Mark Smukler is an investment banker turned software engineer turned PropTech entrepreneur who spent the last 5 years building technology that elevates apartment living. In 2016 Mark founded Bixby, an app to help property managers streamline operations and provide a better resident experience. Mark sold Bixby to Hello Alfred in 2019 where he's spent the last two years leading product development. Today Mark is working on a new startup yet to launch called Flow that provides consumers on-demand access to nearby location-based businesses such as co-working spaces and gyms that would otherwise require a membership or long-term commitment.

-On the influences of an international childhood

-From investment bank in Little Rock to entrepreneur co-founding Bixby

-Pioneer of PropTech: Why is real estate so behind as an industry?

-The rollercoaster life of a founder (no fundraising = not even ramen!)

-Leading Bixby to acquisition by Hello Alfred (+ the transition to running a department within a larger company)

-Advice: Seek help! Most of the time, all of you have to do is ask.

-"I am incredibly bullish on New York and incredibly grateful for New York"

-NEW STARTUP ANNOUNCEMENT: Flow!

Alex Ferber is a co-founder and partner at Green Egg Ventures, an early stage venture fund investing in software startups that are solving problems for businesses. Prior to co-founding Green Egg Ventures, Alex worked at Metamorphic Ventures.

-How he got into venture capital (luck!) when his goal was to work in a startup

-On imposter syndrome as an investor

-The invaluable experience of working in his father's business, HoMedics + risk tolerance with a safety net

-The butterfly effect / putting yourself out there

-Finding your own flavor of due diligence

-Building a new fund is building a startup

-Functions of a junior VC role

-No magic behind the curtain: the four questions they answer

-Lasting trends from the pandemic

-How does someone get "good" at VC? It's not black and white.

-Unique traits of New York's startup ecosystem

Jessica Li is the 2nd growth marketing hire at Series C, General Catalyst backed Zageno, the B2B procurement marketplace for the life sciences. She also heads content for Elpha (Y Combinator S19, community of 35K+ women in tech), Harvard in Tech, and Techstars Boston.

She previously worked in venture capital at Soma Capital (employee #1), General Catalyst, Romulus Capital, Global Founders Capital, and Female Founders Fund; in growth and operations at Morning Brew (acquired by Business Insider) and Luxe (Google Ventures backed and acquired by Volvo); in investment banking at Morgan Stanley; and in public markets at Northwestern Mutual and a family office. She graduated from Harvard with high honors in applied math, computer science, and economics, where her thesis research was completed with the 2016 Nobel Laureate in economics, Oliver Hart. She has worked with startups in MassChallenge, Techstars, Alchemist, Envision, Zane, and other programs.

-How Jessica's resume is so long despite being in her early twenties!

-The impact of immigrating from China to the US at age 10

-Does a Harvard degree derisk its holder? 

-Thriving on "productive procrastination"

-The "touch it once" mentality

-How she broke into VC (hints: be helpful to people + identify your superpower) and why she left it

-Zageno: What is it? Why did she move there on the operational side?

-Does being an operator help one to be a better investor?

-"Don't worry about disappointing other people"

Sam Bobley is Co-founder and CEO of Ocrolus, a fintech infrastructure company that powers underwriting processes for lenders like SoFi, Lending Club, and Enova.

He started building Ocrolus in his parent’s kitchen when he was 22-years-old. Six years later, the company has more than 900 employees globally, across four offices. Along the way, Sam authored a patent application, helped raise over $50 million in venture capital, and surrounded himself with a world-class team of coworkers, investors, and advisors. Inc. Magazine recognized Ocrolus as the #1 fastest-growing fintech company nationwide, and the #1 fastest-growing software company in NY.


-How the idea was conceived

-Pressures of being a young CEO

-Raising money on just an idea

-Unique AI: "Human in the Loop"

-Fundraising: Blessing & Curse

-Selling into first customers

-Hiring: Domain vs. Stage Expertise

-Mentorship is critical

Ryan Freedman is the founding general partner of Alpaca VC (formerly known as Corigin Ventures), a New York based seed firm that leads rounds across sectors. Ryan is an entrepreneur turned investor, from Coral Capital (tech enabled commercial finance operation) to Corigin (private real estate investment firm and early pioneer of co-living) to the leading VC that Alpaca is today.

Ryan shares notes on:

-The story of his impressive career to date, launched on a handshake!

-Differences between real estate and venture capital

-The rebrand from Corigin Ventures to Alpaca VC

-Transparency through marketing, including the firm's 19 factor scorecard

-Identifying risks early to pick 8-10 investments from 1,500+ opportunities

-Future of New York as a tech scene

-Diversity: LPs finally paying attention + personal commitments by the Alpaca GPs

-Why founding teams are so important

Charlie O'Donnell is the sole partner and founder of Brooklyn Bridge Ventures, a very well known VC and the first in Brooklyn, which invests in New York based startups at the seed and pre-seed rounds (first $750k). With nearly twenty years of experience in the industry (Union Square Ventures, First Round Capital, and the GM pension fund), Charlie shares key insights around startup investing.

-"Portfolio Thinker" vs. individual deal focus

-Why "great team" is thrown around too much

-Is diligence a waste of time?

-The problem with angel investing

-2020: Year of the Twitter DM Pitch!

-New York Bullshit

Hadley is a founding general partner at Eniac Ventures, a legendary seed stage VC in New York City. He's held operational roles in engineering, product management, and strategy, was an early employee at Vlingo, and served as the CBO at Thumb.

-Founder friendliness as a secret sauce

-Learning VC on the job as a GP

-The benefits of Eniac's diverse team

-The future of venture capital

Rachel Lauren is a venture capital analyst at BDMI (corporate venture arm of Bertelsmann) with a great story.

-How she broke into venture capital (twice!)

-Why you shouldn't invest more than you can afford into your uncle's startup

-Diversity initiatives in the startup ecosystem

-New York vs Silicon Valley (hint: one is more pretentious)

Gil Eyal is the founder of HYPR (rated #1 Influencer Marketing Platform), acquired by Juliusworks in 2020. He now serves as the Strategic Advisor to the Chief Innovation Officer at Silverstein Properties, is a startup mentor at Techstars and Sapir Venture Partners, and has a unique initiative in the works at Starfund.io. Gil speaks openly with Zach about the highs and lows of being an entrepreneur.

Chinedu Echeruo is a visionary entrepreneur in New York City. He's the founder of HopStop (acquired by Apple), Tripology (acquired by Rand McNally), MindMeet, Love & Magic, and the Startup School of Alchemy. Listen and learn the science behind entrepreneurship.