role in shaping a company,” he says. Bo Fishback, CEO and co-founder of mobile-focused peer-to-peer marketplace recommends asking specific questions around the nature of a VC or investor’s decision-making process within the firm. Fishback, who has raised $15 million in funding from angels like Ashton Kutcher, Paul Buchheit and Bill Lee, as well as from investors including Kleiner Perkins, and CrunchFund (*Disclosure: TechCrunch founder Michael Arrington also founded CrunchFund), says that one of the things he didn’t realize was important in the investor-startup relationship was understanding the decision-making process inside a VC firm. In particular, he advises startups to ask questions about how autonomous a partner or investor is in terms of decision-making within a firm. Specifically with Zaarly, Fishback said that they ended up working with an investor (and declined to name names) who didn’t have full control over how much could be invested in the Series A round, terms and other issues, and slowed the whole fundraising process down. “These were decisions and conversations that should have gone fast,” he explains. “Ask a lot of questions about who at the firm ultimately makes decisions.” With Kleiner Perkins he says, partner Chi-Hua Chien was able to make decisions independently, which made the investment process with the firm much easier. Fishback’s one piece of advice when it comes to choosing the right investor is not to fall in love with the a firm’s name or reputation but really focusing on whether the actual person leading the deal is the right fit. The reverse of startups asking questions is also important, Fishback adds. He felt more confident with investors who actually asked compelling questions about the startup, the market, competition, business and more. It’s not just about acting interested, but actually doing the research to come into the meeting with educated questions, he says. J.R. Johnson , serial entrepreneur and founder of recently launched social travel site Trippy agrees with Fishback’s view on investors and question-asking. Johnson has just under $2 million from Sequoia Capital, SV Angel, Rob Solomon, Rachel Zoe and others. “They need to find a balance between asking the hard questions and showing enthusiasm,” he explains. He says the old school traditional VC mentality is that companies pitch VCs and they get to choose, but some of the investors and firms getting better deals are the ones who feel and act as if there’s a two way street in the decision making. Part of showing this mentality is coming to the table with research and thoughts about where the startup is heading, challenges in the industry and thought-provoking questions, he says. In the end it’s about finding a balance between asking the hard questions and showing enthusiasm, Johnson adds. Due Diligence VCs and angels tend to do a tremendous amount of diligence on a company and founders before investing. From a financial point of view, this just make sense. But many of the VCs and founders I spoke to agreed upon one trend: not enough entrepreneurs do the same sort of diligence on investors, and can thus find themselves in dissatisfactory relationships down the line with these individuals and firms. Andreessen Horowitz general partner and entrepreneur Scott Weiss firmly believes in reference checks. Weiss was the co-founder and CEO of IronPort networks, which was acquired by Cisco in 2007 for $850 million. “Always do reference checks on the investor, especially if he or she is going to be a board member.” Chien, who has served as a company founder, early employee of several startups as well as an investor in his career, compares the choice of investor to dating someone, and potentially making a long term commitment (i.e. marriage) to them. He says entrepreneurs should evaluate how many investments an investor makes in a given year, and ask for references from 3-5 entrepreneurs who worked with the investor. And it’s important to get references from startups who have both succeeded and failed with the investor (if applicable). “Talk to as many CEOs of the companies angels or firms have invested in as you can,” warns Fishback. “Many founders take it for granted that an investor will be the right fit because they have done a lot of investments or had big wins but you have to do your due diligence.” Bringing Value It seems like a given that you’d want to choose investors that bring value to the table, but strategically it is important to understand what that value is ahead of signing any term sheets. Weiss’s advice when it comes to finding investors who could bring value stems from his days founding IronPort. “When we were first launching the business, we tried to find people that know and understand the market. Find experts in the field, perhaps the top ten individuals, and just ask for advice and thoughts about your company and your idea.” He says that if you can get them excited about the opportunity, many of these individuals could end up investing in the company. And because these investors also happen to be involved and knowledgeable in the market, they “have driven through potholes you’re about to drive through and typically have a lot of contacts and potential employees for your business.” When raising his seed round for Trippy, Johnson said that one of the main objectives when evaluating