The Bridge
Justin Vandehey
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The Bridge inspires founders to overcome barriers, build more efficient paths, explore new ideas, and connect with other entrepreneurs on the journey of building a generational company.
The Entrepreneur's path can be a lonely one. It doesn't need to be. Take the Bridge.
Available episodes
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10 hours ago
The future of "home automation" with Navneet Dalal, CEO and Co-founder of Matic, bringing AI & cutting edge robotics into your homes starting with the world's most advanced floor cleaner
Navneet Dalal, CEO and Co founder of Matic joins the show to talk about
* Being an early mover and pioneer in computer vision and deep learning.
* Moving beyond an interface and a good product to build a lasting, sustainable business.
* Being acquired by Google, working for Tony Fadell and with the Nest team, and the insight that led to Matic.
* The "human sensor stack" and how it intersects with the "robot sensor stack", and why Matic started with cleaning the floors.
* Picking an existing market and the importance of building a "minimum loveable product".
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Nov 17, 2023
It's for the kids!! ClassDojo CEO and Co founder, Sam Chaudhary on the problems and potential in early stage education.
Sam Chaudhary, Co founder and CEO of ClassDojo, joins the show to talk about
* Where early stage education is falling short, and Sam's experience building the largest community for teachers, parents, and kids to thrive in the educational system.
* The process Sam and his co founder Liam went through to unlock PM fit for ClassDojo.
* The jobs left to be solved in education, reflecting on the COVID home school experience, and how ClassDojo is expanding into the Virtual Learning Experience to solve the jobs that the classroom won't (or can't do well).
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Nov 10, 2023
Going from 0 to 1 in Health Care with Siva Namasivayam, CEO of Cohere Health
Siva Namasivayam, Co founder and CEO of Cohere Health, joins the show to talk about
* Starting companies in chaos and a family full of MDs.
* The inefficiencies that exist in the operational side of Health Care.
* Identifying early adopters and the nuances of doing that in a more conservative market like Health Care.
* Raising capital in health care and the traction you need and expectations you need to set before going out to raise capital in Health Care.
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Nov 3, 2023
"Death tech", the business behind death, and building an "honor based" mindset with Mallory Greene, Co founder and CEO of Eirene Cremations
Mallory Greene, Co founder and CEO of Eirene Cremations, joins the show to talk about
* "Death tech" and growing up in a family business centered on death.
* Why death is a great business, and the metrics that matter when raising capital in the Death Tech space
* Building an "honor based" mindset to servicing the families who have lost loved ones.
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Oct 27, 2023
The assumptions and excuses founders make from in-office culture, hiring the right C-Suite, and building from Cyprus with Tony Jamous, CEO of Oyster
Tony Jamous, Co founder and CEO of Oyster, joins the show to talk about
* Globe trotting from Lebanon to France to Cyprus, and the pains of starting a globally distributed business and the founding story of Oyster.
* The assumptions and excuses of an in-person office culture
* A purpose driven approach to company building, and why Tony built Oyster as a B Corp.
* Hiring the right people for the C-suite, and how Tony has approached executive hiring at Oyster.
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Oct 13, 2023
When is "too early" to ship product, and game changing SEO tactics with Farzad Rashidi, Co founder of Respona
Farzad Rashidi, Co founder of Respona, joins the show to talk about:
* The process Farzad went through to calculate customer acquisition costs and find the channel that ultimately led to founding Respona.
* A brief history of SEO, and a few hacks that founders can apply to grow their business.
* Tactics for podcasters to grow their own listener base + how Farzad landed an interview on this show.
* Balancing speed with quality, and when is "too early" to ship your product?
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Oct 6, 2023
Flying high, flying low, and eliminating hiring bias with Daniel Yanisse, Co founder and CEO of Checkr
Daniel Yanisse, Co founder and CEO of Checkr, joins the show to talk about
* The insight from building a startup in the gig economy to founding Checkr.
* Eliminating bias in the hiring process to help prospective hires live the dream.
* How founders should evaluate M&A opportunities and when it makes sense to acquire another company.
* Going up market into selling to larger enterprise with your product
* Flying high and flying low. When and how a founder should get "in the weeds" when running their company.
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Sep 29, 2023
Sukhinder Singh Cassidy, CEO of Xero on the importance of tailwinds, and "macro" and "micro" startup environments
Sukhinder Singh Cassidy, CEO of Xero, joins the show to talk about
* Her first exposure to entrepreneurship running the books for her father's business
* How Sukhinder has thought about evaluating the entrepreneurial ventures she has taken on, and how she evaluates the importance of the market/opportunity, and team she's building.
* How Xero is using AI to help support small businesses, and opportunities that Sukhinder sees for small business to save time and money.
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Sep 22, 2023
Take your time. Take your control. And a "bottoms up" approach to investing with Arjun Sethi, Founder of Tribe Capital
Arjun Sethi, Founder of Tribe Capital, joins the show to talk about
* The founding story and investment thesis behind Tribe Capital
* From being kicked out of high school, to joining the army and founding startups.
* Transitioning from Social Capital to Tribe, and "bottoms up" approach to investing.
* Arjun's experience gaining leverage through bootstrapping, and differences between raising capital for your startup and raising for your investment fund.
* The humbling experience of raising capital for Tribe, building the firm from the ground up, and a quantitative approach to demonstrating firm performance.
* Arjun's perspective on the current state of crypto.
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Sep 15, 2023
The superpowers that AI will give employees with Job van der Voort, CEO of Remote
Job van der Voort, Founder and CEO of Remote, joins the show to talk about
* The pain of hiring and onboarding remote employees, and the insight from GitLab that led to founding Remote.com.
* The "superpowers" that AI is going to give employees in this new era of work.
* Whether or not remote employees are as productive as their in-person colleagues.
