Gab Saper is a personal stylist and founder of Wardrobe Editor™️, who helps you uncover the coolest, hottest, best version of yourself through what you’re putting on your body. She’s part stylist, part emotional translator—known for helping clients untangle the mess of “shoulds” in their closet and figure out what actually feels good again.

Drawing on her experiences from fashion school and working in retail, media and tech; she brings an intuitive-meets-practical approach to style that works as hard as you do.

Gab guides you to dress in a way that commands respect at work, turns every head at the restaurant and makes you the envy of every mom (or aunt!) on the playground – without sacrificing comfort or utility.

One of the primary ways she does this is by flipping typical style advice on its head. She’ll never advise you to keep up with the trends and she believes deeply that horizontal stripes are for everyone. Her process isn’t about perfection—it’s about building a wardrobe that saves you time, reflects who you actually are and feels damn good to wear.

Gab lives in Greenwich Village with her husband and children…and by children, she means handbags. Some of her favorite things include an empty inbox, spicy margaritas and laughing out loud to a podcast. She was once featured in The New York Times for her very tiny, very organized apartment—proof that she lives what she teaches: edit ruthlessly, wear joyfully.

During this episode, we discuss:

• What Gab does as a personal stylist, working with many women in tech
• How a wardrobe should support your life
• What inspired Gab to leave her tech career and pursue her styling business
• Advice for what people who are newer to tech should wear to a job interview
• How to determine the balance between being too fancy and too casual
• What to wear if you work remotely
• Suggestions for what to wear to networking events
• How to dress for conferences, especially as a speaker
• Gab’s top product recommendations
• Why you should wear clothes that make you feel like yourself
• How to dress when you get into a leadership role
• Advice for anyone who would like to pursue a career in styling
• Her shoutout to Nove

And more. Tune into this episode as we dive into all things styling in tech!

Andrew Ackerman is a VC, angel investor, SPV syndicate sponsor, and former entrepreneur with over a decade of startup investing experience and 70+ early-stage deals. A former generalist who later specialized in EdTech and now focuses on PropTech and Construction Tech, Andrew has built a reputation for turning networks into true platforms.

At Dreamit, he launched industry verticals and co-created the Customer Sprint and Investor Sprint programs, connecting founders with hundreds of investors and enterprise partners — and helping them raise capital and close deals faster through structured processes instead of one-off introductions.

Beyond venture, Andrew advises corporate innovation teams, CVCs, developers, general contractors, and landlords on designing high-impact venture structures. He’s also a prolific contributor with 60+ published articles in outlets like Fortune, Forbes, Propmodo, BUILDER Online, and Edsurge, and is a frequent speaker and panelist at conferences across the U.S. and globally.

During this episode, we discuss:

• How Andrew did consulting for a few years before spending 8 years building a startup
• Why the best startups want to be with the best investors and vice versa
• How he got started as an angel investor
• What it was like to jump from small angel investing to large amount of applicants for accelerator
• Investing in husband and wife teams before and why many VCs don’t do it
• What made him want to specialize in ed tech then later proptech and construction tech
• How he got the inspiration to write his book

And more. Tune into this episode as we dive into all things investing!

James He is the co-founder and CEO of Artificial Societies, a company at the forefront of simulating human social dynamics using AI. With a background spanning data science, behavioral sciences, and entrepreneurship, James has dedicated his career to bridging technology and human understanding.

After earning First Class Honours in Psychological & Behavioural Sciences from the University of Cambridge, where he focused on data science, neuroscience, and social dynamics, James gained experience as the first machine learning and data scientist at Yonder Credit Card. There, he developed and deployed advanced systems for behavioral prediction and decision-making.

At Artificial Societies, James leads a team building AI-driven simulations that allow organizations to test messages, products, and policies within realistic, organic digital societies before launching them in the real world. The platform creates hundreds of unique AI personas that interact and form communities, enabling clients to gain actionable insights into persuasiveness, message spread, and audience response at scale. Under his leadership, Artificial Societies has delivered over 25,000 insight reports and is partnered with leading brands and research institutions.

Driven by a vision to transform how organizations understand and engage with their audiences, James is advancing the use of artificial societies as a new paradigm in market research and social analysis.

During this episode, we discuss:

• How James left home when he was 14 to go to New Zealand for school on his own
• His interest being at the intersection of understanding humans and technology
• What Artificial Societies is
• How customers use Artificial Societies
• The importance of partnerships with like-minded companies
• How he uses Artificial Societies for itself
• His shoutout to Matt Carey, who runs AI Demo Days in London

And more. Tune into this episode as we dive into the intersection of AI and humans!

