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<ul class="summary-list"><li><keyword id="10657693" type="UNKNOWN" weightage="60" keywordseo="manny-medina">Manny Medina</keyword> is the CEO of Outreach, an AI-based sales engagement platform. </li><li>He's learned that sacrifices will have to be made, even to parts of your identity, to get ahead of this problem.</li><li>Medina says using <keyword id="2544886" type="ORGANIZATION" weightage="60" keywordseo="Imposter-Syndrome">imposter syndrome</keyword> as a positive motivator and building a strong support network has helped him to be more ambitious and assertive as CEO. </li></ul><p>Last summer, I was <a href="https://www.facebook.com/permalink.php?id=972169476154160&amp;story_fbid=29529147247462826282">interviewed</a> by Elias Torres, the cofounder of Drift, about our experiences as Hispanic entrepreneurs in the United States. Afterward, as I chatted with attendees who were thinking of starting companies, I was struck and saddened by the amount of negative self-talk I heard.</p><p>Many of these talented young people had great ideas, but seemed to have convinced themselves they weren't cut out to be founders.</p><p><em>"I wouldn't feel comfortable walking into a room of VCs."</em></p><p><em>"I have never done this before. They would never trust someone like me."</em></p><p><em>"Who am I to start a company?"</em></p><p>I recount this experience not to be critical, but to say that I get it. I've been there. In fact, I still am some days.</p><h2><strong>As <keyword id="10657692" type="UNKNOWN" weightage="60" keywordseo="immigrant-founders">immigrant founders</keyword>, we all share some form of imposter syndrome</strong></h2><p>I've felt it ever since I left Ecuador to come to college in the US at age 20, and at every step in my journey as cofounder of Outreach. Even though I'm now CEO of a company that's valued at more than $1 billion, is listed on the <a href="https://www.forbes.com/cloud100/#1409d2055f94">Forbes Cloud 100</a>, and employs more than 600 people, I still sometimes worry whether a guy with an accent - who worked in shrimp farms most summers as a kid, and whose grandfather was a Communist organizer - is the right person to take forward the company I love.</p><p>But here's the good news. While I don't think these thoughts will ever go away completely, I've learned to control them. In fact, I've learned to let them motivate me.</p><p>Imposter syndrome is defined as <a href="http://www.hbsp.harvard.edu/hbsp/hbr/articles/article.jsp?articleID=R0509F&amp;ml_action=get-article&amp;ml_subscriber=trueber=true">a collection of feelings of inadequacy that persist despite demonstrable success</a>. It can happen to anyone, but is particularly common among women, minorities, immigrants - people who may not fit the common norms in a given community.</p><p>The current political situation in the United States exacerbates this phenomenon. Over and over, I hear the narrative that immigrants are bad for our economy and are stealing jobs that should go to Americans. Former President Trump has repeatedly demonized immigrants from Mexico and Central America as rapists and criminals and "invaders." In fact, last year the  Trump Administration put a temporary <a href="https://www.wsj.com/articles/trump-order-would-temporarily-suspend-new-h-1b-other-visas-11592853371">ban</a> on the H1-B visa program, which is how Outreach has hired several of our most talented, unique, and irreplaceable employees, particularly data scientists and other highly technical people. </p><p>This problem also extends far beyond official Washington policy. I sometimes feel that kind of resentment from people I meet in daily life, even in progressive places like the Bay Area and Seattle, Outreach's hometown.</p><p>What can other <keyword id="6422290" type="UNKNOWN" weightage="60" keywordseo="immigrant">immigrant</keyword> founders - or anyone, for that matter - do to overcome imposter syndrome? Here are a handful of lessons I've learned along the way.</p><h2><strong>1. Turn it into a positive motivator</strong></h2><p>Like most thoughts, you can't just destroy imposter syndrome, but you can control it with healthy habits and discipline.</p><p>Don't hate or judge these thoughts too much - they can even be useful. While they may be misplaced, I think they are related to the paranoia and passion and ambition that many successful people share, and those can all be powerful motivators. They can help you check yourself to make sure you're not drinking your own Kool-Aid. The trick is to never let your thoughts become debilitating. If you find yourself sitting around finding ways to justify why you're a horrible founder, it's time to adjust your mindset.</p><p>Meditation can help. I started meditating three years ago, and it's given me a mechanism to calm the negative voices in my head. It doesn't silence them, but it lets me observe my own moods and triggers. Am I sad? Am I discouraged? Why? What's triggering those thoughts? Are negative thoughts sapping my energy? Do I need to go for a walk to change my train of thought? Simply becoming aware of your thoughts without judging them is half the battle.