Worth

As a reporter at TechCrunch, Natasha Mascarenhas writes about early stage startups. She joined us to talk the future of media and higher education, asking more thoughtful questions, and telling better stories.

It's always fun to talk to people who love what they do, but are also much more than their work. Enjoy!

[2:43]: A day in the life of a TechCrunch reporter

[5:00]: Her focus on edtech and predictions about the space

[7:54]: Chasing down her dream of writing professionally

[11:45]: How to uncover interesting stories and listen better

[17:11]: Thinking through her own content consumption as a creative

[20:37]: Substack and the future of media

[25:55]: Favorite books

Charlie Feng is the Co-Founder of Clearbanc, the fastest, most affordable way for founders to fund their business and the biggest investor of eCommerce businesses in the world.

Previously, he spent time founding companies in the chatbot and marketing automation space, and even had a short stint as a professional gamer.

In this conversation, he and Asher discuss some of the metrics that Clearbanc's algorithm leans on when determining whether or not to fund a business, lessons learned from building Hemingly - Charlie's first company, and the constant pursuit of adding leverage to the human experience.

[1:04]: Pro gaming and carryover into the world of business

[3:27]: Charlie's first company and why founders need to set a closing date when fundraising

[5:36]: Customers don't know what they want until you actually put it in front of them

[6:59]: The insight that lead to Clearbanc

[9:47]: How Clearbanc helps founders fund their businesses without giving up equity

[13:21]: The metrics Clearbanc looks for when deciding whether or not to invest in a company

[16:01]: Playbook for founders on navigating COVID-19 and the launch of Clearbanc Runway

[20:28]: The Condor and the Bicycle and adding leverage to human beings

Stephanie Bowker is the Head of Marketing at Spendesk, one of the fastest growing Fintech startups in all of Europe.

Previously, she was the first Product Marketer at Gusto and during her time at Intuit, had the opportunity to work closely with Co-Founder Scott Cook.

In this conversation, we talk first principles of effective marketing, how to divide up responsibilities as your team begins to grow, and Stephanie's journey from the Bay Area all the way to Paris, France.

[1:11]: Getting a crash course in Product Marketing & Product Management at Intuit

[3:34]: Learning a customer first approach from Intuit Co-Founder Scott Cook

[4:41]: Joining Gusto to build the company's Product Marketing team from the ground up

[6:53]: Stephanie's advice for product marketers on how to narrow down your target audience

[8:32]: Moving to Paris and joining one of Europe's fastest growing Fintech startups in Spendesk

[10:05]: Scaling Spendesk and matching the marketing team to the funnel

[14:40]: First principles of effective product marketing

[17:46]: Stephanie's favorite books and podcasts

Erika Hairston and Arnelle Ansong are the co-founders of Edlyft (YC W20). While they pieced together their own support systems as CS majors, they're building Edlyft to provide structured mentorship for aspiring engineers, at scale.

On who gets to start a startup, betting on people of different backgrounds, and more.

[2:13]: Leaving jobs at Bain and LinkedIn to go full-time on Edlyft

[14:44]: The 'hair on fire' problem that many CS majors face

[17:14]: Erika and Arnelle's opinion on the durability of American higher ed

[19:26]: Why diverse teams see problems that others can't

[24:48]: On who gets to start a startup

[27:28]: Favorite books and podcasts

Tim Harsch is the CEO and Co-Founder of Owler, a business insights company bringing transparency to private businesses around the world.

After joining the company as an Associate Product Manager out of college, Tim's relentless work ethic and technical expertise lead him to become the CEO of the company all before the age of 30.

We discuss the many use cases of Owler, why Tim never pictured himself leading a company, and keeping perspective on the different tiers of challenges in life.

[1:04]: The first company Tim ever started (Hint: it is not Owler)

[2:02]: A minimum wage job and Tim's first taste of Silicon Valley

[3:47]: How Owler is working to bring transparency to private businesses around the world

[5:50]: The challenges of running a distributed team with 70+ Owler team members based in India

[7:15]: Tim's path from Associate Product Manager to CEO of Owler

[8:58]: Reflecting on 8+ years at Owler, and what's next for the company

[11:12]: Why Tim never imagined in a million years he'd be doing what he does now

[12:59]: Unexpected use cases for Owler (Forestry and PE/VC)

[16:14]: Tim's favorite books and a shout-out to Eric Jorgenson

Allison Barr Allen is the Co-Founder and COO of Fast, a startup working to bring 1-click, passwordless checkout services to the five billion users of the Internet.

Previously, she served as the Head of Global Product Operations at Uber as the company scaled from 2,000 employees to more than 26,000 worldwide. She's also deeply committed to supporting entrepreneurs through Trail Run Capital, her Angel investment fund.

