Last week we met with Steve Martocci and heard about the challenges of being a first time founder in the early stages of a tech startup. This week, he continues his story (as he and Dan finish the bottle Angel’s Envy bourbon) about the evolution of GroupMe from $850K to $10MM and what that growth meant. This is when it gets real.   He walks us through their growth, utilizing groundbreaking PR tactics at SXSW, to raising vs. partnership conversations with major players in the space, and finally becoming one of New York tech’s biggest exits to-date (and life beyond that acquisition). Steve’s candid account offers invaluable advice for investors and founders alike, and moreover, insight into the very nuanced and complicated realm of the startup world. (We’ll drink to that.) For more from Steve, holler @smart and see his newest product Splice.

Steve Martocci is the co-founder of Splice, a technology platform for music creators which streamlines the fragmented process of creating and sharing music, freeing musicians to spend their time and energy on the creative process. Previously he was a co-founder of GroupMe, a group messaging service that in August 2011 was acquired by Skype, which was subsequently acquired by Microsoft in October 2011. Prior to GroupMe, Steve was a lead software engineer at Gilt Groupe and founded Sympact Technologies and Bandwith.us. However, it was over Angel’s Envy bourbon that we learned that Steve’s success can really be attributed to the breakup of Phish. Of course, he had all of the accolades to garner a successful career, Steve graduated from Carnegie Mellon University in 2004 with a B.S. in Information Systems, and has had a string of high profile tech jobs with amazing collaborators which give him his business-savvy and tech know-how. However, it was his love of music that has motivated him and remains a constant thread across his  career. In part one of our (first ever!) two-part story we learn a lot about those early days in his career and the catalysts that set his trajectory toward the tech superstar we know today.

It’s said that true innovation is the reduction of complexity, and if that’s the case, Naama Bloom is an innovator amongst innovators. Most recently acclaimed as the woman who brought the period to virality status, she has made a business of taking the often overly complex conversations of women’s health and milestone moments (which were reserved for whispers or clinical jargon) to the tens of millions of views on YouTube and furthering it to content and newsletters via her company HelloFlo. However, while demystifying these conversations amongst women seems like a “no brainer,” it is not without a sharp strategic mind and business savvy that it has been executed. As a tech vet, for better or worse earning her nickname as “the Closer,” Naama spent majority of her early days jumping from digital company to digital agency and over again as they folded in the early nineties, which inspired her to eventually go to Cornell Business School. Upon completion, she emerged with more solid footing in the business world and began to climb the ranks as a marketing executive at both American Express and Harvest before she was inspired to take on founder life full-time. Over a bottle (or two) of red Zinfandel from Sonoma County, Naama shared her experiences of starting a company with just a great idea and great chutzpah, the importance of choosing a cofounder with complementary skills, and the painful battle of raising money while trying to build a brand (and the battle of maintaining a two founder household with her husband, David Bloom). True to her nature as an innovator, she tells her story without euphemism or pleasantries and for that and more, she is truly commendable. For more from Naama, she tweets as @NaamaBloom and be sure to check out Camp Gyno and First Moon Party on YouTube.

We at SIAB call Gene DeRose the “O.G. of the New York Tech Scene.” In his 25 year career here, he’s surely seen and been a part of his fair share of the evolution of the industry. Hailing from Westchester and going to school in Virginia, he landed back in NYC originally in the pursuit of journalism. However, as the tides shifted, he steered a new course (well, with a brief stint as a bartender) and became the co-founder of Jupiter Communications; taking it from a newsletter to the media success it became, and then taking it public. Beyond that, he’s consulted and founded a number of interesting projects, harnessing digital-virtual power and bringing it back to the real world with both Mouse and House Party. Gene joined us for Herradura Añejo on the rocks (with a little lime) and bestowed his saga; from those early journalistic experiences, surviving the “digital winter” of the mid 2000’s, taking a company public (and maybe not doing it soon enough), making good and bad investments, and the “borderless internet” he’s working towards now. Gene’s is a true founder’s story and we can all take a page from his experience. You can find Gene on Twitter @genederose.