</p><p><em><strong>Read more:</strong> <a href="https://www.businessinsider.com/future-of-coworking-spaces-freelancers-entrepreneurs-self-employed-after-coronavirus-2020-6">What the future of coworking might look like for the self-employed as they seek out ways to network, collaborate, and set up shop</a></em></p><h2><strong>2. Give yourself some extra credit</strong></h2><p>Chances are, you've had to overcome multiple challenges because of your immigrant or minority or gender status. For example, English is my second language, so I actually have to translate everything from Spanish on the fly. When I do math in my head, I do it in Spanish. That means it takes a few microseconds longer for me to answer a question or do a calculation. That's okay. Rather than beat yourself up, consider being proud of your determination to overcome challenges. It's all about perspective.</p><h2><strong>3. Accept that you'll make sacrifices</strong></h2><p>Zoom is one of the most successful new companies of the past few years, but its founder, Eric Yuan, has said that he had to work hard to <a href="https://nextbn.ggvc.com/podcast/s1-ep-15-eric-yuan-of-zoom-from-immigrant-to-top-ceo/">overcome</a> his accent. In a <a href="https://nextbn.ggvc.com/podcast/s1-ep-15-eric-yuan-of-zoom-from-immigrant-to-top-ceo/">recent interview</a>, he said, "I do think the language barrier is a factor, seriously. I was born in Shandong province in China, and when I came here I even did not speak the language." </p><p>If you have an accent, know that some people will judge or have preconceived ideas about you because of it. It isn't fair, but it is sometimes true.</p><p>I've also paid the price for my accent. For example, after we pitched one venture capital firm, the partner declined to invest because I "wasn't <keyword id="6358815" type="UNKNOWN" weightage="60" keywordseo="tech">tech</keyword>nical enough," even though I have a masters degree in computer science and Outreach is a technical company at its very core. We've been focused on machine learning advancements since our early days, and 40% of our revenues are invested into engineering. I'm convinced that I just didn't fit into this person's idea of what a tech entrepreneur should be. Did he pass on us because I didn't code the product myself, or because to him I sounded like his gardener?</p><p>Some of the sacrifices you will make might take you by surprise. I'm reminded of this every time someone says my name. My name is not Manny - it's Manuel. But early in my career, one boss had a hard time remembering my name and decided, "I'll just call you Manny." I love the guy, and I'm sure he didn't mean it to be hurtful. Since then, I've learned to live with it, but I didn't like it at all at the time. </p><p>I'm not suggesting you put up with all the slights or wrongs you face. I sometimes wonder why I never pushed back to reclaim my given name. But I've learned it's important to pick your battles, and accept the fact that you may lose some en route to achieving more important dreams. </p><p><strong><em>Read more: </em></strong><a href="https://www.businessinsider.com/how-to-optimize-linkedin-profile-resume-recruiters-keywords-advanced-search-boolean-logic"><em>How to optimize your LinkedIn profile using keywords so it's super easy for recruiters to find</em></a></p><h2><strong>5. Build a support network</strong></h2><p>When my company recently passed an important revenue milestone, instead of feeling proud and accomplished, one of my first thoughts was, "How am I possibly going to get this company to the next level? "</p><p>I started to imagine a host of new fears. For example, when we go public at some time in the future, how will the market respond to me? Will investors think, "Outreach is great, except I'm not sure about that CEO. He's never done this before, and he comes from Ecuador. There are no successful immigrant Latino CEOs in tech." Will having me as the CEO be detrimental to our valuation as a public company?</p><p>Well, despite the fears, the truth is that I'm pretty good at founding and scaling a company. </p><p>So rather than spend time bemoaning the unfairness of it all, I decided to put in the extra work to re-level the playing field. </p><p>Extra work doesn't just mean putting in more hours than the next person. It means being creative about preventing problems that could result from people's conscious or unconscious biases. Soon after cofounding Outreach, I set out to get 200 people in the industry to not just know me, but to respect me - for my ideas, my authentic personality, my vision. Not only did I manage to sell a lot of software to some of these people, but I also earned the trust and friendship of a network of colleagues across the industry, connections that probably saved the company during make-or-break points in our history. </p><p>I'm repeating this exercise now, this time with fund managers. We've said that we're a year or more from an IPO. But when the time comes, I want these institutional investors to know and understand me, rather than think about my heritage.</p><p>Whether it's fair or not, imposter syndrome is likely to be part of your life as a minority, immigrant or female founder. It's your choice whether you choose to let it hold you back, or to drive you forward. I encourage the latter. </p><p><em>Manny Medina is the founder and CEO of Outreach, an AI-based sales engagement platform. Prior to Outreach, Medina was employee No.3 on Amazon's AWS team and led the Microsoft mobile division from launch to $50 million in annual revenue. He holds an MBA from Harvard and a master of computer science from the University of Pennsylvania. Medina grew up in Ecuador and now lives with his wife and three children in Seattle. Follow him on </em><a href="https://twitter.com/medinism"><em>Twitter</em></a><em>.</em></p>

I'm an immigrant founder of a $1 billion tech company. Here are my 5 best tips to overcoming imposter syndrome.

