Insights from two years of “Driven” founders

Learnings from best-in-class founders, hackers & designers

One of the many benefits of my role at FirstMark is that I get to co-organize and attend 4 monthly events (FirstMark’s Driven Series: Data Driven, Design Driven, Code Driven, Hardwired). With 40 Driven events per year and roughly 150 speakers participating on an annual basis, I am fortunate to have met and heard from executive-level people — Founders, CEOs, CTOs, Creative Directors, Chief Data Scientists, Heads of Product & Design, etc.— from close to 300 of the top startups and technology companies around the world! The past two years at FirstMark have been an amazing real-world education, to say the least.

I recently reviewed my notes from each event and have catalogued some of my lessons learned below. A few important things to note up front:

(1) These aren’t the high-level lessons you hear all too often like “surround yourself with people smarter than you” or “culture is important”; rather, they are tactical, digestible insights that are partially actionable at the very least.

(2) These aren’t lessons I learned through personal experiences at FirstMark (that topic is more than enough for a separate post)— rather, they are some of the insights shared by our phenomenal group of speakers, who learned these lessons through their own personal and professional experiences.

(3) I’ve tried to categorize the insights below into themes and sub-themes, yet they may still seem fairly random or scattered. The lessons range from suggested design tactics (“Fitt’s Law”), to shipping methodology cost comparisons (air vs. ocean freight?), to migrating away from monolithic code bases (“BoundedContext”).

(4) Lastly, for those who are interested in general tech & market trends, I’ve also included some of the data-porn shared over the years toward the bottom of this post. This section quantifies trends (steam-of-consciousness style) ranging from the size of the overall pet market, to the pace of virtual reality consumer adoption, to the financial impact of Shark Tank on a given business.

My hope is that if you’re working in one, or across several, of these areas, you’ll be able to take away some key learnings that may benefit you, your team, and your business.

On Design and Product:

Internal Processes

  • Develop a naming convention for your design team and document everything. [Kim Bost, Dropbox]
  • There is a benefit to sharing incomplete work — it creates trust among coworkers and increases team motivation, so don’t hesitate to share unfinished designs. [Kim Bost, Dropbox]
  • Think about how to create an inclusive design process where BD, sales, and product teams drive the discovery, definition, and design of the product, and Engineering drives the rest until the release. [Will Martin, Floored]
  • Never direct your designers on what to do. Instead share your emotional feedback about their designs and allow them to come up with their new solutions. [Sara Chipps, Jewelbots]
  • Try to rid of internal emails completely because they get in the way of productivity. Instead, all members of the product and design teams should use Slack + GitHub + Sunrise + any other tools to keep your team out of their inbox. [Jeremy Le Van, Sunrise]

Product Design

  • Don’t forget about Fitt’s Law: the smaller the target, the longer it takes for the user to go to. Build large form fields and even larger CTAs. [Manuel Lima, Codecademy]
  • Don’t push feature updates live unless they are perfect. Users can perceive things that are off even if they can’t articulate them. [Rich Arnold, Vine]
  • Don’t use modals to request user reviews. Instead, put the request in the “What’s New” section in the App Store. This drives your best users to write good reviews for your product. [Michael Mignano, Anchor]
  • Design trends to think about when designing for millenials: large headlines, image-based articles, infinite scroll, and nav sidebars. [Liran Okanon, Mic]
  • In eCommerce, photos with no faces and tighter crops on the product perform greater (i.e. yield higher conversions) than full-body photos. [Talia Fisher and Ben Gelinas, JackThreads]
  • Moving the close modal button to the top left of the signup modal from top right resulted in 123% signup conversion and 68% less close modal rates on desktop. [Talia Fisher and Ben Gelinas, JackThreads]
  • With the emergence of mobile commerce, a mobile checkout redesign can lead to a drastic impact on the business (40% increase in conversions for Warby Parker). [Tim Riley, Warby Parker]
  • The Minimum Viable Product should not just be your first release — it should be every release. [Rohun Gholkar, NewsCred]
  • Design for kids and grandparents; UI and UX should be dead-simple. [Michael Mignano, Anchor]
  • You can balance playful graphics with serif typefaces to emphasize the seriousness of your product (e.g. for subway advertising). [Josh Long, Oscar]
  • Designing for Virtual Reality is difficult since there is no standardized controller across platforms (e.g. physical touchpad vs.virtual touchpad vs. eye gaze, etc.). [Andre Lorenceau, LiveLike]
  • Product & Design Tools / Stacks: For analytics, consider using Optimizely,, and Mixpanel; for prototyping, consider using InVision (disclosure: FirstMark company) and Sketch.
  • Over time, a strong brand can emerge as a result of prioritizing a great product. [Anna Bakst, Michael Kors]