* Job's reflections on the company he started before Remote
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Sep 8, 2023
Super Bowl champ, JuJu Smith-Schuster and CEO of World Champion Fantasy, Mike Vela on future of eGaming and fantasy sports
Super Bowl champion and New England Patriot, JuJu Smith-Schuster and CEO of World Champion Fantasy, Mike Vela, join the show to talk about:
* JuJu and Mike's perspective on the future of eGaming and Fantasy Sports
* How JuJu, Mike and team at WCF are reimagining the Fantasy Sports experience with the PlayerX Portal.
* The evolution of player empowerment and player ownership in ventures on and off the field.
* JuJu's mentality around the business and game of football and player brand.
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Sep 1, 2023
How Gusto used "Word of Mouth" to grow to more than 300K customers with Josh Reeves, CEO and Co founder of Gusto
Josh Reeves, Co founder and CEO of Gusto, joins the show to talk about
* Using Word of Mouth growth to over 300,000 business customers
* Battling against payroll giants like Intuit and ADP to build a category leader, and how much attention Josh pays to competitors
* How payroll is evolving, and how Gusto is innovating to support small business on a global scale.
* The advice Josh gives founders building their first company from his first startup prior to Gusto.
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Aug 25, 2023
Building a Unicorn in security with Christina Cacioppo, CEO and Co Founder of Vanta
Christina Cacioppo, Co founder and CEO of Vanta, joins the show to talk about
* How Christina's experience as a PM at Dropbox gave her the insight to starting Vanta.
* Current state of the security and compliance industry and why it's primed to explode.
* The impact that AI will have on security.
* Should founders raise strategic capital? And at what stage does it make sense to do so?
* Your startup is special, but not THAT special, and the hiring plan to support it.
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Aug 18, 2023
"Earned insights" and scaling Loom to +21M users with Joe Thomas, CEO and Co founder of Loom
Joe Thomas, CEO and Co founder of Loom, joins the show to talk about
* How Joe and team have scaled Loom to +21M active users
* The decision to hold on monetizing Loom until Year 3 of the company, and why founders should use activation as a success metric.
* The "earned insight" that led the Loom team to build a horizontal application vs. vertical application
* How Loom is planning to use Generative AI to improve collaboration and leapfrog its competitors.
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Aug 11, 2023
Disco's first customer! Founding and selling Shipt to Target for $550M, re-imagining home rentals with Landing, and the future of real-estate with Bill Smith, Founder and CEO of Landing
Bill Smith, Founder and CEO of Landing and Shipt (acquired by Target), joins the show to talk about
* Moving from Birmingham to San Francisco, the insight that led to Landing, and re-imagining how we rent homes.
* The remote work debate. Which hires should be in person and which hires can thrive remotely.
* Founder insights from building and selling Shipt to Target for $550M, and the differences between founding Shipt and Landing.
* The future of home rentals and how AI will impact the real estate category.
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Aug 4, 2023
A Superhuman approach to PM fit, virality, and emails that don't suck with Rahul Vohra, Co founder and CEO of Superhuman
Rahul Vohra, Co founder and CEO of Superhuman, joins the show to talk about
* Founding Rapportive, selling to Linkedin, and the insight that came from filtering every idea through the lens of our most valuable asset. Our time.
* The Superhuman Product Market Fit Engine and Rahul's method of quantifying whether or not you've found PM fit.
* A vision driven approach vs. a metrics driven approach to building your company, and the importance of balancing the two.
* The lattice model of virality, the desire to be more like our bosses, targeting the leadership layer, and how to unlock vertical and horizontal virality.
* At what point can (and should) a startup afford to compromise on talent.
* Superhuman AI and rewriting the future of email.
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Jul 28, 2023
More than words! Max Lytvyn, Co founder of Grammarly on building one of the 20 most valuable startups in the US
Max Lytvyn, Co founder of Grammarly, joins the show to talk about
* Pivoting from plagiarism detection to building Grammarly, one of the 20 most valuable startups in the US
* A 16 year "overnight" success story. Building and innovating when your vision is ahead of what's technically possible.
* Direct to consumer or B2B? How founders should evaluate building a direct-to-consumer vs. B2B, and how Max and team did both successfully.
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Jul 21, 2023
NBA Champion Shane Battier on the pivot from the front court to the front office
NBA Champion, investor, and hoops analytics guru, Shane Battier joins the pod to talk about
* The transition from playing alongside Lebron, D Wade, and Chris Bosh to the front office leading analytics for the Miami Heat.
* "Burning the ships". Shane's decision to go "all-in" on basketball and the parallels to founding a company.
* The impact that generative AI will have on the business and game of basketball
* Player ownership and the evolution of player empowerment in professional sports.
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Jul 14, 2023
Cleaning up "cloud waste" in the midst of the cloud wars with Kaveh Khorram, CEO of Usage.ai
Kaveh Khorram, CEO of Usage.ai, joins the show to talk about:
* Eliminating "cloud waste", creating a new category in the midst of the cloud wars, and the importance of timing when creating Usage.ai.
* Kaveh's experience taking Usage from 0 to 1 and learnings from the scale and growth phase of his company
* Diversifying and de-risking partner and platform risk, and predictions on where the future of the cloud is headed.
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Jul 7, 2023
A safer way to release software and the 0 to 1 story behind LaunchDarkly with Edith Harbaugh, Co founder of LaunchDarkly
Edith Harbaugh, Co founder and Executive Chair at LaunchDarkly, joins the show to talk about
* The process LaunchDarkly went through to validate PM fit and create the category for feature management.
* LaunchDarkly's target customer profile when finding PM fit and how their target customer profile has evolved as their category and company has scaled.
* At what stage in a company's growth should a founder invest in Dev Ops.
* The evolution of DevOps landscape over the next 3-5 years.
