As the startup world continues to expand, with it the myriad opportunities and options for success do as well; and no one process suits everyone. As a partner at preeminent VC firm Union Square Ventures, Albert Wenger navigates that everyday, and as a failed entrepreneur, it’s something he’s experienced even more personally. A self-described technology optimist, takes us through the approach he and his partners take to investing and advising companies, how, as a company, they aim to be effective and not “right,” and why staying focused on a single (evolving) thesis has lead to their success. What You’ll Learn: Why as a founder one of the biggest mistakes you can make is hiring people like you. How raising money is like singing in the shower (and why that matters). How deferring funds early on is a better path to success. What will upstage capital as the new most important commodity in business. Why all software can and should be social at its core.

As interconnectivity of the world increases, so does the call for authenticity and two-way, flexible, communication. Brands who once dominated the marketing conversations are now struggling to find meaningful ways to engage with their customers, companies large and small who once offered canned benefit packages are struggling to relate to and support their employees. Meghan Graham first became aware of this phenomena in a meta-scenario as she was reporting on the decline of advertising dollars to publishers as a writer for Wired; however, since then the writing on the wall has only become more clear. Seizing the opportunity to modernize the way we engage with people (customers, coworkers, parents, or all three) on a personal level, she founded Brick Wall media, which is not only guiding brands to be more impactful, but setting the example for companies to do that as well. What You’ll Learn: Why sharing values with your customers and employees is table stakes for remaining relevant. How flexible hours may be the solution to long-term satisfaction and productivity. How larger brands need to evolve their thinking around what it means to connect with their customers through truly useful content.

Tony Hendra is, without question, one of comedy’s living legends. Described by the Independent of London as “one of the most brilliant comic talents of the post-war period,” Tony boasts a career including being one of the original editors of the National Lampoon magazine, discovering some of the original members of Saturday Night Live, and as one of the stars of the rockumentary This Is Spinal Tap. Over champagne at this Upper West Side apartment, he discusses how the industry and art has changed over time, particularly as it’s adapted for new media, how he’s adapted to that with his podcast the Final Edition Comedy Hour, and his stance that no two vessels deliver the punch line the same. What You’ll Learn: Why you shouldn’t chase trends and why media matters. The parallels of satirists and monks. How brands can rise & fall depending on vision and leadership. Check out some of Tony’s latest work as founder of the Latest Edition Comedy Hour: https://soundcloud.com/thefinaledition

One of the paramount needs of an industry so dependent on innovation as tech is the ability to understand varied perspectives and experiences; and yet still, the issue of diversity, specifically gender representation, is longstanding. It’s an issue that, over the course of her career, Rachel Sklar has not been able to ignore. Starting off as a lawyer in New York City, it became clear to her that she was perhaps an outsider in the boys club. However, it was when she transitioned to a stint in the early days at the Huffington Post, fighting tooth and nail to create opportunities for herself and ultimately getting access and insight into other industries, that the “where are the women?” drumbeat was evident in every single one. Over Cole del sole prosecco provided by Alphabet City Wine Company, she talks about her outspoken nature on the issue of gender politics and her efforts in advancing the conversation through founding both The List and Change the Ratio. What You’ll Learn: The parallels of founding a startup and early parenthood. How being hungry and creating opportunities is still the norm for women in modern industries. How tech is no longer an industry on its own, but rather, sits at the center of the venn diagram that is business. Why it’s important to say you’re an expert and mean it.

With exponential growth in innovation and tech, the world around it has shifted, leaving opportunity for new jobs and new fields that never existed before; it’s a sector that was created by a generation of makers who saw the early days of the internet not for what they were, but what they could be. Avi Flombaum is one such maker. As a kid growing up in the early nineties in New York City, Avi was introduced to the internet by way of occupying his time in a computer lab while his mother tutored and it was then a passion was forged. A passion that would sustain him down a path of self-taught development skills, foregoing a formal college degree, but opening the door to a successful career in tech, and ultimately founding the Flatiron School. His vision is clear: to shepherd students like him, with a passion for technology and a desire to help shape its future, to have access to a curriculum that he could only dream to have as an adolescent and to give them the chance to change their lives. What You’ll Learn: How vocational schools can get you to your desired goal, but is not a shortcut. The importance of a well-rounded educational experience. How growing up in tech has changed in two decades and the opportunities created from it.