<p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>Manny Medina</span></p><p class="caption">Outreach CEO Manny Medina stumbled onto a multi-million idea when his startup was nearly bankrupt.</p></div><p></p></div></div></p><ul><li><strong>Hot Seattle startup Outreach has raised another $65 million, bringing its total investment to $125 million at about a $500 million valuation, CEO Manny Medina told Business Insider.</strong></li><li><strong>This is another moment of triumph for Medina, a former Amazon Web Services and Microsoft exec.</strong></li><li><strong>This startup, his first, was on the verge of bankruptcy just a few years ago until the team's determination caused them to accidentally create a product that turned out to be a big hit.</strong></li><li><strong>Sales grew so rapidly that he convinced VCs to invest millions with one "cocky" slide, he said.</strong></li></ul><p><span><br />Outreach, a Seattle startup that offers software to help salespeople automate their work, has just raised another $65 million. </span></p><p><span>That brings its total investment to $125 million. Investors have now valued the company at about $500 million or "half a unicorn, the back half" CEO Manny Medina joked to Business Insider.</span></p><p><span>Medina is </span>known as a high-energy, cheerful leader who has memorized every employee's name, he says, and spends the first hour of the workday fist-bumping every employee in the office - even though the company is now 300 employees strong, double from a year ago, albeit not all of them work in the Seattle headquarters.</p><p>He's got reason to be happy. Back in 2015, <a href="http://www.businessinsider.com/outreach-founder-created-10-million-business-saving-nearly-bankrupt-startup-2017-6">his company was on the verge of bankruptcy.</a> In those days, his startup offered HR recruiting software that wasn't selling well. In an all-out effort to save the company, he and his team went on a sales frenzy and built a <span>work-flow app to automate the cold-calling process. The app allowed the three sales folks to spend less time digging up leads and writing initial emails, and more time in actual meetings. </span></p><p><span>The customers at those meetings still didn't want the HR tool, but they did want the automatic cold-calling app. So the company changed course and turned that home-grown tool into a product, quickly booking $1 million in sales. </span></p><p><span>When his cofounders pushed him to find some investors, Medina did so begrudgingly, he <a href="http://www.businessinsider.com/outreach-ceo-used-one-cocky-slide-to-raise-nearly-12-million-2017-7">previously told Business Insider.</a> </span>Running a business, the old-fashioned way based solely on sales, made him "very cocky."</p><p>"When you have a survivor mentality, you feel like, 'I don't need your money,'" he said.</p><p>"I had one slide. It was a chart," he said, describing his talks with VCs. "I said, 'This is our revenue growth chart. We sell to salespeople. Any questions?'" he described.</p><p>Sales were coming in so rapidly that halfway through the VC meeting, he would refresh the slide, and the sales numbers would jump. <span>The company had zoomed from $1 million to $10 million under contract just two years after almost going bankrupt. </span></p><p><span>That single slide landed the company a $2.3 million seed round, and later, the same slide landed another $9.2 million.</span></p><p><span>He then went on to raise more substantial rounds. </span><span>The latest one was led by Spark Capital with participation from a new investor, Sapphire Ventures, the VC arm of <keyword id="6356323" type="UNKNOWN" weightage="100" keywordseo="enterprise">enterprise</keyword> software giant SAP. <span style="background-color: #ffffff;">Existing investors DFJ Growth, Four Rivers Group, Mayfield, MHS Capital, Microsoft Ventures and Trinity Ventures also participated.</span></span></p><p>Medina is now positioning Outreach and his competitors as the next giant market after Salesforce - the dominant player in sales software - with customer relationship management (CRM) software. CRM is software that keeps track of customers.</p><p>"It's not going to be a new CRM that displaces CRM, but something new," he said. He calls this next thing "sales engagement" because it does more than just store lists of contacts, and actively helps salespeople handle more tasks. </p><p>VCs are apparently agreeing with him. Other sales automation tools are raising big bucks as well, Medina points out, including InsideSales, which has raised about $300 million (and is being watched for signs of an IPO) and Intercom, which has raised about $240 million.</p><p>Medina no longer uses the single "cocky" slide when raising money, but he did share it with us. It shows one metric: the company's monthly recurring revenue ("MRR").</p><p> </p><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>Outreach</span></p><p class="caption">Outreach Series C slide.</p></div><p></p></div></div></p>    <div class="margin-top">        <h3>NOW WATCH: <a href="http://www.businessinsider.com/nobel-prize-winning-economist-oliver-hart-what-milton-friedman-got-wrong-2018-5">A Nobel Prize-winning economist explains what Milton Friedman got wrong</a></h3>        <div>                    </div>    </div>

The CEO who raised millions with just one 'cocky' slide landed another $65 million - and his company is now worth half a billion dollars

<p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span><a href="https://unleash.outreach.io/sessions-2017.html#keynote">Outreach</a></span></p><p class="caption">Outreach CEO Manny Medina</p></div><p></p></div></div></p><ul><li><strong>Manny Medina is the CEO of a hot and fast-growing Seattle startup called Outreach.</strong></li><li><strong>Through its rapid growth, Medina has, so-far, maintained a 100% approval rating on job-hunting site Glassdoor.</strong></li><li><strong>He explained several reasons why he thinks this is so: he goes to great lengths to interact with his 300 employees in direct, personal and humanizing ways.</strong></li><li><strong>He shared his three tips that any manager can do to create a happier team.</strong></li></ul><p><br />Manny Medina is the CEO of a hot Seattle startup called Outreach. The company is growing like gangbusters, from about 170 employees and 1,200 customers a year ago to about 300 employees and 2,400 customers today.