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Jun 30, 2023
CEO Succession draft with my co founder and brother, Jeremy Vandehey
CEO Succession draft! My co founder and brother Jeremy joins the show to analyze the top 10 CEO successors of the past two decades
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Jun 23, 2023
Crossing the second chasm and doing big BD deals with Kurt Davis, author of "Navigate the Lighthouse"
Kurt Davis, Co founder/CEO of Biteline and author of "Navigate the Lighthouse" and the BD aSaaSin, joins the show to talk about:
* International deal making and how Kurt approached doing large carrier BD deals in the early days at Boku.
* The process of crossing the second "chasm". What is the second chasm and how founders should approach it.
* Navigating the lighthouse and when a company should make their first BD hire.
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Jun 16, 2023
Hiring and building with AI, life before and after raising $40M, and the startup scene in Chicago with Scott Kacyn, Co founder and CTO of Hunt Club
Scott Kacyn, Co founder and CTO of Hunt Club, joins the show to talk about:
* Hunt Club's process of finding PM fit, startup life before and after raising $40M, and creating the category of Network Relationship Management in the process.
* The impact that generative AI will have on the hiring space.
* How Scott is using Copilot to support his engineering team in building Hunt Club
* Creating a startup in Chicago, Jay Cutler love, and the outlook on the Chicago Bears in 2023.
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Jun 9, 2023
Launching Harry's and Hims brands, Direct WITH Consumers, and building an emotional connection with a spatula with Suze Dowling, Co founder of Pattern Brands
Suze Dowling, Co founder and Chief Business Officer of Pattern Brands, joins the show to talk about
* Unlocking direct to consumer businesses and creating a successful multi-brand model.
* The value in developing a brand that resonates with your personal stage of life, and how to define successful brand and buying personas.
* The differences between operating an agency and operating a startup.
* Direct WITH consumer vs. Direct TO Consumer and creating with your customer.
* Suze's evaluation framework for M&A and the brands that Pattern acquires.
* When it does and doesn't make sense for a brand to open up a brick and mortar location.
* The secret sauce to finding an underserved category for DTC disruption.
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Jun 2, 2023
Life of the Solopreneur with Terry Rice, host of "Launch Your Business" on Entrepreneur
Terry Rice, Host of Entrepreneur's "Launch Your Business" podcast and author for Entrepreneur Media joins the show to talk about:
* How Terry got on Jason Feifer's radar (Editor in Chief at Entrepreneur Media), and how he turned that interaction into his dream job.
* Terry's process for launching his own consulting practice, finding your zone of genius, and tactics to take your consulting practice from 0 to 1.
* Going solo and making it as a solopreneur, the "10 questions" framework, and where Terry gets the inspiration for the content he creates for Entrepreneur.
* An awkward afternoon with the Rapper TI.
* Launching the "Launch Your Business" podcast and landing the right guests for your show.
* The two biggest mistakes that Terry sees solopreneurs making and how to fix them.
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May 26, 2023
Founding WeWork, the WeWork Culture OS, and building a better community for our elders with Miguel McKelvey, Co founder of WeWork
Miguel McKelvey, Co founder of WeWork, Proto, and Nayah joins the show to talk about
* How Miguel got the inspiration for founding WeWork and how he and Adam approached finding PM fit.
* The cultural challenges WeWork faced in the early days as the company scaled, and creating WeWork's Culture OS (Operating System) to scale culture.
* Founding Proto and building a more inclusive brand of footwear.
* Supporting our elders and building a better community for our aging population with NAYAH.
* Pick up hoops and the venture that Miguel wishes someone would start!
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May 19, 2023
What VCs ACTUALLY mean with Ann Miura-Ko, Founding Partner at Floodgate
Ann Miura-Ko, Founding Partner at Floodgate joins the show to talk about
* Founding a Venture Capital firm in the midst of a financial crisis.
* How founders should be thinking about their business and communicating to VCs at the pre-seed, seed, and Series A stages of company building.
* Why VCs say no and why Floodgate said no to Disco.
* What VCs actually mean when they say they're "investing in the founder, not the idea".
* The company that Ann wishes someone would start.
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May 12, 2023
Founding NerdWallet, when to hire your replacement, and the future of FinTech with Jake Gibson, Co founder of NerdWallet and Founding Partner at Better Tomorrow Ventures
Jake Gibson, Co Founder of NerdWallet and Founding Partner at Better Tomorrow Ventures, joins the show to talk about
* Founding NerdWallet, building a public company, and pioneering in the early days of financial services on the internet.
* The right time to replace yourself in order to help your company scale.
* Investing in the future of FinTech, embedded FinTech and rethinking the interface of Financial Services.
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May 3, 2023
The "dos and don'ts" of selling your company with Chris Buttenham, CEO and Co founder of Obie (acquired by Seismic)
Chris Buttenham, CEO and Co Founder of Obie (acquired by Seismic), joins the show to talk about
* How Chris' experience installing security cameras that led to the customer insight behind founding Obie
* Creating and falling into startup categories
* The process Chris took to successfully sell Obie to Lessonly and Seismic.
* Suggestions on how to grow the aSaaSins podcast
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Apr 28, 2023
It takes a village!! Raising little humans and childcare in a global pandemic with Gretchen Salyer, CEO of June Care
Gretchen Salyer, CEO and Founder of June Care, joins the show to talk about
* The childcare crisis in the US, and parenting and homeschooling in a global pandemic.
* Building a MVP for a better way to child care through community.
* How June Care's service model and product has evolved as they've received customer feedback from Moms on the network.
* The time I almost had my wife accidentally arrested.
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Apr 21, 2023
How Generative AI will transform engineering and the ethics behind it with Lauren Peate, CEO and Founder of Multitudes
Lauren Peate, CEO and Founder of Multitudes, joins the show to talk about
* The future of engineering and how teams use DORA metrics to measure engineering effectiveness.
* The importance of focusing on team outcomes and goals as an engineering leadership team.
* The impact that Generative AI will have on engineering team performance and productivity
* Ethics in AI and how entrepreneurs should respond to build to a higher standard.