By her resume alone, it’s no surprise that Jessica Beck is a successful startup founder: from her roots at Harvard Business School and experience at McKinsey, she has been brought up with a sustainable business acumen. However, as she describes over a bevvy of micro IPAs, this sort of formal training can only take you so far. There was a lot she had to learn on the job  when creating her product, Alfred, which bridges the service industry with the on-demand expectation of users by providing the everyday person with a personal assistant, or “Alfred,” to help with their intimate daily tasks (think: errands, shopping, laundry) … without them ever actually meeting. What You’ll Learn: As a founder, knowing when you should ask for help (in both funding and roles) The benefit of knowing how to do every job in your company How a lightweight, non-digital version of your product is the best proof of concept

Online dating is a crowded space and becoming increasingly so across platforms. Seemingly a new phenomenon over the past few years, this extreme growth could be attributed to a time in 2011 when, within two weeks of each other, Tinder and Hinge launched and changed the game as we knew it. Hinge’s founder, Justin McLeod, had been working on the app for two years, pushing off a start date at McKinsey until he finally decided to make the app his full-time job. Over grapefruit La Croix, Justin discusses the evolution of the online dating space and how to differentiate in such a saturated industry. What You’ll Learn: The data showing difference in gender behaviors on dating apps and the impact on the products Where and when the content of a dating profile matters How to approach launching a product that requires people to be on it for true success Defining success from a business perspective and the surprising front runners in the industry

One of the most important and valuable commodities in the digital world is data. However, accessing and harnessing this powerful resource can be intimidating; that’s where Hilary Mason and her team at Fast Forward Labs step in with their goal to demystify these complexities and instill confidence in their clients. As a computer scientist, Hilary has spent her career fascinated how by how she can use her programming skills, deductive reasoning, and strategic thinking to help create new, useful, and often necessary digital products. Over crisp apple cider, she discusses her experience as the chief scientist at Bit.ly and how that lead to her deciding to create her own thing. WHAT YOU’LL LEARN The tenets of what makes a great computer scientist How computer science (and it’s subset data science) is completely accessible Why data can hold the secrets to everything you need to know about your product or audience

The world of venture capital in New York City tech has changed significantly in the past decade with access to investment for early stage companies becoming more and more challenging. Enter Notation Capital and it’s co-founder, Nick Chirls, who believes that there’s a gap for seed stage investments that he and his team intend to fill. And Nick knows the NY Tech scene. Over beers provided by Alphabet City Beer Company, he walked through his disgust with the traditional finance world and why he left it to explore the startup world, ultimately landing as a the head of investments at BetaWorks. What You’ll Learn How investors choose their first investments The importance of sticking to your thesis as a VC How the evolution of older, larger funds has hurt early stage tech companies The challenges of being in an equal partnership

As we’ve learned, there is no clear path to successful entrepreneurship and Alanna Gregory’s story is a shining example of that. With an engineering background and beginnings in the world of finance, she was unexpectedly struck with inspiration. Now, as the co-founder of Vive, an on-demand blowout scheduling app for women in metropolitan areas, she’s had to continue to make a lot of risky decisions in order to grow and pivot her business. Over pinot noir, generously provided by Alphabet City Wine Company, she talks to us about the importance of assessing the data at every turn, but that ultimately your passion for your company is paramount to your success. What you’ll learn: - Sometimes data doesn’t tell the whole story - How pivoting in life and in your company can be a saving grace - Why the motivation of founding a company should be more than big business - Why it’s important to put something out there, even if it’s not 100%