</p><p>And <a href="http://www.businessinsider.com/outreach-raises-65-million-is-now-worth-half-a-billion-dollars-2018-5">Outreach just raised another $65 million</a> ($125 million total raised so far) to fund more growth, too.</p><p>Medina is a former exec from Microsoft and worked, back in the day, at Amazon on the team that founded Amazon Web Services, Amazon's juggernaut cloud computing service.</p><p>But this is his first run as a CEO and founder. Often, when startups grow this fast, particularly under their founder CEOs, they hit predictable growing pains. As employees pour into the org, communication plummets. Then project management suffers, the right hand stops knowing what the left is doing, and employees grow frustrated and start complaining about the company and its management.</p><p>But for now Medina has a perfect 100% rating on Glassdoor while 97% would recommend the company to a friend. He knows that his perfect CEO rating probably won't last forever, that it will be impossible to keep everyone happy all the time.</p><p>Still, he shared some tips with Business Insider to help explain why his rating is so high and to give other managers useful advice to keep their team as happy as possible.</p><p>1. <strong>He personally greets every employee every morning, walking through the office to see everyone. </strong></p><p>Medina is a high-energy, cheerful sort of guy, so his greeting comes in the form of a fist bump to each an every employee he sees when he comes into the office in the morning.</p><p>He began the tradition when the company was tiny and struggling to stay alive. The fist bump was a way to raise spirits, determination and energy, he told us. </p><p><div class="KonaFilter image-container display-table float_right"><div><div class="image on-image"><p class="source"><span><a href="http://www.apimages.com/metadata/Index/Obama/46f0449f60784b44a6eb36054f906a00/6/0">AP Photo/Robert F. Bukaty</a></span></p></div><p></p></div></div>"It's a way to look everyone in the eye and say, 'We're going to kill it," Medina told Business Insider. "It creates the connection, early in the morning, when there's not a whole lot of noise."</p><p>It worked, too. The company turned around in 2015 and has been going gangbusters ever since.</p><p>Even now that the company is 300 employees (not all of them located at the headquarters office), he continues morning fist-bump tradition.</p><p>A fist bump might not be every manager's style, but the basic premise of a cheerful daily greeting to every person on the team before the day runs away can be adapted by anyone.</p><p>When you smile, it boosts your mood and the mood of the people you've smiled at. It makes you appear more courteous and likeable, and, most surprising, it also makes you appear more competent, <a href="https://www.psychologytoday.com/us/blog/changepower/201605/the-9-superpowers-your-smile">research from the University of Missouri-Kansas City found.</a></p><p><strong>2. He learns people's names. </strong></p><p>"I do make an effort to memorize everyone's names. I know 300 first names and you can test me on that," he laughed. Obviously, the more people a manager oversees the more difficult it is to memorize everyone's names. But research shows that our brains become <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1647299/">more engaged when we hear our first names.</a></p><p>So, to the extent that this is possible, it's worth the effort to learn as many names as possible.</p><p><strong>3. He sends a weekly email of personal thoughts which humanizes him and the job of CEO. </strong></p><p>"I send an email to the entire company every Sunday: How did my week go? What did I learn? Maybe a shout out. The emails are my point of view, where I just talk about what happened that week, top of mind, as if we had a beer together," he said.</p><p><div class="KonaFilter image-container display-table float_right"><div><div class="image on-image"><p class="source"><span>Manuel Medina linkedin</span></p><p class="caption">Outreach IO CEO Manuel Medina</p></div><p></p></div></div>Medina told us that as the company has grown, and his job as CEO has grown, he has wanted to drop the email, as it was cutting into his time with his family. He mentioned his desire to drop the email to his CMO and the CMO told him not to stop it until they polled the employees.</p><p>"85% of the employees said they read the letter and didn't want it to stop, and the other 15% didn't answer the survey," he said. That clinched it. Employees liked it, so the email stayed.</p><p>Whether a weekly personal email is your style or not, the lesson here is that regular, personalized communication is the cornerstone of good communication. And this is not "messaging," although good leaders do need to be articulate the company's mission and priorities and repeat those messages often. This communicating is about interacting as a fellow human being, helping your staff understand why you make the decisions that you make.</p><p>Research shows that good communication has a massive impact on the workplace. </p><p><a href="https://www.roberthalf.com.au/blog/employers/happiness-work-it-natural-or-necessary">Robert Half's Happy Work report</a> finds that managers who communicate well create camaraderie and that camaraderie leads to happier, more engaged employees.</p>    <div class="margin-top">        <h3>NOW WATCH: <a href="http://www.businessinsider.com/what-happens-next-north-south-korea-peace-treaty-2018-4">What will probably happen with the North and South Korean peace treaty</a></h3>        <div>                    </div>    </div>

This tech CEO shares his secret for his 100% approval rating on Glassdoor - and any manager can do it