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Apr 14, 2023
Swimming with the Sharks, battling the sun, and fighting mosquitos with Nichole Powell, CEO and Founder of Kinfield
Nichole Powell, CEO and Founder of Kinfield, joins the show to talk about
* Nichole's decision to make a professional pivot out of big tech to building clean, sustainable,consumer products for the outdoors.
* Nichole's experience appearing on Shark Tank, swimming with the sharks and receiving four different offers from investors to build Kinfield.
* How Kinfield has approached building product in a way that aligns with its core values and commitment to consumer health and sustainability.
* How Nichole and team have approached product segmentation for their various product lines and Kinfield's positioning strategy in retail.
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Apr 7, 2023
The business of sports and building a content empire with Joe Pompliano, CEO and Co founder of Huddle Up
Joe Pompliano, Co founder and CEO of Huddle Up, joins the show to talk about
* Two Billion social impressions, 25M YouTube views, and the journey to building one of the most successful content platforms for the business of sports.
* How Joe landed podcast guests like Ice Cube, Troy Aikman, Lance Armstrong, and others.
* How Joe evaluates the companies he invests in, and his perspective on working with his brothers and winning as a family.
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Mar 31, 2023
Landing Steph Curry as an investor and disrupting the miles, points, and rewards space with Henry Shi, Co founder of Super.com
Henry Shi, Co founder of Super, joins the show to talk about
* Building a savings super app focussed on the everyday American, and Super's approach to customer segmentation.
* Henry and Hussein's approach to finding product market fit for their consumer focused startup, and Henry's thoughts on how this differs from finding PM fit in building a B2B company.
* Super's initial focus on the travel vertical, and what they learned in the process of shipping their first product that accelerated their business growth and expansion into other product verticals.
* How Super has secured $100M+ in financing and landed the real baby faced assassin Steph Curry, as an investor in the business.
* The product market model channel (PMMC) fit and getting all four right to build a hundred million dollar plus business.
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Mar 24, 2023
How communities build stronger companies with David Booth, CEO of On Deck
David Booth, CEO of On Deck, joins the show to talk about:
* How On Deck helps founders get leverage on their time and lean into community to build exceptional companies, as well as how On Deck differs from traditional accelerators like YC and 500 Startups.
* David's "three edges" framework to evaluate On Deck's founder candidates, and evaluating the mindset that many founders have before taking the leap to start their companies
* The importance of building founder relationships and communities in-person, and the evolution of the "Sand Hill Road" entrepreneur.
* David's advice to founders and companies operating in our current market conditions, and who has the better job, founders or investors?
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Mar 17, 2023
Philz Coffee founder, Jacob Jaber (aka the Caffeinated aSaaSin), on creating company culture one cup at a time
Jacob Jaber, Chairman and Co founder of Philz Coffee joins the show to talk about:
* The founder's story behind building one of the industry's most successful specialty coffee brands.
* Creating a culture of "Grandma's house hospitality" and a personalized approach to building product and delivering service to customers, one cup of coffee at a time.
* How Philz harnessed initial customer fandom and built the flywheel around the Phil's brand.
* The role of the Philz barista, finding and empowering great people to extend the culture you're creating.
* Competing against global coffee brands like Starbucks and Peets, disrupting the coffee space, and thinking big but acting small
* How a lost bag at an airport resulted in a game changing distribution deal with Virgin America.
* Jacob's focus as an investor and building companies and products that people have a personal relationship with.
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Mar 11, 2023
SVB fallout and recap from MIT Sloan Sports Analytics Conference
Justin rounds out the week with a quick recap from the MIT Sloan Sports Analytics Conference and talks about
* The future of fan engagement and personalization in sports.
* The evolution of the athlete, player empowerment, and the "look at me" generation
* Leadership lessons from WNBA legend, Sue Bird, Miami Heat VP of Analytics, Shane Battier, and Celtics GM Brad Stevens.
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Mar 3, 2023
Disrupting FedEx and UPS and the future of the shipping industry with Ben Emmrich, CEO and Co founder of Tusk
Ben Emmrich, CEO and Co founder of Tusk joins the show to talk about:
* Disrupting FedEx and UPS with a better way to ship.
* The process Ben went through to sell and establish Tusk's first network partners.
* Diagnosing customer pain by checking the labels on the purchases we make every day.
* Ben's hustle selling dry ice and his approach to constructing monopolies.
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Feb 24, 2023
Bootstrapping to a $93M exit with the diagonal aSaaSin, Jesse Lipson, CEO and Co founder of Levitate
Jesse Lipson, CEO and Co founder of Levitate and ShareFile, joins the show to talk about
* Bootstrapping his SaaS company, ShareFile, to a $93M acquisition by Citrix.
* What the acquisition process looked like during the sale of ShareFile to Citrix.
* The keys to building successful companies with and without venture capital.
* Becoming the diagonal aSaaSin and dominating in categories that cut across verticals.
* Building really big businesses in the Raleigh tech scene.
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Feb 17, 2023
Brand and positioning from 0 to 1 with the marketing aSaaSin, Stephanie Bowker, Co Founder of Ourspace
Stephanie Bowker, Co Founder and CMO of Ourspace, joins the show to talk about
* The "people puzzle problem", and the biggest challenge individual contributors face as they transition to managers of people.
* The rise of the marketing aSaaSin and why marketers make great founders.
* Brand building and positioning during the stage of going from 0 to 1.
* The growth of the international tech scene and founding a company from Paris.