potential investors was “How can this person support the business.” With Brian Lee, a serial entrepreneur who has co-founded ShoeDazzle, LegalZoom, and The Honest Company; Johnson felt his insight from a product standpoint would be invaluable to Trippy. Johnson said that Factual CEO and founder Gil Elbaz as an investor made sense because he was one of the smartest people he knew and because Trippy is dealing with so much data, Elbaz’s experience would be helpful. And with some of the less traditional angels such as celebrity fashion stylist Rachel Zoe, and musician Jason Mraz, Johnson felt that each had a unique following of people who would trust their recommendations, and their brand would help grow the business in different directions. Zaarly’s Fishback is also of a similar mindset to Johnson. “I’m a big believer in the Ocean’s Eleven model for the seed round with lots of people putting in small amounts of money,” he says. “It’s about putting a network of people around you.” Fishback raised seed funding from Ashton Kutcher, Felicis Ventures, SV Angel, Paul Buchheit, Bill Lee, Michael Arrington, Naval Ravikant and Lightbank. In fact, Fishback says that even in the actual arrangement of the seed round, he started to see some of the benefits to having a well-connected group of angels. According to Fishback, Kutcher felt that SV Angel would be a great fit in the seed group for Zaarly, but the round was full. So Kutcher dialed back his investment to let SV Angel into the round. While having a group of well-connected angels can be a huge win for an early stage startup, Conrad advises startups to have an anchor in larger rounds. “Rounds with 20 investors where there is no leadership can be really messy,” he says. “Having an anchor in these seed rounds is very important.” Weiss also has advice to help entrepreneurs extract value from larger seed rounds. He says that from the round, put together an advisory board of the four people from the round that will be most helpful to the startup and have that board meet every month to six weeks. Chien says that he asks founders to give him actual jobs. Each week, he spends a day or an afternoon (depending on his to-dos for each company) at his portfolio companies, which include Path, Klout and Zaarly, and has a set of responsibilities for each of them. “Having that kind of hands-on support from investors in both the good and difficult times inspires confidence in startups,” he explains. The Warning Signs, WFIO And The Hard Times Weiss says there is a term in the Valley for the challenging moments startups face: “We’re Fucked, It’s Over” (a.k.a. WFIO). He says that so many startups go through WFIO, but sometimes it’s the investors that can help pull companies from these “Valleys of Despair” as he puts it. At Andreessen Horowitz, part of the mentality of hiring partners who are previous founders and CEOs of technology companies is that these individuals can help during the WFIO times as well as the peaks. He adds that it is important to have at least one investor who has experience as a founder, or in the particular market a startup is tackling, and can help calm the CEO during a storm, which will inevitably arrive during the course of a startup’s life. “Having old hands on the table that can be a calming force is very important,” he says. Chien says that in his experience as a founder, employee and investor, what separated the winners from the losers of every one of the companies that went through periods of significant challenge was whether or not the investors stuck with the company. Conrad says that founders should look for investors who have reputations amongst portfolio companies for having steady, predictable behavior. One of the warning signs he has seen both as an entrepreneur and as an investor, is that when things are going well at a company, “investor x” is awesome, but when things get weird or there is a challenge at a company, the investor is uneven emotionally, or even unsupportive. He believes that many times, these scenarios occur with younger investors. And he doesn’t mean by age—he says experience as a founder or early startup employee tends to make investors more reliable in times of crisis as well as during the good times. As for warning signs of what could be red flags for startups when it comes to investors, many times this can be a gut feeling, specific stipulations in a term sheet or even responsiveness. Many of the individuals I spoke to said a potential investor who is not responsive via email or phone during the fundraising process is likely to be the same post-raise as well. Conrad highlights blocking rights to the sale of a company as a term he dislikes in the VC and investment world. “I think it is inappropriate for us to have a blocking right on the sale of a company,” he says. He used Kevin Rose’s recent sale of mobile development lab Milk, in which True Ventures was an investor, to Google. “Kevin felt like it was the right thing to do. Would I have liked to see him to go deeper and longer. Yes. Do I think he could have? Yes. But this is his decision not ours,” he explains. However, whether you have the pick of the investment litter or are more on the “beggars can’t be choosers” side of things, it’s helpful to think through some of the advice mentioned above when deciding to whom you give that final “I do.”