<p><span></span></p><p class="source"><span>Manny Medina</span></p><p class="caption">Outreach CEO Manny Medina stumbled onto a multi-million idea when his startup was nearly bankrupt.</p>Back in 2015, Outreach CEO Manny Medina had just brought his startup back from the brink of bankruptcy.<p><span>Medina's cofounders, Gordon Hempton, Wes Hather and Andrew Kinzer, had whipped up some home-grown software to automate the cold calling process so that Medina's three-person sales team could operate like a team of 20. </span></p><p><span>It worked really well and they went on a lot of sales calls but no one wanted their startup's HR software. Everyone wanted that homegrown sales tool. So the team changed course, turned it into a product and managed to quickly sell nearly $1 million worth.</span></p><p><span>Medina was keeping the company afloat the old fashioned way, from revenues, and he didn't want to bring in investors. </span>But his cofounders, exhausted from living hand-to-mouth, convinced him to try and raise money. </p><p>He did his VC tour begrudgingly. Fighting off bankruptcy made him "very cocky. When you have a survivor mentality, you feel like, 'I don't need your money," he told Business Insider. </p><p>"I had one slide. It was a chart. I said, 'This is our revenue growth chart. We sell to sales people. Any questions?'" he recalled.</p><p>The slide had one word on it "MRR" which stands for monthly recurring revenue. "[It was] <span>a screenshot of Recurly, the subscription payment service we were using at the time. </span><span>I presented it and then I would do this trick: I would refresh the screen mid-pitch, and be like 'Oops, sorry, revenue just went up while we were talking."</span></p><p>That single slide landed the company a $2.3 million seed round and later,<span> the same slide landed another $9.2 million Series A round led by Mayfield. And with that money the company grew to $10 million in annual recurring revenue by the end of 2016, Medina told Business Insider.</span></p><p>Medina has since given up his cocky attitude and raised another $30 million in 2017 (for a total of $59 million in raised capital) and now counts DFJ Growth and Microsoft Ventures among its investors.</p><p>Here's the slide:</p><p class="source"><span>Outreach</span></p><p class="caption">Outreach Series C slide</p>            <h3>NOW WATCH: <a href="http://www.businessinsider.com/tesla-model-x-america-electric-car-road-trip-elon-musk-2017-6">We drove a brand-new Tesla Model X from San Francisco to New York - here's what happened</a></h3>                                    Please enable Javascript to watch this video

A startup CEO used one 'cocky' slide to raise nearly $12 million - here's what it looked like

<p><span></span></p><p class="source"><span>Manny Medina</span></p><p class="caption">Outreach CEO Manny Medina stumbled onto a multi-million idea when his startup was nearly bankrupt.</p>Manny Medina, the CEO of fast-growing startup Outreach, is so happy with his company that he gives a fist bump to every employee every morning.<p>Outreach employs about 170 people, so some mornings, this ritual can take him nearly an hour.</p><p>"All things being equal, the one thing that you can really manage on a day-to-day basis is the energy," he told Business Insider.</p><p>Today Outreach counts about 1,200 companies as customers and hit annual recurring revenue of $10 million by the end of 2016, just two years after its sales automation product was released, he said.</p><p>And it all happened because three years ago the startup was on the brink of bankruptcy, with two months cash in the bank.  </p><p>Back in June, 2014, his startup was called GroupTalent, it sold recruiting software, and things weren't going well. </p><p>Faced with a choice of winding down or doubling down, Medina ordered his team to go on a sales frenzy. He launched his career as an early Amazon Web Services employee and then did a seven-year stint at Microsoft and wasn't about to give up.</p><p>"It was myself and two salespeople and we needed to execute like a team of 20 to get our sales out of the hole," he told Business Insider. </p><p>Medina's cofounders, Andrew Kinzer, Gordon Hempton, weren't sales people, but they were product people. So they built a work-flow app to automate cold calling, helping the three people find more leads and book more meetings. </p><p>The tool automatically did follow-up emails. Better still, "it allowed us to plug in a set of writers so that they could personalize the emails," he described.</p><p>That meant that all the cold calls were written by real people, professional freelance writers who could do things like add a reference to the person's home town or hobbies and such.</p><p>The emails worked, capturing people's attention and the team booked a bunch of meetings. But people weren't that interested in the recruiting tool. They wanted to know about those appealing cold-call emails.</p><p>"People were like, I don't want to buy your recruiting product. I want to buy your sales tool. And that was the birth of Outreach," he said.</p><p>The startup put their recruiting tool on the back burner and concentrated on converting this homegrown thing into a real product. It launched in January, 2015.</p><h2>Some unexpected help</h2><p>Still, the company's current growth wouldn't have happened without another stroke of luck for Medina.</p><p>One of those early meetings had been with Mark Kosoglow, today the company's VP of sales. He didn't buy the recruiting product either but he and Medina hit it off, became friends and Kosoglow began to mentor Medina on how to be a better sales person.</p><p class="source"><span>Outreach</span></p><p class="caption">Outreach employees</p>One day, Kosoglow offered to come work for Medina.<p>"I said, I would love to hire you, but I don't have any money," Medina recalls. </p><p>Undeterred, Kosoglow offered to work on commissions only. "Then he turned around and convinced four of his friends to do this job commission only, too. And that was our first sales team. We got to $1 million on the back of that."</p><p>And that fast success helped them reel in VCs ready to invest. Outreach has raised $59 million total and is valued at $200 million, <a href="https://my.pitchbook.com/profile/99300-34/company/profile#deal-history/88052-50T">according to PitchBook,</a> the website that tracks such things.</p><p>Those early years of fighting off bankruptcy made him "very cocky. When you have a survivor mentality, you feel like, 'I don't need your money," he said.</p><p>So for his last round, "I had one slide. It was a chart. I said, 'This is our revenue growth chart. We sell to sales people. Any questions?'" he said.</p><p>Apparently not. Outreach raised a $30 million round in May, led by DFJ Growth, with participation by existing investor Mayfield as well as Microsoft Ventures and others.</p>            <h3>NOW WATCH: <a href="http://www.businessinsider.com/inventor-roomba-behind-roomba-for-gardens-2017-6">The inventor of Roomba has created a weed-slashing robot for your garden</a></h3>                                    Please enable Javascript to watch this video

By desperately trying to save his nearly bankrupt startup, this guy accidentally found a $10 million idea