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Feb 10, 2023
Building a unicorn and becoming a technical founder with Bryant Chou, Co founder and CTO of Webflow
Bryant Chou, Co founder and CTO of Webflow, joins the show to talk about
* Bryant, Sergie and Vlad's journey to building a unicorn, and the three signals that gave Bryant conviction they were on to something really big with Webflow
* Bryant's suggestions for entrepreneurs looking for a technical co founder and traits of what makes an exceptional founding CTO
* Webflow's origins as a self-service business and how the company has matured into an enterprise grade solution
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Feb 3, 2023
Leaving the tech industry to start a restaurant with Bryan Tublin, Owner and Co Founder of Kitava
Bryan Tublin, Owner and Co Founder of Kitava, joins the show to talk about
* Taking the leap to leave a stable tech job to start a restaurant.
* How Bryan validated the concept for his restaurant by bringing soup to house parties.
* His process for gathering customer and employee feedback to inform his menu and dining experience
* Bryan's decision to expand Kitava to multiple locations and how he used partnerships to test new markets before going all-in.
* Gourmet PB&Js and growth hacking through pop-up stands and food trucks.
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Jan 27, 2023
Founding a unicorn and the future of remote work with Howard Lerman, CEO and Co founder of Roam and Yext
Howard Lerman, CEO and Co founder of Roam and Yext joins the show to talk about
* Building Yext, pivoting after $20M in ARR, and replacing the Yellow Pages
* Whether or not remote work is here to stay, the impact of the Zoom meeting boom, and the death of the recurring meeting with Roam.
* The importance of founder stock and making employees founders.
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Jan 20, 2023
Founding Lyft, "fork in the road moments", and dropping out of MIT to build the dream with Raj Suri, CEO and Co founder of Presto
Rajat Suri, CEO and Co founder of Presto and previous Co founder of Lyft joins the show to talk about:
* The customer insight that led to starting Zimride (aka Lyft)
* "Fork in the road" moments that have defined Raj's career as an entrepreneur.
* The thought process that led Raj to drop out of MIT to wait tables in a restaurant, and ultimately found Presto.
* Raj's decision to take Presto public and what that process looked like.
* Presto's position as an anti-metaverse idea and opportunities for automation in the physical world.
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Jan 13, 2023
Building a big business in cannabis with Roger Obando, Co founder and CTO of Baker
Roger Obando, CTO at Loyalsnap and Co founder of Baker Technologies (acquired by TILT Holdings), joins the show to talk about
* The evolution of the cannabis space, customer segmentation in weed, and the customer profile of the Chardonnay mom!
* Roger and team's experience raising capital for Baker, and his experience authoring his book, "The Highest Common Denominator",
* The differences of being a CTO that takes a company from 0 to 1 and a CTO that takes a company from 1 to 100 (and beyond).
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Jan 6, 2023
The right time to pivot and putting out fires with Bill Clerico, Founder of Convective Capital and CEO and Co founder of WePay
Bill Clerico, Founder and Managing Partner at Convective Capital, and Co founder and CEO of WePay, joins the show to talk about
* Building companies in a recession and Bill's model for evaluating investment opportunities.
* How Bill and his team uncovered PM fit for WePay, and the signals that helped WePay make the transition from a consumer to B2B company.
* Current state of the payments industry and picking categories that are less evolved for disruption.
* Hiring the right profile of employee for the right stage of your venture.
* Bill's advice for navigating the fundraising market over the next 18 months as a startup founder, and why more founders should be building in climate, and more specifically, fire tech.
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Dec 30, 2022
From player to coach with Brian Wang, Founder of Dashing Leadership
Brian Wang, founder and executive coach at Dashing Leadership joins the show to talk about:
* The similarities and differences of starting a venture backed startup and a coaching and services business.
* How early stage startup founders and leaders can get the best out of their people, specifically creating an environment that encourages risk taking and setting a clear short term AND long term vision.
* How founders can build more successful relationships with their investors and the importance of pushing back and embracing difficult conversations with your investors.
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Dec 23, 2022
Cam Doody, Co founder and GP of the Brickyard and Bellhop, on "insulating" startups and a better approach to finding PM fit
Cam Doody, Co founder and GP of the Brickyard, joins the show to talk about:
* Cam's first successful venture, Bellhop, and how he scaled one of the fastest growing companies in the moving industry.
* Brickyard's approach to accelerating and "insulating" great companies
* The benefit of relocating your early team to an island and the importance of physically working together in the early stages of building your culture and company.
* The best advice I've heard someone offer a founder when going through the grind, courtesy of Mr. Doody Sr.
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Dec 16, 2022
Putting chickens on Mars, the future of AgTech, and building the world's largest decentralized food production network with AJ Forsythe and Jordan Barnes, Co founders of Coop
AJ Forsythe and Jordan Barnes, Co founders of Coop, join the show to talk about
* Building the world's largest decentralized food network.
* The future of AgTech and putting automated agriculture systems on the moon.
* Pros and Cons of raising (and then being asked to spend) Venture Capital.
* Most importantly, unpacking what a cheese factory is all about.
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Dec 9, 2022
Stefan Seltz-Axmacher, CEO and Cofounder of Polymath Robotics on the future of robotics, autonomous vehicles and "right place, right time".
Stefan Seltz-Axmacher, CEO and Co founder of Polymath Robotics, joins the show to talk about
* The importance of timing when tackling an emerging category.
* How Polymath thinks about customer segmentation and the customer profile(s) it's solving for.
* Finding the right technical co founder and building a strong engineering team.
* Opportunities for automation in specific verticals and the future and role of robots over the next 50 years.
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Dec 2, 2022
Beers, brats, and business with Troy Vosseller, co founder of the Gener8tor accelerator and Sconnie Nation (On Wisconsin!!)
Troy Vosseller, Co founder of the Gener8tor accelerator and Co founder of Sconnie Nation joins the show to talk about
* Troy's experience founding a startup accelerator, and the similarities and differences of being an entrepreneur and investor.
* The story behind Sconnie Nation and how Troy established a meaningful and lasting brand.
* How Troy got into the business of selling his own brand of beer, and how he thinks about category expansion.
