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The Bridge
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The Bridge

Author: 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.

91 Episodes
Mike Weiland, Co founder and CEO of Govly, joins the show to talk aboutWhy selling to the government is really hard and how Govly makes that easier for businesses contracting with the government.Raising $9.5M Series A from Insight, fundraising for a government tech startup, and the advantages of picking a more unique venture vertical that is recession proof.Raising the bar and challenging employees to achieve more, and how Govly did that to hit their revenue milestones ahead of raising their Series A.Founder/VC fit, and some of the proof points that validated that Insight was the right partner to help Govly scale its company.
Navneet Dalal, CEO and Co founder of Matic joins the show to talk aboutBeing 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".
Sam Chaudhary, Co founder and CEO of ClassDojo, joins the show to talk aboutWhere 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).
Siva Namasivayam, Co founder and CEO of Cohere Health, joins the show to talk aboutStarting 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.
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 spaceBuilding an "honor based" mindset to servicing the families who have lost loved ones.
Tony Jamous, Co founder and CEO of Oyster, joins the show to talk aboutGlobe 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 cultureA 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.
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?
Daniel Yanisse, Co founder and CEO of Checkr, joins the show to talk aboutThe 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 productFlying high and flying low. When and how a founder should get "in the weeds" when running their company.
Sukhinder Singh Cassidy, CEO of Xero, joins the show to talk aboutHer first exposure to entrepreneurship running the books for her father's businessHow 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.
Arjun Sethi, Founder of Tribe Capital, joins the show to talk aboutThe founding story and investment thesis behind Tribe CapitalFrom 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.
Job van der Voort, Founder and CEO of Remote, joins the show to talk aboutThe pain of hiring and onboarding remote employees, and the insight from GitLab that led to founding "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
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.
Josh Reeves, Co founder and CEO of Gusto, joins the show to talk aboutUsing 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 competitorsHow 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.
Christina Cacioppo, Co founder and CEO of Vanta, joins the show to talk aboutHow 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.
Joe Thomas, CEO and Co founder of Loom, joins the show to talk aboutHow Joe and team have scaled Loom to +21M active usersThe 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 applicationHow Loom is planning to use Generative AI to improve collaboration and leapfrog its competitors.
Bill Smith, Founder and CEO of Landing and Shipt (acquired by Target), joins the show to talk aboutMoving 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.
Rahul Vohra, Co founder and CEO of Superhuman, joins the show to talk aboutFounding 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.
Max Lytvyn, Co founder of Grammarly, joins the show to talk aboutPivoting from plagiarism detection to building Grammarly, one of the 20 most valuable startups in the USA 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.
NBA Champion, investor, and hoops analytics guru, Shane Battier joins the pod to talk aboutThe 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 basketballPlayer ownership and the evolution of player empowerment in professional sports.
Kaveh Khorram,  CEO of, 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's experience taking Usage from 0 to 1 and learnings from the scale and growth phase of his companyDiversifying and de-risking partner and platform risk, and predictions on where the future of the cloud is headed.
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