<p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>AP</span></p><p class="caption">A Facebook partner lounges on Facebook's Menlo Park campus.</p></div><p></p></div></div></p><ul><li><strong>The least-secret secret in the Valley is called "resters and vesters," or "coasters" - which refers to engineers who get paid big bucks without doing too much work, waiting for their stock to vest.</strong></li><li><strong>We talked to engineers in the "rest and vest" world who explained how it happens and how they spend their days.</strong></li><li><strong>As cushy as it sounds, there are some real career risks and pitfalls for doing this rest-and-vest thing.</strong></li></ul><p>On a sunny summer morning, a Facebook engineer woke up to go to work but felt ill. She ran to her bathroom and threw-up. "I thought I was getting sick," the engineer recalled. </p><p>It wasn't a virus or food poisoning. She was having a bad reaction to her job.</p><p>She was making $1 million a year, mostly in stock, and running a team of about three dozen people, she told Business Insider. And she had worked herself into a state of exhaustion in the three years since Facebook had acquired her previous company. The acquisition had been highly political, the integration wasn't going well and she had been killing herself to make it more successful and protect her people from losing their jobs over it.</p><p>As tired as she was, she couldn't just quit this job. She owed a big chunk of money in taxes thanks to that stock and needed her salary to pay those taxes.</p><p>But after getting violently ill at the thought of going to work, she decided not to go in. Not that day. Not ever again. And she knew she wouldn't get fired.</p><p>Because not going to work was actually her manager's idea.</p><p>The previous day she had told him she would be leaving the company at the end of the year, six months away. She wanted to spend the rest of the year wrapping up her projects but not taking on any more, collecting on the stock that would vest by year end and making the money she needed to pay her taxes.</p><p>"My manager and I had lots of conversations. I teetered on leaving so many times," she said. "But this time was for real. I was going to see these projects to a healthy state and then I needed to go. I felt good about it. The next thing, he told me not to come in."</p><p>She panicked thinking he was firing her but he explained she wasn't being terminated at all. "Just don't come to work. You're burned out and need a break. Just don't talk about it and everyone will assume you're on someone else's team," her told her.</p><p>The manager's proposal didn't go over well. "I was livid and I never would have done it. I had every intention of joining another team. But then I woke up and started vomiting," she said.</p><p>And that's how this hard-working, conscientious engineer wound up joining the least-secret, secret club in the Valley, known as "rest and vest."</p><h2><strong>The least-secret, secret club in Silicon Valley</strong></h2><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span><a href="https://www.flickr.com/photos/laughingsquid/2910041631/in/photostream/">Scott Beale/Laughing Squid</a></span></p></div><p></p></div></div>"Resting and vesting" is when an employee, typically an engineer, has an easy work load (if any job responsibilities at all) and hangs out on the company's payroll collecting full pay and stock. Stock is often the bigger chunk of total compensation for a senior engineer than salary.</p><p>Once she was in rest-and-vest mode, this engineer spent her time attending tech conferences, working on pet coding projects and networking with friends, quietly developing an idea for her next gig, a startup.</p><p>She realized that her manager let her "rest and vest" to keep her quiet about the problems with that acquisition, so she had time to find her next thing. Had he terminated her immediately, she would have been incensed. "Everyone knew I had a big mouth and would speak out. He figured, 'Hey, it costs us next to nothing keep her happy for six months,'" she said.</p><p>Business Insider talked to about a half a dozen people with direct knowledge of the rest-and-vest culture. Some were "fat cats" themselves. Some were hiring managers who tried to lure these folks back to the world of productivity. Many acknowledged that resting and vesting was a common, hush-hush practice at their own companies. Internally, these people are often referred to as "coasters."</p><p>Their lives counter the other reality for many in the tech world: <a href="http://www.businessinsider.com/syndromes-drive-coders-crazy-2014-3">long work hours</a> and pressure for workers to pledge unrelenting devotion to <a href="http://www.businessinsider.com/why-this-google-engineer-gave-up-on-silicon-valley-2017-3">their companies and jobs above all else.</a></p><h2><span>'My days began at 11 ... and I took long lunches'</span></h2><p>Engineers can wind up in "rest and vest" jobs in a variety of ways. </p><p>Manny Medina, the CEO of fast-growing Seattle startup <a href="https://www.outreach.io/">Outreach</a>, has been on all sides of it. He briefly was a coaster himself, and says he saw how Microsoft used it to great effect when he worked for the software giant. He has also tried to lure some "rest and vest" engineers to come work for him at his startup.</p><p><div class="KonaFilter image-container display-table float_right"><div><div class="image on-image"><p class="source"><span>Manny Medina</span></p><p class="caption">Outreach CEO Manny Medina experienced the "rest and vest" phenom from all sides.</p></div><p></p></div></div>Medina said he experienced the high-pay, no-work situation early in his career when he was a software engineer in grad school. He finished his project months early, and warned his company he would be leaving after graduation.</p><p>They kept him on for the remaining months to train others on his software but didn't want him to start a new coding project. His job during those months involved hanging out at the office writing a little documentation and being available to answer questions, he recalls. </p><p>"My days began at that point at 11 and I took long lunches," he laughs. "They didn't want you to build anything else, because anything you built would be maintained by someone else. But you have to stand by while they bring people up to speed."