In this episode, we discuss Fast's recent $20M round lead by Stripe, Allison's love for marathon running, and what she look for in a startup when making an Angel investment.

[1:08]: Allison's initial interest in medicine leads her to PwC

[2:41]: Leaving PwC in 2014 to join Uber and advice for those looking to join a startup

[4:07]: Launching Uber's Driver Instant Pay feature and biggest learnings from scaling the company

[9:10]: How Allison got started with Angel investing and the birth of her Frictionless Finance thesis

[12:22]: The 3 things Allison looks for when investing in a startup

[14:35]: How a simple breakfast meeting to discuss an Angel investment turned into Allison becoming the COO and Co-Founder of Fast

[16:22]: How Fast is building a 1-click checkout for the entire Internet and their GTM strategy

[20:31]: Fast's recent $20M round lead by Stripe and how they plan to use the money

[23:12]: Allison's love for marathon running

[25:52]: Favorite books and podcasts, and a shout-out to Harry Stebbings

Blake Robbins is a partner at Ludlow Ventures. His unique combination of sincerity and grit is embodied by the early-stage firm itself.

We did an entire episode based off Blake's old Tweets. On influencers, creators, building a career with cold outreach, and writing checks from the heart of Detroit.

[0:57]: Why the new dream job is becoming a YouTuber

[4:30]: The 'Adpocalypse' and more creator-friendly platforms

[9:40]: Blake on hustling, Imposter Syndrome, and shamelessly Tweeting people

[15:29]: Ludlow's secret sauce

[19:57]: Professional athletes, gamers, VCs, and celebrities crossing over into different worlds

[24:06]: Favorite podcasts

[25:06]: Trying to value Blake's Twitter account

Alberto Arenaza is the co-founder of Transcend Network, a global fellowship for entrepreneurs focused on the future of learning and work.

He was also a member of the Minerva Schools' first graduating class — a journey which took him from Buenos Aires to Berlin, and now back to San Francisco. Hear why Alberto thinks this experience is an unfair advantage in supporting ambitious founders around the world.

[4:12]: Seeing 7 cities through Minerva's innovative model

[6:02]: The unique perspective and unfair advantage that world travel provides

[11:05]: Transcend's open theses

[16:44]: Alberto's take on the future of US higher ed

[19:35]: Why employers will shoulder the burden of upskilling and job retraining

[23:50]: On being frequently mistaken for Adam Neumann

[24:46]: Venture Stories, Origins and other recommendations

Mike Raab is the Director of "The Garage" in San Francisco, a coworking space that provides community and resources for Northwestern alumni, operators, and investors.

Previously, Mike was an investor at Sinai Ventures where he invested in early-stage consumer tech companies, and has a wealth of experience as a freelance writer with articles commissioned for Business Insider, OneZero, and HackerNoon.

In this conversation, he and Asher discuss similarities between the entertainment industry and venture capital, the importance of authenticity as a leader, and what makes for a fulfilling career.

[0:59]: Starting his career in the entertainment space with Fox after graduating from Northwestern

[2:08]: Why after 4 years at Fox, Mike quit his job to spend 3 months backpacking through Europe

[5:45]: Returning to Fox in a new role with a greater appreciation for having a daily routine

[7:21]: Joining Sinai Ventures in 2018 and similarities between entertainment and venture capital

[10:23]: Frustrations with VC, and moving into a new job at The Garage

[12:11]: The single strongest predictor of whether or not someone will be a good manager

[15:05]: Mike's thoughts on what makes for a fulfilling career

[17:21]: Why volume and quantity of the content we put into the world improves quality over time

DeWayne Johnson explains streetwear, overlap between the worlds of art and venture capital, cold outreach and his newsletter on marketplaces — Double Sided.

His job at Lambda School is to help other people get jobs. Hear DeWayne's uniquely inspiring story to understand why that work matters to him.

[0:55]: Similarities between the worlds of art and venture capital

[3:04]: What people don't understand about streetwear

[5:46]: Calling on Jeff Bezos' wisdom in deciding whether to drop out

[10:09]: Booking a one-way ticket for a coffee meeting with Ryan Delk

[13:24]: Finally getting a foothold in tech with a gig at TrueBill (YC W16)

[15:48]: Interning at Earnest Capital

[19:21]: DeWayne's job at Lambda School getting other people jobs

[27:06]: Favorite books and podcasts

Helena Merk and Brian Li started Glimpse (YC W20) with an ambitious goal: to combat loneliness and create the rare social product which actually makes us happier.

Its arrival couldn't be more timely. Hear their story and why early users are addicted to these 2 minute, one-on-one video chats.

[0:33]: Taking on loneliness and an early pivot

[5:55]: Lessons learned from past social products

[8:22]: The shift from content consumption to creation

[13:18]: Dropping out for YC W20

[20:17]: Why Glimpse is the perfect product for right now

[22:48]: Favorite books and podcasts

Varadh Jain is an angel investor and digital nomad currently doing one-off projects in different parts of the world.