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Nov 25, 2022
The future of the film and entertainment industry with Alan d'Escragnolle, CEO and Co Founder of Filmhub
Alan d'Escragnolle, CEO and Co Founder of Filmhub, joins the show to talk about
* How Filmhub approached the BD and enterprise sales process to secure distrubtion deals with incredible partners like Amazon Prime Video, Tubi, and The Roku Channel.
* The importance of focusing on partners that have high growth potential, versus only focusing on partners with the greatest market share.
* The future of the film and entertainment industry, democratizing film production, and spitballing ideas for TV series that could be huge (or fail miserably)
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Nov 18, 2022
The birth of the "portfolio aSaaSin" and the history and future of marketing automation with Anu Shukla, Co founder of Tapjoy and Botco.ai
Anu Shukla, Co founder and Executive Chairman of Botco.ai, joins the show to talk about:
- The keys to finding product market fit as an entrepreneur, and her experience finding product market fit, multiple times, in various market conditions.
- Anu's experiences as a pioneer in the marketing automation space, as well as the ups and downs of building on someone else's platform.
- Anu's evolution as an entrepreneur from a specialist to a portfolio aSaaSin.
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Nov 11, 2022
Building a vertical SaaS powerhouse in salons with Matt Danna, CEO and Co Founder of Boulevard
Matt Danna, CEO and Co Founder of Boulevard, joins the show to talk about:
- How Matt uncovered product-market fit in the salon category
- Boulevard's approach to customer segmentation and targeting, and the company's decision to build a vertical SaaS business versus horizontal SaaS business.
- Matt's approach to fundraising, and how he closed a 70M Series C during one of the most difficult times to fundraise.
- The best and the worst haircuts we've ever received.
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Nov 4, 2022
Automation and AI in the enterprise with Rob May, Cofounder and CTO of Dianthus
Rob May, Serial entrepreneur and CTO and Cofounder of Dianthus joins the aSaaSins Podcast to discuss:
- His decision to start a company that wasn't SaaS first, and how Rob and his team are disrupting eCommerce.
- The evolution of AI and automation in the workplace, and what's missing for the space to really take off.
- Industries that are ripe for disruption through practical applications of automation, and the three criteria that make them candidates to target.
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Oct 28, 2022
Acquiring your first 10 customers with Jen Abel, Co founder and Partner of JJELLYFISH
Jen Abel, Co founder and Partner of JJELLYFISH joins the show to talk about:
* The importance of having the founder involved in the sales process when going from 0 to 1.
* The point at which founders should hire their first full-time sales person.
* The signals that companies and founders should be looking for to know when they've hit Product-Market fit.
* Using customer feedback to inform how your customers want to buy from you and how much your customers want to pay you.
"There's nothing scaleable about uncovering an earned insight." - Jen Abel, Co founder and Partner of JJELLYFISH
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Oct 21, 2022
The sibling episode! Brothers Dave and Nate Evans, co founders of Fictiv, on building a company with your sibling
Nate and Dave Evans, brothers and co founders of Fictiv join Jeremy and me on the show to talk about
- How Nate and Dave combined their unique interests and strengths as kids to build Fictiv. Dave's ability to break things and Nate's ability to think strategically.
- The process that Nate and Dave work through to make critical business decisions, and avoiding the 'Mom and Dad Syndrome'.
- The importance of not having the 'sibling debates' in public or in front of other work colleagues, and advantages of having an established baseline of trust over other co founders.
- How Nate and Dave have prioritized building a diverse team as they've grown and scaled Fictiv.
- The most important founder sibling questions: Who has a better jump shot? Who would win in a head-to-head wrestling match? Who is smarter?
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Oct 17, 2022
Money Morning Quarterback: Puttshack takes a $150M swing at the mini golf experience
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Puttshack, an upscale, tech-infused, mini golf experience. He analyzes their $150M growth round from BlackRock to takeover the indoor entertainment market.
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Oct 14, 2022
The future of investment banking and financial services with Federico Baradello, CEO and Co founder of Finalis
Federico Baradello, CEO and Co founder of Finalis, joins the show to talk about
- The evolution of the investment banking space and the opportunities to innovate in the back office of the financial services space.
- Finalis' 'five year overnight success story' and finding product go-to-market fit through 200 failed sales calls.
- Key insights and recommendations for first time founders building products in FinTech.
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Oct 10, 2022
Money Morning Quarterback: Tumble's $7M Series A to take down coin operated laundry
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Tumble, a smart laundry technology platform for property managers and renters. He unfolds their $7M Series A and the opportunity that Tumble is going after in the laundry industry.
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Oct 7, 2022
Legendary educator Esther Wojcicki and CEO Ari Memar talk about disrupting early stage education
Legendary educator and the Godmother of Silicon Valley, Esther Wojcicki, and her co Founder and CEO of Tract, Ari Memar, join the show to talk about:
- Esther's approach to empowering kids to be successful and how to raise successful kids.
- How Ari and Esther are disrupting early stage education with collaborative, peer to peer learning.
- Esther's experience working with her daughters, Anne (CEO of 23andMe) and Susan (CEO of YouTube) as her investors, and the dynamic of mixing family and business.
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Oct 3, 2022
Money Morning Quarterback: Artly Coffee's $8M Series A to make the perfect cup of coffee
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Artly Coffee, an AI-powered machine that makes a perfect cup of coffee every time. He unpacks their $8M Series A and the opportunity that Artly has in the coffee industry.
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Sep 30, 2022
Applying behavioral science to your venture with Kristen Berman, CEO & Co founder of Irrational Labs
Kristen Berman, Co founder of Irrational Labs joins the show to talk about:
- When companies should look to behavioral science to help answer critical questions about their businesses.
- Practical examples and applications of behavioral science that founders can use to drive better outcomes for their startups.
- The three B model of behavioral change and the irony and importance of adding friction to drive better results around onboarding and sign-up flows.
- The importance of asking for help when making friends.