</p><p>Years later, he landed at Microsoft and says he saw how Microsoft used high-paying jobs strategically, both within its engineering ranks and with its R&amp;D unit, Microsoft Research. The company, he says, would nab hard-to-find experts in up-and-coming fields like artificial intelligence, robotics, natural speech language, quantum computing and so on, often allowing them to collect their Microsoft pay while maintaining a job as a professor or researcher at a university.</p><p>"You keep engineering talent but also you prevent a competitor from having it and that's very valuable," he said. "It's a defensive measure."</p><p>Another person confirmed the tactic, telling us, "That's Microsoft Research's whole model."<strong> </strong></p><h2>'Mid-30's pulling in 7-figures a year'</h2><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>AP</span></p></div><p></p></div></div></p><p>At other companies it's less about defense and more about becoming indispensable.</p><p>For instance, Facebook has a fairly hush bonus program called "discretionary equity" or "DE," said a former Facebook engineer who received it.</p><p>"DE" is when the company hands an engineer a massive, extra chunk of restricted stock units, worth tens to hundreds of thousands of dollars. It's a thank you for a job well done. It also helps keep the person from jumping ship because DE vests over time. These are bonus grants that are signed by top execs, sometimes even CEO Mark Zuckerberg himself.</p><p>"At Facebook the 'OGs' [Original Gangsters] we know got DE," this former Facebook engineer said. OGs refer to engineers who worked at the company before the IPO. "Their Facebook stock quadruples and they don't leave. They are really good engineers, really indispensable. And then they start to pull 9-5 days," this person said. </p><p>Facebook declined to comment but several engineers told us that Facebook has a reputation of requiring long hours from their engineers.</p><p>These DE bonuses are not specifically designed as a mechanism for resting and vesting, but they can play a role in enabling it. Those with DE packages land in a self-fulfilling prophecy of success. They become known to top managers. They get choice assignments with plenty of resources which means they can work less with good outcomes, this Facebook engineer described.</p><p>"These are really smart people and they don't leave. They're in their mid-30s, pulling in seven figures a year, and they don't have to work as hard. We say they're just coasting," he said.</p><h2>The 10x engineer</h2><p>Other "rest-and-vest" types are part of a tribe in the Valley known <a href="http://redmonk.com/fryan/2016/12/12/on-the-myth-of-the-10x-engineer-and-the-reality-of-the-distinguished-engineer/">as "the 10x engineer,</a>" a term used to describe someone said to be 10-times more effective than a so-called ordinary engineer.</p><p>Legend has it that a 10x engineer can do in one hour what it would take others 10 hours to do. Some of these folks are just plain brilliant. Others aren't necessarily smarter but they know every detail of a critical system. </p><p>"When people have been there long enough, they often bring a value that's not easy to see. They might know where the bodies are buried on some project, be called in as a last resort to debug a project, or they are known as a great pinch hitter," describes the former rest-and-vest Facebook engineer.</p><p>"One guy at Facebook didn't seem to work a lot, but when the site would go down he could find things that couldn't be found," the engineer described.</p><h2>Google and the "rest and vest" joke</h2><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>BI Graphics/Anaele Pelisson</span></p></div><p></p></div></div>Other members of the "rest and vest" set are the "coasters," the long-timers who have reached a company's top engineering ranks and don't need to work hard to stay there.</p><p>They may not be 10x engineers, but they are institutional employees who know how to do just the right amount of work to get a good annual review and collect their next batch of stock grants.</p><p>According to all the folks we talked to, Google is known as a place where this type of rester-and-vester flourishes.</p><p>"Most of my friends at Google work four hours a day. They are senior engineers and don't work hard. They know the Google system, know when to kick into gear. They are engineers, so they optimized the performance cycles of their own jobs," one engineer described.</p><p>A former Google manager who recently left the company agreed. "There are a lot 'coasters' who reached a certain level and don't want to work any harder. They just do a 9-5 job, won't work to get promoted, don't want to get promoted. If their department doesn't like them, after a year or two they move somewhere else," she said.</p><p>The term "rest and vest" even became a term jokingly associated with Google when HBO's satire sitcom, "Silicon Valley" did a bit on it. In the hit show, Nelson "Big Head" Bighetti, played by actor Josh Brener, got a promotion at the fictional tech giant Hooli, which is inspired by Google. Bighetti was not assigned to any project and instead joined a group of other unassigned employees squandering their days on the company's roof.</p><p>"I've actually had a number of people, including today at Google X, ... send me pictures of themselves on a roof, kicking back doing nothing, with the hashtag 'unassigned' or 'rest and vest.' It's something that really happens, and apparently, somewhat often," the actor <a href="http://www.businessinsider.com/silicon-valley-rest-and-vest-2016-8">Brener told Business Insider's Melia Robinson last year.</a></p><p>While those pictures were likely jokes sent to Brener by fans of the show, several people from Google told us that when very senior engineers wrap up a big project, they may find themselves unassigned for a while, reporting to Google cofounder Larry Page, until they decide what they want to do next, not unlike the Hooli roof-top crowd.</p><h2>"<span>Life is good, you maximize your vacation. I'll come in when I want to"</span></h2><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>Getty/Stephen Brashear</span></p></div><p></p></div></div>The moonshot research unit known as X, run by Google's parent company Alphabet, has a Valley-wide reputation as a place to land a "rest and vest" gig, several people told us. </p><p>An engineer currently working at X said that X's extremely long-term view, and its tendency to cancel projects, has given it that reputation.</p><p>"At X, we don't have a sense of budgetary concerns," this person said. "Engineers get paid $250,00 to $600,000 range, but there's no sense of urgency. It's like a startup but not really. It's like a startup with unlimited funds."