Most recently, he spent three years as an early employee at Opendoor, helping to scale the company from 200 employees to nearly 1,500. Before that, he was on the founding team of Polymail (YC S16) and spent time at a seed fund in Los Angeles.

In this conversation, he and Asher discuss thinking about careers in seven year intervals, how Varadh got started with Angel investing, and being helpful to founders without necessarily providing advice.

[1:05]: Joining Polymail as Employee #1

[2:27]: Realizing his Visa was going to expire in 2016 and starting with the OpenDoor team

[3:31]: How Varadh's role at OpenDoor evolved over time

[5:10]: Biggest learnings from three years at a high growth tech company

[6:26]: Thinking about life in seven year chunks, traveling, and self-directed learning

[8:03]: Angel investing, being helpful to early-stage companies, and avoiding advice

[12:42]: What we can learn from drug cartels about how to run a successful business

Wes Wagner is a remote worker and former Head of Growth at Microverse (YC S19), a coding bootcamp with a unique model.

On this episode, he shares with Ethan what it's like to split time between Medellin and Indianapolis, why we should optimize for quality over quantity in our relationships and how he thinks about the future of education.

[1:21]: Wes' path to digital nomad life

[5:35]: Optimizing for quality over quantity of relationships

[6:56] Microverse's unique business model

[12:35]: Creating incentives to unearth talent in overlooked areas

[15:21]: Re-thinking YC in a modern context

[23:46]: Technology that can help us to be more intentional in our relationships

[30:06]: Trusting the process of learning in public

[33:11]: Zero to One, Homo Deus and other favorite books

Eric Jorgenson is a product strategist, writer and (rarely) an Angel investor. He is on the founding team of Zaarly, and has been publishing online since 2014. His business blog, Evergreen, has educated and entertained over a million readers.

He's also the author of the soon-to-be-released "Almanack of Naval Ravikant", a book of Naval's most valuable thoughts, tweets, and pieces of wisdom from the past decade.

He and Asher discuss how he came up with the idea of writing the Navalmanack, his first experience writing online with Evergreen, and reflecting on lessons learned after nine years with Zaarly.

[1:01]: Dropping out of school to join Zaarly in 2011

[2:34]: Why Eric would work for Bo Fishback—the founder of Zaarly—in a McDonald's

[4:02]: Narrowing Zaarly's focus to home service providers

[5:44]: How Eric's role within the company has evolved over time

[6:42]: Reflecting on 9+ years at Zaarly

[10:40]: How the idea for the "Almanack of Naval Ravikant" was born

[13:47]: Eric's favorite pieces of advice from Naval

[16:25]: Curating timeless business advice at Evergreen Library

[21:06]: Course Correctly and Eric's next project after he finishes the Navalmanack

[24:45]: Eric's love for "Poor Charlie's Almanack" and "The Systems Bible"

Justin Potts, co-founder and CEO of Avenify, joins Ethan to discuss their innovative lending platform for income share agreements. The marketplace allows top college students to finance their education debt-free, backed by investors who earn a return when they succeed.

Before launching, he and his co-founder Timo spent 3 months RVing to different colleges across the country. Hear how that's impacted the product, why they've largely eschewed the venture route and where they see tremendous opportunities to grow.

[3:31]: How Justin and Timo have leaned on angels, savings and crowdsourced funding for Avenify

[9:22]: Growing up in Texas, building apps and meeting his co-founder in college

[16:36]: Why they think nursing students are a perfect fit for their product

[19:58]: Joining the Product Hunt mafia

[22:54]: RVing across the country to hear students' stories and understand the market

[25:21]: Transparency, adverse selection and other common ISA concerns

[32:21]: Justin's affinity for a good startup story

Cameron Porter is an investor at AlleyCorp, a New York City based venture studio that's incubated the likes of Business Insider, Mongo DB, and more.

After leading all of college soccer in scoring his senior year at Princeton, Cam dropped out to play professional soccer in the MLS, while simultaneously working for the league as a software engineer.

He and Asher talk startup ideation, contextualizing his unconventional path into venture, and above all, why greatness can't be planned.

[1:08]: How AlleyCorp systematizes the process of startup ideation

[5:03]: From high school graduating class of 45 to the NCAA's leading goal scorer

[8:36]: Playing in the MLS while simultaneously working for the league as a software engineer

[12:07]: Optimizing for the average Wednesday

[13:56]: Where AlleyCorp differs from a typical VC firm

[17:10]: The mechanics of an ideation session and the process of talking to users

[23:57]: The story of how AlleyCorp was started

[29:30]: Optimizing for performance at work, content consumption, and what is worth Cam's time

[33:49]: Cam's favorite books and how they've changed the way he sees the world

In the latest episode of Worth, Asher sits down with Vedika Jain, ex-Stripe and True Layer, and currently the Chief of Staff at Weekend Fund.