Bethany Fiocchi Root is a results-obsessed marketer with 17+ years of experience helping high-growth companies scale smarter and faster. As Founder & CEO of Oceanview Marketing, she works with startups to design and execute strategic marketing programs that match the stage they’re in (and the growth they’re after).

Over the course of my career, Bethany has grown multi-million dollar marketing programs and managed millions in ad spend across both scrappy startups and well-known brands like GoDaddy and Bluehost.

During this episode, we discuss:

• How Bethany helps startups move their marketing forward
• The importance of getting a product market fit
• Why you need to know your goals and objectives at the stage you’re at
• Bethany’s background in startups
• How to nail your messaging and positioning by doing market research
• Why cost of customer acquisition is a big metric to look at
• The importance of being patient when trying new strategies
• How to focus on a founder personal brand
• What AI can and can’t be used for in marketing
• The benefit of storytelling in your marketing
• Her shoutout to Startup Boston

And more. Tune into this episode as we dive into all things marketing!

George Damouny, Venture Partner at Plug and Play, has a diverse background of finding startups to operational roles, before applying his experience to investing in venture capital early 2014. Since then, George has led venture deals in over 200 startups, primarily in retail, financial services and sustainability.

Some of his deals include Honey (acq. by Paypal for $4B), Kustomer (acq. by Meta for $1B+), Rappi ($5B+ val.), BlockDaemon ($3.25B+ Val.), Flutterwave ($3.25B+ Val.), BigID ($1B+ Val.), Turing ($1B+ Val.), Esusu ($1B+ Val.), Manscaped, Power (acq. by Marqueta), Even Financial (acq. by MoneyLion), Airkit (acq. by Salesforce), Stellar, Onfido, PayActiv, Madison Reed, Albert, Naadam, Symend, Oxio, Railz, Zama, Gr4vy, Heirloom, and many more.

George holds a B.A. in Behavioral Science with a Minor in Communications in the information age from San Jose State University, where he graduated with both the President's and Dean's Honors Awards.

During this episode, we discuss:

• How George joined Plug and Play very early, when it had less than 20 employees, and now there are nearly 800
• His past experience founding a company in the B2C space before running a medical facility
• How venture capital fell into his lap
• Being a generalist before specializing
• His favorite deals he’s been a part of
• The importance of learning from mistakes and having the opportunity to invest
• Why it’s crucial to understand founder dynamics
• The combination of the right market, right team, and right product
• Popular sectors in tech right now
• His shoutout to Salil Deshpande of Uncorrelated Ventures

And more. Tune into this episode as we dive into all things VC and great deals!

Rebecca Lyons is the founder and CEO of HerSay, an AI-powered doctor visit companion that helps women advocate for their health with clarity and confidence. After her own journey with medical gaslighting and a delayed diagnosis of stage 4 endometriosis, Rebecca turned pain into purpose—building a tool that empowers women before, during, and after every appointment.

A seasoned sales and strategy leader turned tech founder, Rebecca blends over a decade of experience in operations, consulting, and digital transformation with a bold, mission-driven approach to femtech.

During this episode, we discuss:

• Noticing her first symptoms of endometriosis about 8 years ago but her results came back as “normal” so her doctor was dismissive about it
• How the diagnosis became a very empowering experience
• What she found with women who were navigating the medical system were likely less heard and experiencing medical gaslighting
• How she used a series of Meta Ads to publish hypothetized problem statements
• Her process for working with a no-code tool to build the app to create a prototype and then brought it to a developer
• Doing a soft launch/beta with small cohorts
• Her advice for knowing which feedback is worth implementing or not
• How she works through compliance and the regulatory landscape
• What she wishes she knew earlier on in her founder journey
• Her shoutouts to Megan Kane of Rellia and Argentina Beltran of InclusifAI

And more. Tune into this episode as we dive into all things women’s health!

Shane Lykins is a founder and product builder based in San Francisco, exploring the intersection of AI and marketplaces. He’s worked on product and growth across some of tech’s most recognizable names, including Airbnb, Pinterest, and Outdoorsy. Today, Shane focuses on building AI-powered micro-SaaS tools and launching fast, scrappy experiments that solve real problems for startups. Whether he’s advising early-stage teams or spinning up his own ventures, Shane brings a builder’s mindset, a founder’s urgency, and a curiosity for what’s next.

During this episode, we discuss:

• His grandfather’s business that planted the entrepreneurial bug in him
• Shane’s interest in computers at a very young age
• How he lived in Austin and worked as a flight instructor until he decided to move to San Francisco and work in tech
• His career at Airbnb, Outdoorsy, and Pinterest
• What led him to starting his own business
• The company he founded and shut down
• What makes a great product and why startups should embrace AI
• All of the projects he’s built and launched lately
• How to know which ideas are worth chasing
• His shoutouts to Collin Gardner of Yonder Ventures & Clif Claycomb of Longtail

And more. Tune into this episode as we dive into all things vibe coding and product!

