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

Natasha's Twitter - https://twitter.com/nmasc_

Natasha's Substack - https://natasha.substack.com/

TechCrunch's Equity podcast - https://twitter.com/equitypod

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

Charlie's Twitter - https://twitter.com/charliecfeng

Clearbanc Website - https://clearbanc.com/

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

Stephanie's LinkedIn: https://www.linkedin.com/in/stephanie-bowker-b8172717/

Spendesk's Website: https://www.spendesk.com/

"How to Scale Product Marketing": https://www.youtube.com/watch?v=wcV5oJCSvQU&t=2300s

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

Edlyft's website - https://edlyft.com/

Edlyft's Twitter - https://twitter.com/TheEdlyft

Arnelle's Twitter - https://twitter.com/nelly_ans

Erika's Twitter - https://twitter.com/bballerika

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

Tim's Linkedin: https://www.linkedin.com/in/tharsch/

Owler Website: https://corp.owler.com/

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

Allison's Twitter: https://twitter.com/abarrallen

Fast Website: https://www.fast.co/

Fast Swag Store: https://swag.fast.co/

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

Tweet #1 → https://twitter.com/blakeir/status/1151885162726268928?s=20

Tweet #2 → https://twitter.com/blakeir/status/1238226009398312961?s=20

Tweet #3 → https://twitter.com/blakeir/status/1219786744796676096?s=20

Tweet #4 → https://twitter.com/blakeir/status/1227691448491008004?s=20

Tweet #5 → https://twitter.com/blakeir/status/1221259142553358336?s=20

Blake's Twitter - https://twitter.com/blakeir

Blake's writing - https://medium.com/@blakeir

Worth website - worth.carrd.co

Recommendations - https://www.notion.so/book-podcast-recommendations-59abba1db1db4fc2b9b9a4e08edb0b24

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

Alberto's Twitter - https://twitter.com/albertoarenaza?lang=en

Transcend Network website - https://transcend-network.com/

Transcend newsletter - https://transcend.substack.com/

Worth website - worth.carrd.co

Recommendations - https://www.notion.so/book-podcast-recommendations-59abba1db1db4fc2b9b9a4e08edb0b24

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

Mike's Twitter - https://twitter.com/hithereimmike

Mike's Blog - https://www.theraabithole.com/

The Garage Website - https://thegarage.northwestern.edu/

David Foster Wallace's "This is Water" Speech - https://fs.blog/2012/04/david-foster-wallace-this-is-water/

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

DeWayne's Twitter - https://twitter.com/dewayneroyj

DeWayne's website - https://dewayneroy.com/

Worth website - worth.carrd.co

Recommendations - https://www.notion.so/book-podcast-recommendations-59abba1db1db4fc2b9b9a4e08edb0b24