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Sep 26, 2022
Money Morning Quarterback: (Warning, HOT episode) Pano AI's $20M Series A to help fire professionals fight wildfires
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Pano AI, a hardware and software platform that helps fire professionals detect threats and respond to fire emergencies faster. He unpacks their $20M Series A and the opportunity that Pano has to help fight wildfires.
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Sep 23, 2022
Bootstrapping to profitability with Laura McGee, CEO and Co founder of Diversio
Laura McGee, CEO and Co founder of Diversio joins the show to talk about
- Laura's experience raising capital for Diversio.
- How she bootstrapped the company to profitability before raising capital.
- The current state of the technology industry as it pertains to diversity, equity, and inclusion.
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Sep 19, 2022
Money Morning Quarterback: Chris Yeh and Justin break down Verkada's $205M and Tract's $7M rounds
On the aSaaSins 'Money Morning Quarterback' segment, our hosts Justin Vandehey and Chris Yeh break down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin and Chris play 'Money Morning Quarterback' with Verkada, an enterprise building security company, and Tract, a community and content marketplace for student-directed learning. They unpack Verkada's $205M round and Tract's $7M round.
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Sep 16, 2022
Beyond the Series A and the future of leadership coaching with Christine Tao, CEO and Cofounder of SoundingBoard
Christine Tao, CEO and Cofounder of SoundingBoard joins the aSaaSins Podcast to discuss:
- The future of leadership coaching and disrupting a category that has traditionally been limited to the highest earners in society.
- The challenges she faced when raising her seed round and additional challenges that female founders face when raising venture capital.
- The differences between raising SoundingBoard's Series B vs. their Seed and Series A.
- How Christine built SoundingBoard's initial network of leadership coaches, and importance of experience quality when building out the hard side of their network.
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Sep 12, 2022
Money Morning Quarterback: Muck Rack's MASSIVE $180M Growth Round to build the system of record for Public Relations
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Muck Rack, a Public Relations Management platform. He unpacks their $180M growth equity round and analyzes the opportunity in the media intelligence and PR space.
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Sep 9, 2022
Selling Troops to Salesforce and the differences & similarities of building B2B and D2C companies with Dan Reich, CEO and Co founder of Troops
Dan Reich, Co founder and CEO of Troops.ai joins the show to talk about:
* The story behind founding Troops and the sale of Troops to Slack.
* The story behind founding TULA, an industry leader in the skincare business, and the sale of TULA to P&G.
* The biggest differences and surprising similarities of running an enterprise SaaS business and D2C skincare company (and how to apply best practices across both business types to one another)
* His perspective on managing stress and pressure as an entrepreneur, and the importance of "thinking bigger" when building your business.
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Sep 5, 2022
Money Morning Quarterback: (TIMBER!!) Yesler's $5M Round for it's Lumber and building materials marketplace
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Yesler, a lumber and building materials marketplace. He unpacks their $5M round and analyzes the opportunity in the lumber management space.
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Sep 2, 2022
Tech accelerators, Disco's first check, and the 500 Startups experience with Marvin Liao, Partner at Diaspora and former GP at 500 Startups
Marvin Liao, Founder and Partner of Diaspora Ventures and formerly a General Partner at 500 Startups joins the aSaaSins podcast to talk about.
- What are Marvin's assessment criteria for investing in pre-seed and seed stage companies.
- How long after a company joined 500 Startups did he know if a company was going to make it or not, and what differentiated those that made it from those that didn't.
- How the incubator model is changing and evolving, and what this means for the future of seed stage companies going through incubator programs.
- How to improve your odds at getting accepted into an early stage accelerator, and alternative approaches and options founders can take to get support to go from zero to one.
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Aug 29, 2022
Money Morning Quarterback: CurbWaste's $6M Seed Round
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with CurbWaste, a waste management and business operations platform for physical waste haulers. He unpacks their $6M seed round and analyzes the opportunity in the waste management space.
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Aug 26, 2022
The product framework that could save your startup with Jon Fasoli, Chief Product Officer of Mailchimp
Jon Fasoli, Chief Product Officer of Mailchimp, joins the aSaaSins podcast to talk about.
- How he assesses the professional opportunities and projects that he invests his time and energy into.
- His experience running the product strategy for Intuit's $12B acquisition of Mailchimp.
- Future growth drivers and industries of interest for Intuit.
- Intuit's framework of 'horizon planning' and how early stage founders can use this framework to evaluate the progress they're making with their venture.
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Aug 22, 2022
Money Morning Quarterback: Incredible Health's $80M Series B
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Incredible Health, a medical and health platform that connects health systems with nurses. He unpacks their $80M Series B round and analyzes the healthcare technology industry's first health talent unicorn.
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Aug 19, 2022
How Daniel James, CEO and co founder of Zen, is improving employees' physical posture with intelligent security posture
Daniel James, CEO of Zen, joins the aSaaSins podcast to discuss:
- How Daniel's experience transitioning from being a Division 1 collegiate athlete to a working professional led to the opportunity around improving posture at work.
- How Daniel and his team have navigated questions and concerns around privacy while building a solution that's providing real customer value.
- Daniel's focus around building an experience that meets employees where they work.
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Aug 15, 2022
Money Morning Quarterback: Boulevard's $70M Series C and Ben's $16M Series A
On the aSaaSins 'Money Morning Quarterback' segment, our hosts Justin Vandehey and special guest host Chris Yeh break down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin and Chris play 'Money Morning Quarterback' with Boulevard, a platform that helps appointment based businesses (like Spas and Salons) streamline their operations, and Ben, an employee benefits and rewards platform. They unpack Boulevard's $70M Series C and Ben's $16M Series A.
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Aug 12, 2022
The manager that saved my career, BJ Schaknowski, CEO of symplr
BJ Schaknowski, CEO of symplr joins the aSaaSins pod to talk about:
- How BJ helped me "flip the switch" from being a disengaged poor performer to becoming a top performer at Intuit.
