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cover art for The Impossible Hack, with Jasper Malcolmson CEO of Skylight Tools

The Medium Rules: Long-Term Trends in Media and Technology

The Impossible Hack, with Jasper Malcolmson CEO of Skylight Tools

If there was one area of the consumer economy that you may have thought might be impervious to the “direct-to-consumer” disruption of the past several years, good chance it would have been the home renovation market. Yet this high degree of difficulty also creates opportunity. On this episode of The Medium Rules, I sit down with JasperMalcolmson, co-founder and CEO of the digitally-native home renovation platform Skylight. By working with Skylight, homeowners can design, bid, project manage and pay for home renovations all through Skylight’s online toolset. Most notably, once a homeowner’s construction budget is locked, homeowners are protected from cost overruns through Skylight’s innovative “fully fixed pricing” guarantee. 

 

Prior to Skylight, Jasper founded the beloved local offers business Bloomspot, sold to Chase in 2012, and then Jasper stayed with Chase for 3 years as head of product at ChaseNet, Chase’s payments platform.  Previously, Jasper ran several business units at Yahoo!, principally under the leadership of Terry Semel. We talk to Jasper about working for Yahoo! in the early 2000’s, competing in the local offers space, his experience selling to Chase, and about the ambitions and challenges of Skylight amid the current startup climate in Silicon Valley. 

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  • 21. Aggregating and Innovating in Publishing with James Heckman, CEO of Maven.

    01:01:28||Ep. 21
    On this episode of The Medium Rules, I sit down with James Heckman to discuss his business philosophy animating Maven, as well as a look back at James’ career to date. Maven styles itself as a technology solution for publishers, centralizing and optimizing virtually all functions of a publishing business, from sales and marketing all the way through to legal and finance. And Maven is roughly modeled on two prior ventures founded by James, Rivals and Scouts, both sports-based publishing properties based on a similar “hub-and-spoke” approach to the publishing business in a digitally-native world. In this wide-ranging, informative and engaging conversation, James and I cover prior successes and failures, James' keys to success (net: strong team, reliable investors and high-quality partners), and what the future holds for Maven and the various brands it now owns and/or controls.  
  • 20. The Impeachment Trial with Adam Michaels & Mike Norton of HBA

    01:02:38||Ep. 20
    For this episode of The Medium Rules, the first of 2020, we decided to delve into the headlines and take an in-depth look at the impeachment trial of President Trump in the US Senate from a trial lawyer’s perspective. For this discussion I’m joined by two of my HBA colleagues: our head of litigation, Adam Michaels, and Partner Mike Norton, a former Assistant US Attorney for the Southern District who worked under Rudy Giuliani. We examine, among other topics, the concept of the Senate functioning as both judge and jury, the role and function of the media, the rules of evidence, the “presiding” role and function of Chief Justice Roberts (and what we might expect from Roberts in the coming days and weeks), and how all of these variables influence how a trial lawyer might approach the impeachment trial both as prosecution and defense.   We hope you tune in, watch and listen to this important conversation.  
  • 19. Network Effects, with Tim Gunderson of Carta

    53:21||Ep. 19
    Sometimes the biggest startup ideas are sitting right under our noses until somebody decides to just pick up and build the company. This is the case with Carta, which took an obvious pain point, the management of private company capitalization tables, and built a unicorn business. On the final episode of The Medium Rules for 2019, I sat down with Tim Gunderson, VP Products at Carta, to discuss how Carta took what might have seemed like a straightforward problem, built a simple cloud-based solution, and grew a company to a valuation of $1.7 billion (and counting!). In addition to great tech, the ubiquity of the cloud, a great founder and a great team, the magic insight here lies to a great extent in network effects: startups (in many cases with a not-so-gentle nudge from startup counsel!) go on the platform to reduce friction associated with cap table management, fund investors start to see the benefit of a high-level view of all of their portfolio investments and also urge companies to be on Carta, and finally fund LP’s are also pulled into the network to be able to easily view fund performance from the bottom up. We hope you tune in, watch and listen to this very lively season-ending episode. 
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    56:32||Ep. 18
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  • 17. AppNexus, AT&T and the Future of Media, with Michael Rubenstein President of AppNexus

    50:50||Ep. 17
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    51:53||Ep. 16
    With the explosion of podcasts and podcasting in recent years (there are 700,000 podcasts and counting, according to The New York Times), podcasting has become big business. In addition, there has been a recent spate of headline-grabbing podcast M&A activity, signaling that this new, highly intimate form of media is still in its early stages. However, the industry is struggling to find an advertising model that matches the growth and popularity of this new medium. Listener data is both very difficult to obtain and fragmented among the various industry participants, as a result of which ad-targeting, and CPMs, remain low.  Enter Podsights, a podcast analytics and attribution company co-founded by industry veterans Sean Creeley and Andy Pellett, which seeks to work with both the supply and demand side of the podcasting advertising business (call it “podtech”) to optimize both yield, on the one hand, and conversions on the other. Prior to co-founding Podsights, Sean founded a web attribution and analytics company by the name of Embedly, with Andy as his chief engineer. Embedly was sold to Medium Corporation in 2016.On this episode of The Medium Rules, Sean and Andy walk us through the various players in the podcast ecosystem, from the players to the hosting companies to the producers/creators to the brands and to the analytics companies in between. We talk about some of the newer entrants, such as Luminary, and we also discuss the current M&A environment, what the future might bring, and who will be the winners and the losers going forward.We hope you tune in, listen and watch this chatty and informative episode with Sean & Andy.
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    01:01:41||Ep. 15
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    55:07|
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    52:16||Ep. 13
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