Rafat Ali is best known for his coverage of the New York tech scene -- which he’d done since the dot-com boom went bust. However, what’s amazing is that he began his working life as a computer engineer, pre-internet in India and found his way into the industry at large by way of a Masters Degree from Indiana University and a personal blog. It’s because of these experiences that he found himself humbly rising the ranks during a tumultuous time at the frenzied start up Inside.com, and finally made his way to covering the industry itself with Jason Calacanis's Silicon Alley Reporter (just as it's own print publication went bust). Eventually, and seemingly accidentally, he turned his side project, paidcontent.org (terrible name and all), into a must-have for media professionals before even more accidentally turning that into a surprising and swift exit. His experience sums up the evolution of New York new media.   Now as the CEO & Found of his latest project, Skift, Rafat is using the knowledge he's gained along the way to create a truly profitable journalism product that covers the biggest industry in the world - travel - from a b2b perspective. We’ve learned that years in, Skift is in the black and has three equal revenue streams that give Rafat and his team the runway to build the company that works the way they want it to in a way that benefits both users and advertisers alike. Cheers! For more from him, follow @Rafat.

As we’ve learned about the tech industry thus far, the road to success is usually unpaved. This week we learn that becoming a VC is not dissimilar. Ellie Wheeler is a principal at Greycroft Partners, where she is a seed investor and has been investing in the tech industry for almost four years. However, getting here was not an easy or clear path, in fact, one that she didn’t even know existed. What it took was dropping out of medical school, balancing the world of Private Equity and major corporate M&A, a business school degree and exposure to the startup world filtered through Chris Sacca. Her story is a meticulous experience of writing and rewriting checklists that have helped her get to whatever next step she needed to make.   Over a couple glasses of xx Pinot Noir, Ellie shared with us the method to her madness; how in her experience, she has been able to develop a set of standards and keys for success for any startup in this industry, as well as a list of red flags. This, of course, is critical to her as an investor, as she has her finger on the pulse of business and sees trends come and go every six months. And this, of course, is critical to anyone in the early stages of the tech industry -- as founders and investors -- who are looking to be meticulous in their next steps as well. For more insights, check out @Ellie on Twitter.

Early in his career, David Kassan lead a double life: interactive art director by day and painter by night. While designing and quickly rising through the ranks of one of the world's largest consulting companies, iXL, and later at an indie music startup during dot-com 1.0, he was simply “paying the bills.” It was when things went awry in the dot com burst, that David made the bold move to pursue his passion and threw his whole effort into painting professionally. He has never looked back. Fortunately, he did so with a solid foundation; an innate artistic ability, a fine art background from Syracuse University, and gallery representation at a major Chelsea gallery starting at age 21. It was this catalyst which lead to an unpredictable career path.   Over a couple Sixpoint beers we learned that since then, technology has followed David. From early iPad innovation and real-time painting videos helping him achieve temporary internet fame, to launching his own revolutionary design for the Palette on Kickstarter, to the interconnectedness the internet has afforded the art world, the surprising lessons David draws from his time in tech, how it impacted his painting and vice versa remain valid today for all visual, UX and product designers alike. And, of course, his position on the age old debate -- is product design art? Check out David’s work here or give him a shout on Twitter at @DavidKassin.

Spoiler alert: Caroline McCarthy ended up in tech despite her best efforts to avoid it. It’s true. After sitting down over Pine Barrens whiskey she shared her story of having an innate interest in tech, but after experiencing the isolating and stereotyping that comes with being “that kid” in school, repressed it in favor of just about anything. Not without accolades, of course, this Princeton University graduate (with a degree in the History of Science - what?) and champion rower, found herself without real direction upon graduation. In an effort to pursue her lifelong interest in writing, she entered the working world as a journalist for CNET, covering the budding tech startup scene in New York City. And that was when the gig was up and she was catapulted back into the world she could no longer actively avoid.   Years later her career boasts more than her long standing tech journalism career, but a tech marketing gig at Google, as well, working on projects like Google+. However, after seeing how the industry works on both of these, often very opposing sides, she has decided to join a “startup like” company where she is able to make lasting change. These days you can find Caroline fighting the good fight as  the Vice President of Content & Communications at True[X], where she is helping to help pioneer the future of media and call out the too old smoke-and-mirror games played by the digital display world… and trying to solve for what comes next. For more from Caroline (and, at the very least, cute photos of her cat Caterpillar): @caro

One of the biggest, and often overlooked, challenges in product and brand building is that of identifying your audience, but beyond that, is reaching that audience. As technology advances and “touch points” are exponentially increasing, as consumers become more savvy, and as companies are being held accountable for their communications, the ecosystem only becomes more and more complex. This week we had the great pleasure of meeting with media strategy extraordinaire, Connections Associate Director at MediaVest, Chris O’Leary, who broke it down for us; how to derive the best value for your advertising budget, the difficulty of measuring against new technologies (::cough cough:: mobile) and the benefit of new platforms, and how we’re poised, more than ever, to actually fulfill those “personas” of advertising yore. Over beer selections from Westbrook (One Claw and White Thai), Chris explained his path to media expertise; how studies at Ithaca College in Television-Radio/Media Management and his early desire to become a journalist (met with a harsh job market) turned to a career in media. With experiences spanning from a 40 person agency in Burlington, Vermont to 9-figure budgets in New York City, he has sharpened his mind to determine the best way to communicate a brand’s message to the right audience in the right place at the right time. And, of course, marrying that experience to his love of craft beer, leading to the establishment of Brew York (bringing all things craft beer to the masses of New York). But, truly, what chops would he have if he didn’t seize the perfect moment at the intersection of media and technology to have the ultimate viral selfie. For all things beer and media (not necessarily in order of importance), see @ohhleary.