</p><p>Alphabet's CFO and Wall Street veteran Ruth Porat is said to be reining in the idea of unlimited funds at X and elsewhere in the company.</p><p>People inside Google say that her office personally approves all new hires these days for all units except cloud computing, which reports to Diane Greene. (We hear cloud is growing so fast that Google is ramping investment in it, hiring like crazy.)</p><p>Even so, it's the nature of X that can tempt people into coasting, this engineer says.</p><p>While other tech companies "sear" a product's ship date into their engineers, who work nights and weekends to hit that date, "at X, people think, 'if my project is cancelled, oh well, I'll just find another project,'" he said.</p><p>"You get paid so much after a certain level at Google, that once you get there, there's no real reason to work that hard. Life is good, you maximize your vacation. I'll come in when I want to," the X engineer said, estimating that very senior engineering positions can command up to $400,000- $600,000 in total compensation at X, including bonus and stock options.</p><p>"What incentive do you have to work harder when you are already making $500,000 in salary and there is no more upward trajectory?" this person explains.</p><p>Google declined comment but a spokesperson for Alphabet X wholly rejected this characterization.</p><p>"W<span>e have a compensation program here that has been tailored to encourage intellectual honesty from our teams," X spokesperson Courtney Hohne told us. "So we developed this program to reduce any incentives to just hang around until some far-off payday."</span></p><h2>Come to work each day and play</h2><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span>REUTERS/Erin Siegal</span></p><p class="caption">An employee plays with Legos at the New York City offices of Google</p></div><p></p></div></div>Whether coasting long term, unassigned short-term or resting-and-vesting for another reason, these engineers typically do go into the office every day and are expected to show up, a former Google manager told Business Insider. </p><p>"You have to be physically present," this person said. But "there are so many distractions within Google" that it's easy to come to work and still spend hours playing.</p><p>"You want to have lunch at a lovely cafe, or maybe attend a tech talk, or a class, or you want to go to a bodywork class at 6 p.m. or to get juice at the Slice Cafe and it's on another campus. So you end up working 6 hours. There are times you have to put in nights and weekends, but in general, the company is so big and has so much money, you can work less," this person told us.</p><p>Google certainly isn't the only tech company to offer such distractions. <a href="http://www.businessinsider.com/facebooks-disneyland-inspired-campus-2013-10">Facebook has classes, a wood shop</a> and a video arcade for its employees. Oracle <a href="http://www.businessinsider.com/oracle-employees-enjoy-pool-yacht-2015-1">has a sand beach volley ball pit and a swimming pool</a>. Microsoft has a soccer and cricket sports field, <a href="https://careers.microsoft.com/benefits/usbenefits">plenty of Xboxes and an on-site day spa.</a> We've been told rest-and-vest engineers can be found at all of these companies.</p><h2>From cushy to dead-end </h2><p><div class="KonaFilter image-container display-table"><div><div class="image on-image"><p class="source"><span><a href="http://www.apimages.com/metadata/Index/Happy-Happy-Worksite/f99af0ed6be44b7faa44531eb8d3fc74/110/0">AP Photo/Jeff Chiu</a></span></p><p class="caption">Companies say extraordinary campuses are a necessity, to recruit and retain top talent, and to spark innovation and creativity in the workplace. And there are business benefits and financial results for companies that keep their workers happy.</p></div><p></p></div></div>If this sounds like a dream job situation, there is a dark side: the "rest and vest" life can also be a career killer. </p><p>In an industry that worships workaholics and the Next Big Thing, ambitious engineers want their resumes to be full of products used by millions of people.</p><p>But rest-and-vest engineers can wind up spending years "never shipping anything" the X engineer described. That can be particularly true for those coasting at a long-term research facility like Microsoft Research, where <a href="http://www.businessinsider.com/google-x-yoky-matsuoka-valley-of-death-product-development-2017-7">academic research doesn't easily leap into commercial products</a> or at X, <a href="https://www.nytimes.com/2016/07/24/technology/they-promised-us-jet-packs-they-promised-the-bosses-profit.html">where projects are frequently cancelled</a> by design.</p><p>"They know staying at X can be a career deadpool," the X employee said.</p><p>X spokesperson <span>Courtney </span><span>Hohne says that this criticism misses the point of X.</span></p><p>"<span>X is not about polishing products or optimizing systems that support millions of users," Hohne said. "X is designed to be a place for early stage prototyping and de-risking. Different engineers (and business people) like different stages of the innovation process, and that's ok."</span></p><p>Still, Medina, the former coaster and Outreach CEO, agrees that doing the rest-and-vest thing too long can be dangerous for a career.</p><p>"These engineers are highly, highly paid, but there is no other company that will take them," he says.</p><p>If the engineers are willing to adjust their pay expectations downward and roll up their sleeves again, startups like his have been known to offer them jobs.</p><p>"Eventually, they get tired and want to go get real work," he said.</p><p class="tagline">Get the latest Google stock price<a href="http://markets.businessinsider.com/stock/GOOG-Quote"> here.</a></p>    <div class="margin-top">        <h3>NOW WATCH: <a href="http://www.businessinsider.com/apple-iphone-8-rumor-roundup-iphone-x-10-rumors-tim-cook-2017-8">Everything we know about the new iPhone that Apple will announce in September</a></h3>        <div>            <div>        <div class="ooyala-video-player" data-video-autoplay="false" data-video-id="mhKLRarl" data-player-variable="ooyalapopvideo" id="ooyalaplayer_popvideo" style="width:1280px;height:720px"></div>        </div>        </div>            </div>

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