Kendall Crocker is a fractional COO and strategic advisor with a 15-year track record across venture capital, startups, and strategy consulting. She works with early-stage founders at Seed to Series B to help them scale faster and punch above their weight in fundraising and execution. Most recently, Kendall was a Partner at a global early-stage VC fund, leading deal execution across six countries, with board roles in three. Before that, she was the first VP of Operations at a Series B startup, where she helped scale the company to a $50M Series C. She launched her career in strategy consulting with Monitor Deloitte, leading large-scale transformation and customer experience work for clients from Exxon Mobil to Tiffany & Co. Kendall brings a combination of operator intuition and analytical rigor to the organizations she supports. Outside of work, you can find her cycling, meditating (certified mindfulness instructor), traveling (40 countries), or up early with her toddler.

During this episode, we discuss:

• How Kendall started in a corporate environment doing strategy consulting, working with Fortune 50 clients, before leaving to launch an innovation function for Fortune 100
• Why she decided to go into startups in her early 30s and how she jumped in with both feet
• Getting her first startup job by meeting a founder for coffee, staying for three hours, and immediately getting an offer letter
• Why she transitioned into a career as a VC
• Advice for if you’re getting into VC “later” in your career
• The importance of building a community
• Why you need to prioritize leveraging your personal brand
• How she switched gears to becoming a fractional COO, now known as the “Fundraising Sherpa”
• Her advice for any founder who realizes they waited until it’s too late to get help with operations and fundraising
• The importance of paying attention to founder mental health
• Why you should take more risks in your career
• Her shoutouts to Unlock VC by Sophie Winwood, The Helm, Dream Ventures, and Golden Hour Ventures

And more. Tune into this episode as we dive into taking leaps in your career and trying something new!

Zinnie Zhang is a 25-year old pioneering founder and CEO of Enttor, an AI-native marketing platform that empowers enterprise teams to scale authentic content creation and workflow efficiency. A Vanderbilt Computer Science graduate, she made the bold decision to leave Harvard Law School in her first year to pursue her vision of transforming the marketing stack through generative AI. With a deep understanding of tech and strategy – honed during her tenure at Yext – Zinnie led her team from dorm room to real-world impact, signing a major enterprise contract, raising pre-seed funding from MaC Venture Capital, a16z scouts and Knot API’s CTO as well as gaining advisory guidance from tech luminaries like Kieran O’Reilly and Nicholas S. Zeppos. Zinnie is passionate about building a future where AI amplifies human creativity. She advocates for women in tech and AI leadership, and regularly speaks on the intersection of AI, enterprise software, and diversity.

During this episode, we discuss:

• How she previously worked for an enterprise marketing software company and noticed inefficiencies that led her to building Enttor
• Where she’s failed and how she’s bounced back after failure
• “No” isn’t forever
• The importance of building in public
• How to be flexible and hold accountability as a founder
• What nudged her to leave Harvard and continue building Enttor instead
• Her advice for young founders
• What founders who are building with AI should know
• Her shoutout to Anna Monaco of Paradigm

And more. Tune into this episode as we dive into all things being a young founder!

Ashley DiBiase is the founder of Tech Startup Network, an integrated platform built to provide direct pathways to essential resources for founders, VCs, employees, and consultants.

She also owns Dash of Social, a content marketing agency specializing in social media management, blog content, and email marketing. Working closely with their clients, Ashley and her team help small businesses and tech startups craft and execute value-driven marketing strategies designed to establish thought leadership, grow online communities, and drive brand awareness.

Additionally, Ashley founded Massachusetts Business Network in 2022, which is the only statewide publication that provides free to low cost resources that support organizations with increasing their visibility and establishing thought leadership through its podcast, blog, and directory.

Ashley is a graduate of Stonehill College, where she received her Bachelor's Degree in Business Administration with a concentration in Marketing. She is a TEDx speaker, has been named a 40 Under 40 Honoree by Cape & Plymouth Business Media, and was recognized as Best Social Media Specialist by Boston Business Women.

Ashley currently serves as a Board Member for the Brockton Visiting Nurse Association (BVNA) and Middleboro Public Library. When she isn't working, you can find her running on her Peloton or curled up on the couch with a book.

During this episode, she discusses:

• What Tech Startup Network is
• Her reason for starting it
• What her background in marketing and community building is
• How people can benefit from Tech Startup Network

And more. Tune into this episode as we dive into all things Tech Startup Network!