It’s our opinion that the best entrepreneurs, very simply, are greater than the sum of their experiences, and have found the best ways to extract value from each. Case in point: Caroline Waxler. In her career, Caroline has spanned many industries and roles, starting in the mailroom at Newsweek and using it as a springboard, she ultimately rose through the ranks of the publishing world, working for titles like Forbes and Cosmo. However, she didn’t stop there, and expanded her horizons, both physically and professionally, by moving across the country, she ultimately established herself as a “name” in the freelance writing world. Since then, her writing has transcended the traditional publishing route and has manifested in the form of several highly acclaimed books (see: “Stocking up on Sin”) and successful comedy shows (see: Best Week Ever). But when that wasn’t enough, Caroline joined LearnVest at the ground floor, which is where a spark ignited and she was inspired to create something of her own. So when Caroline joined us for a custom, Story in a Bottle concoction of Sauvingon Blanc, bitters, soda, and fresh orange juice, (henceforth, the Waxler), she shared with us how creative callings rarely follow direct paths. It’s this pursuit and culmination of experiences which has lead Caroline to be the very capable Founder of Harkness Hall, a conference programming and digital strategy company based in NYC and has helped companies including Google, Forbes, Condé Nast, and Advertising Age program their brilliant live events. (And we couldn’t think of someone with a more qualified background to do it -- no joke.) For more from her, holler at @cwaxler.

In the ecosystem of the startup and tech world, VCs play a vital role to keep the community vital and flourishing; with the ability to coach along the best and brightest into the future, they help to cultivate innovation in many ways. Amongst them, Steve Schlafman is a natural leader. Steve is a Principal at RRE Ventures, focusing on early stage companies in mobile services, hardware, and marketplaces and what he brings to the table is a level of experience and business savvy that is truly impressive.   Steve joined us for a trio of tripels** and helped us dissect this often elusive piece of the business. From his seemingly accidental path into the investing world by way of a love of Nintendo as a kid, to Northeastern University (with an amazing co op program which encourages students to have real world experience while studying), to a stint with Microsoft and the New England Patriots, and eventually getting his foot in the door at Lerer Ventures, he has been able to refine his knack for successful business ventures and worthy founders. He explained to us why sometimes even the best ideas get passed over for 2 rounds of funding only to ultimately receive his support and what makes a standout founder in this day and age. If you are in any stage of raising, consulting, or pursuing a portfolio of your own, his is a perspective worth investing in.   For more from Steve, consult @schlaf on Twitter and check out his Guide to NYC Tech and Raising a Seed Capital. **Allagash, St. Bernardus, and Westmalle Trappist

Christina Wallace is a tried-and-true “jack of all trades.” A self-prescribed generalist, she’s made the successful leap through many different industries and roles; from degrees in mathematics and theater from Emory, to “diva management” at the opera, to Harvard Business School and founding her first company, Quincy. And while her path was winding, it’s very much by design. Refusing to focus, she’s set out to “do” all of the things she loves, drawing parallels where they exist, which have ultimately culminated as her dream job as the Founding Director of BridgeUp: STEM, a new educational initiative at the American Museum of Natural History focused on introducing girls and minorities to computer science.   But no great story is without its challenges. Over whiskey gingers, Christina gave her candid account of how to make it work and what she did when it didn’t (like at a $1MM company that was failing, for example). She reminds us to be resilient, what REAL networking is, and proof of the power of the Violence of Articulation. And through her efforts, she continues to inspire us that the future of tech is a bright one.   For more on BridgeUp: STEM, which has it’s first cohort of new after-schoolers starting this month, see: http://www.amnh.org/learn-teach/grades-9-12/bridgeup-stem/brown-scholars And, of course, hit up @cmwalla. Tell her we sent you.

Matt Lee is currently a Senior Usability Researcher for Booking.com, but in his remarkable career, he has played many other roles: a Business Administration graduate, a field researcher representing companies like Cannon… and Vicodin, a Usability Engineer for the first Xbox live and Amazon, and User Researcher Manager at Zappos. More than that, however, he is a true advocate for the betterment of the internet, championing the important learnings he has acquired about user behaviors and bringing them to the forefront of each product he’s worked on.   In this episode, we sit with him over a bottle of Hibiki (a Japanese Suntory Scotch) and we hear his story; the good, the bad, and the very very awkward moments that come along with user research. What we learned, is how the digital world is changing; from people not knowing how a mouse works (seriously) to the exponential growth from products to devices and how data can and should be at the core of all innovation. He maintains that more than ever before  “it’s less about getting from A to B.” So, if you’re building a new product or growing an existing one -- you’ll certainly want to hear this. And if you want even more from him, hit him up @mleeconsulting.

This week is another first for Story in a Bottle; for the first time we are hearing the point of view of the arguably unfairly named redheaded stepchild of the internet, social media. (We’ll pause while you process that.) But seriously, who better to represent it than one of the internet’s most beloved redheads, Lindsay Kaplan?   Lindsay joined us for Glenmorangie scotch and shared her experience of growing into the world of social media and communications. She started by way of an English Philosophy and Creative Writing Degree from Brandeis and dreamt of a future in editorial writing. However, a chance interview steered her in another direction and she never looked back. Since then, for better or worse (and we’ll say better), she’s had a host of publishing and PR jobs, including becoming the first Social Media Manager for ELLE. Through the challenges of being on the forefront of social and having to continually prove herself as a worthy seat at the table, Lindsay has certainly triumphed and has invaluable advice to share with the very much lagging industry. After all, it’s this insight and being headstrong that brought her to her current role as VP of Communications at Casper, a sleep startup. We learned so much from our conversation with Lindsay and hope you do too. For more from her, check out @lindsaykap and @Casper.