Among other things, we discuss advice she received from Harry Stebbings on breaking into venture, ways in which Weekend Fund is looking to help founders from underserved markets, and what she believes makes a problem worth solving.

[1:05]: Rethinking a traditional childhood education

[4:18]: The story of how Vedika ended up at UC Berkeley and what makes a problem worth solving

[6:56]: Landing at Stripe and what made their culture so strong

[12:22]: Learning how to code and getting into flow at Le Wagon

[15:37]: Scaling True Layer from 7 employees to 70

[19:12] Advice from Harry Stebbings and joining forces with Ryan Hoover at Weekend Fund

[23:29]: Experimentation on the Weekend Fund model and lessons learned from Weekend Build

[34:06]: Roam Research and some trends Vedika feels strongly about

[37:07]: Vedika's favorite books and our mutual appreciation of Morgan Housel's writing

Among other topics, in the second part of this conversation we touch on mentors, college entrepreneurship and getting a foothold in venture.

Ethan sits down with Shawn Xu of Floodgate, recently named to Forbes 30 Under 30 in venture.

Shawn shares how his passion for different cultures has guided him from launching international markets at Square, to investing in brilliant student founders at Dorm Room Fund and now to learning under the legendary Ann Miura-Ko and Mike Maples Jr. at Floodgate.

Before all this, he was just a kid hustling for restaurant tips. Listen to his exceptional story and much more, here.

[1:33]: Growing up an immigrant in SF's backyard

[11:58]: How Shawn evaluates opportunities in international markets

[16:59]: Why business school is worth it sometimes

[19:45]: The exceptional Dorm Room Fund family

[22:26]: On being non-consensus and right

Mehak Vohra knew that dropping out at 19 was a huge risk. Since taking the leap in 2016, she's been featured by Forbes, ABC, Adweek, Huffington Post and a slew of other publications while growing her agency, Jamocha Media, into a six-figure business.

In this conversation with Ethan, she pulls back the curtain on her childhood, transitioning from college student to freelancer and scaling her newest project, OnDelta, a growth marketing bootcamp that's free until you get a job.

[1:25]: Running for Mayor of San Francisco

[5:33]: All things OnDelta

[11:15]: Growing up in West Virginia and Oakridge, Tennessee: birthplace of The Manhattan Project

[16:43]: How a single weekend changed the trajectory of Mehak's life

[21:02]: Jamocha Media as a vehicle for learning

[22:15]: The struggles of freelancing

[25:09]: Doubling down on LinkedIn

[27:41]: OnDelta as a "scaleable marketing agency"

[30:40]: Mehak's favorite book

In this episode, Asher speaks with Prateek Swain: recent Princeton graduate, and the 23 year old co-founder of GreenTiger, an app that allows people in India to trade U.S. stocks commission free.

After being accepted into Y Combinator's Summer 2019 batch, and being dubbed "Robinhood for India", we caught up with Prateek and talked about some of the best advice he got during his time at YC, and the challenges of starting a fintech company.

[1:55]: Prateek's experience building his first business, "Shuffl", in high school

[6:54]: Launching India's largest hackathon and Princeton's first startup incubator

[12:41]: Why Princeton lags behind Harvard/Stanford when it comes to entrepreneurship

[16:05]: Working for Microsoft and discontentment with corporate life

[18:06]: How the idea for GreenTiger was born

[23:15]: Applying to Y Combinator early-decision

[26:04]: The best advice that Prateek received during his time at YC

[29:41]: How Prateek and Tyler divide responsibilities and prioritize tasks at GreenTiger

[33:06]: The "Series A Challenge" and where GreenTiger's focus currently lies

[37:09]: Prateek's favorite books and his love for Paul Graham's essays

In this episode, Asher is joined by Jess Li, 23 year old VC at Soma Capital and former Partner at Rough Draft Ventures.

We talk through Jess' decision to not return to Morgan Stanley after her junior summer, her experience working for multiple Y Combinator backed startups, and how she thinks about career development.

[1:45]: Jess' background and childhood

[4:42]: Advice from her father and diving into the world of startups

[7:58]: Jess' ongoing work with Elpha (YC S19) - a Reddit type community for women in tech

[16:07]: Investing in student-led businesses at Rough Draft Ventures

[21:25]: Helping founders to see their blind spots and how VCs can add value

[24:43]: Joining Soma Capital and staying on top of 200+ portfolio companies

[30:52]: What Jess looks for when evaluating founding teams at the seed stage

[36:19]: Closing the door on an investment banking job at Morgan Stanley

[41:20]: Jess' favorite podcast and advice for her pre-college self