- BJ's guidance on effective leadership and the importance of balancing the "what" (work output) with the "how" (how we accomplish those objectives).
- The importance of being direct and helping your teammates understand the "why" behind your actions.
- The value and importance of bringing your authentic self to work, maintaining a learning mindset, and building a diverse and balanced team.
- BJ's decision to join and lead symplr, his noble purpose, and the opportunity to achieve better health outcomes through the business he's building.
- What should first time founders be thinking about if they want to start a venture in healthcare.
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Aug 8, 2022
Money Morning Quarterback: Arena's $32M Series A
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Arena, a platform that helps large enterprises make high frequency decisions (like pricing and inventory) fully autonomously. He unpacks their $32M Series A round and analyzes the market opportunity in the Big Data and Business Analytics space..
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Aug 5, 2022
Raising strategic capital and M&A with Ram Jambunathan, GM and SVP of SAP.io (SAPs strategic investment and incubation arm)
Ram Jambunathan, SVP and GM of SAP.io (SAP's strategic investment and incubation arm) joins the aSaaSins Podcast to discuss:
- Ram's experience as a founder, advisor and investor, and how those experiences have shaped his approach to supporting early stage founders.
- What founders should think about when raising capital from strategic or corporate investors.
- The real incentives behind corporate strategic investment.
- How corporate development and M&A really work inside of a large enterprise software company.
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Aug 1, 2022
Money Morning Quarterback: Sage's $9M Seed Round
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Sage, a platform that helps improve care with better caregiver tools that ensures older adults receive individual care. He unpacks their $9M Seed round and analyzes the market opportunity to improve the caregiver and resident experience inside assisted living facilities.
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Jul 29, 2022
Going after huge markets and large incumbents with Jay Srinivasan, CEO Spoke
Jay Srinivasan, CEO of Spoke, joins the aSaaSins podcast to talk about.
- Going after large incumbents like ServiceNow, SAP, and Salesforce, and how he landed on the problem space for Spoke.
- The differences between being a second time aSaaSin vs. a first time aSaaSin, and what has been easier and harder about each venture.
- Advice he WOULDN'T offer to first time founders and when is the right time to sell your startup.
- The importance of product, go-to-market fit when scaling, and why this is more important than product-market fit.
- Walking through the acquisition process for Jay's two startups, Appurify (Google) and Spoke (Okta).
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Jul 27, 2022
Getting above the noise and captivating audiences with Ben Parr, President of Octane AI
Summary:
- Ben shares how Octane thought about early traction channels and platform partners when launching their business. Specifically their partnership with Shopify.
- He discusses the process he went through in writing and authoring his book, "Captivology".
- Ben provides suggestions on how entrepreneurs can tap into 7 different triggers to get above the noise and captivate audiences to grow their startups.
- How Ben got Rick Ross and DJ Khaled's attention.
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Jul 25, 2022
Money Morning Quarterback: FairPlay's $10M Series A
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with FairPlay, the world's first Fairness-as-a-Service company, to unpack their $10M Series A round and analyzes the market opportunity to make applying for a mortgage a more fair and transparent process.
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Jul 22, 2022
Building network effects and growing a business in travel during a global lockdown with Cody Candee, CEO of Bounce
Cody Candee, CEO of Bounce joins us to talk about:
- How global travel unlocked his insight to found Bounce, and how he convinced total strangers to hand over and store their things with him for cash.
- Cody's experience building a company that was dependent on travel in the midst of global travel lockdowns, and how his team persevered through that.
- The signals that gave Cody and his team conviction to keep going, and how taking a 'helpful' approach to building solutions for their SMB customers unlocked new opportunities.
- Tactics on establishing and maintaining network effects at the earliest stages of founding your company.
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Jul 20, 2022
Early days at Slack and building a company on someone else's platform with Jassim Latif
Jassim Latif, Cofounder of Zipper and formerly Slack's first Platform and BD hire, joins the pod to talk about.
- Reflecting on the early days at Slack.
- Building an early ecosystem and raising capital on someone else's platform.
- Gathering insights to build Zipper and unlock cross functional teams.
- The boldest things founders have done to get on Jassim's radar and hacks to get on larger platforms' radars.
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Jul 18, 2022
Money Morning Quarterback: Aquabyte
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Aquabyte, an AI Aquaculture company, to unpack their $25M Series B round and analyzes the market opportunity that technology has in the commercial fishing industry.
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Jul 15, 2022
Veronica Belmont on becoming a startup's first hire and building communities from day one.
Veronica Belmont, Product & Evangelism leader at Adobe (and Disco's first hire!) joins the show to share some insight into:
* How we convinced her to join as our first product hire.
* How values, culture, and company mission played into her selection criteria when joining our startup.
* The value of onboarding employees through the lens of customer support to gain empathy
* Recommendations on how to build and foster community at the earliest stages.
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Jul 11, 2022
Money Morning Quarterback: StyleScan's $1M seed round
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with StyleScan, a virtual dressing room, to unpack their $1M seed round and analyzes the market opportunity in fashion tech to decide whether or not he'd invest.
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Jul 8, 2022
Closing your first investor check, Schuyler Brown, Cofounder of strongDM
This episode features cofounder of strongDM, Schuyler Brown as he shares his story on how strongDM raised its first round of financing BEFORE building their product. He also talks about turning down his offer to join YC, the time they almost gave away a car to build hype, and how to run a fundraising process that maximizes your startup value.
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Jul 1, 2022
The best sales and founders pitches with former 500 Startups pitch coach, Andrea Barrica
This episode features legendary 500 Startups pitch coach and founder of sexual wellness company, O.school, Andrea Barrica where we talk about
- The psychology behind the founder's pitch
- How timing and hype cycles influence pitch strategy.
- The similarities behind selling money and sex
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