Kristen Hawley has one of the most diverse and inspirational stories we’ve heard to date. With a journalism degree, background in media, love of epicurean culture and experience dabbling in the tech world, she’s created a path for herself which only begins at the intersection of these things. However, her agility and strategic perspective has lead her to create Chefs + Tech, offering an interesting and unique spotlight on the emerging technology trends in the culinary world.   Kristen has certainly earned her chops along the way by navigating various industries and cities; circumventing the treacherous publishing and media world at Hearst in New York City and skimming the tech scene at PopSugar and Twitter in San Francisco, she ultimately decided to combine the two things she’s most passionate about - food and media - to create her ideal job. Her story encourages us to follow our gut and remain adaptable, and do not be fooled. What she calls “luck,” is really her tenacity to adapt quickly and to create the next best opportunity (when it otherwise doesn’t exist).   Oh, and she changed our minds about Pinot Noir, as well! Get in on the latest on Chefs + Tech here. And more from Kristen: @kh.

This week's episode features our friend Soraya Darabi, the co-founder of Zady. Zady is the online destination for conscious consumers. They source and sell and make stylish apparel for men and women, and detail the stories and origins of the items produced. Much more than a fashion startup, her company is a brand and a movement towards responsible manufacturing, global sustainability, and human rights in the apparel industry.   However, before that, we follow her journey from working as a College Marketing Rep for Sony Music, to jobs in media, both bringing journalists at The Washington Post into the digital present and discovering the NYC tech world while at Conde Nast & The New York Times. Ultimately, she found her way to become an entrepreneur at startups like drop.io, foodspotting and now Zady. Her path is in no way ordinary and extends beyond the “tech socialite” description she’s been ascribed. Oh, and she also offers up the secret to a mean mango mimosa. Hit her up with follow up questions at @SorayaDarabi.

Rex Sorgatz is a jack-of-all-trades; self-described as a media collector, product strategist, creative technologist, culture hacker, writer, designer, advisor, and consultant, but who is currently spending his time as the Founder & Partner of Kinda Sorta Media.   He joined us for homemade cider, which he made and provided (a SIAB first), and told us about his very fascinating path; from starting as a Pultizer-prize winning journalist in North Dakota to working at a print magazine ABOUT the internet (yes, this is a thing), and how he became @fimoculous. From there, he’s made his way through different parts of the digital industry, with “view source and hack it backwards” beginnings, and offers a unique point of view because of it. At the end of the day, Rex is fighting the good fight to find the balance between being an expert or generalist (and probably both). Rex’s musings can be found here and he also contributes to a Medium group dubbed the Message.

Christina Mercando is the founder of Ringly, a wearable technology company based in Brooklyn, New York which launched in June of this year. However, with 10+ years in the technology industry, Christina has taken quite the interesting path to get here.   She joined us for sparkling wine and shared her early experiences in tech; helping her dad manufacture medical CD roms in their home in Irving, New York and her days working through video projects at HCI at Carnegie Mellon. Christina ultimately found her way into the professional realm working in the music marketing industry and finally doing user experience and design at Hunch, which was later acquired by Ebay.   However, Christina always had the ambition to do her own thing. Now, with Ringly, she’s able to take the lessons she’s learned in working in both large- and small-scale companies and continue to evolve with the future of technology. To other entrepreneurs: “take a risk if you can.” To hear more from Christina, follow @jetpea on Twitter.

Tom Clifton is co-founder and head of B2B at Animoto, a subscription-based web and mobile platform that enables businesses and consumers to create dynamic, professional videos. Launched in 2007, Animoto has grown through several rounds of funding to over 10 million users and has won every major industry award, including two Webbys, a Crunchie, and a SXSW Interactive Award, as well as being chosen as Crain's Top 25 Best Places to Work in New York City.   However, getting to this point has not been without its many steps; Tom joined us for Negronis and told his story -- his tech beginnings as a 12 year old in Seattle pitching & building websites with his brother, an academic career including bible, computer science & music schools, and ultimately co-founding Animoto with a group of entrepreneur friends. All the while learning that building and working with a great team in order to make a great product is one of the keys to finding balance as an innovator. For more on what Tom’s up to, check out @Animoto.

Amanda Peyton is the co-founder of Grand St., a marketplace for creative technology that was recently acquired by Etsy. Peyton is a technologist at heart and has worked at the intersection of technology and design for her entire career. She is an alum of MIT Sloan, Northwestern & Y Combinator and currently lives in New York City. But that’s just scratching the surface.   Amanda “classed it up” with Bulleit Rye on the rocks and shared her beginnings as the “5th grader with the side hustle,” living in China, becoming the “queen of the geeks” in Texas, and ultimately her three-startup-strong experience. All the while maintaining a DIY, entrepreneurial spirit and embracing the mess of the startup world by seizing the opportunities it has to offer. Her story is certainly as bold and strong as her drink of choice - cheers! You can check out more of her musings on the internet via @amandapey.