Hiring, Team Building, and Team Structuring

  • 13 key characteristics to look for when hiring a designer: (1)Optimism; (2)Collaboration; (3)Embracing ambiguity; (4)Learning from failure; (5)Taking Ownership; (6)Talking less, doing more; (7)Documenting processes; (8)Being intentional; (9)Trusting oneself; (10)Making others successful; (11)Designing for outcomes; (12)Taking chances; (13)Generosity [David Goligorsky, Yieldmo]
  • Blur the lines between Design, Engineering, and Product teams; have designers ship code to production. [Cap Watkins, BuzzFeed]
  • Talent is what annoys you. Ask potential hires what bothers them or makes them feel uncomfortable. Their answers will reveal a lot about them. [Paul Ford, Author of What is Code?]
  • Don’t fire fast. People have risked steady jobs to join your risky startup. You should therefore, as a founder, be patient and give poorly performing employees some time to develop and correct themselves. [Bradford Shelhammer, Bezar]
  • Consider your designer:developer(:product manager) ratio. For a new product called “Mix”, for instance, FiftyThree made sure to maintain a 1:1 designer:developer ratio. [Paula Guntaur, FiftyThree]

On Hardware and Manufacturing:


  • Design → Manufacture → Fulfillment takes 12–24 months, so whatever you’re building should anticipate what the market will look like then. [Piet Morgan, Hammerhead]
  • The way you manufacture mostly depends on your production needs in year 3. [Danielle Applestone, Other Machine Co.]
  • It’s critical to get production samples in addition to prototype runs; your product may look and feel very different in real life than you had thought. [Adam Kalamchi and Kane Hsieh, Brilliant Bicycles]
  • Manufacturing an iPhone case in the US would raise the retail cost 2.5x; the packaging alone would cost more than the product itself. [Nora Levinson, Caeden]
  • China isn’t always the answer for manufacturing. Look to other areas like Mexico and the Philippines where costs may be higher but the corresponding quality and ease of communication are also higher. [Daniela Perdomo, goTenna]


  • Air freight is roughly 5x the cost of ocean freight, but can be even higher (7–10x) if it’s a peak time of year. Make sure to plan around busy “seasons”, including obvious ones (Christmas time) and non-obvious ones (when Apple plans to ship a new version of the iPhone). [Renee DiResta, Haven]
  • Be aware of the typical time it takes for a Hong Kong → LA shipment: Air = 13hrs , Ocean = 4 weeks. [Renee DiResta, Haven]


  • Rule of thumb for selling physical products: wholesale prices should be at least 4x your COGS, ideally 6x if you have significant customer support costs. [Inder Singh, Kinsa]
  • One simple way of testing consumer reactions to multiple price points is to A/B test prices on a product promotion landing page and evaluate the conversion rate for each price variation. 6SensorLabs tested 25(!) different pricing variations before settling on a go-to-market price for its gluten sensor. [Shireen Yates, 6SensorLabs]
  • Leverage software to update your hardware. By introducing new features to a device via software updates, you can eliminate (or at least minimize) constant manufacturing updates. [Piet Morgan, Hammerhead]
  • Watch your inventory levels like a hawk. There’s a fine line between under-stocked and over-inventoried. [Nora Levinson, Caeden]
  • Hardware markets become very fragmented quickly due to the ability to commoditize physical products; therefore, you must protect yourself with science, software, or a community (network effects). [Cyril Ebersweiler, HAX]


  • 3D printing is effective for creating products that require: (1)Low volume production; (2) Customization; (3)Complex Geometry. [Kegan Schouwenberg, SOLS]
  • …Yet there are still inefficiencies in 3D printing, including: (1)Cost: expensive raw materials; (2)Machines being built in low volume; (3)No full color plastic; (4)Speed: printing is too slow; (5)CAD software is complex. [Peter Weijmarshausen, Shapeways]
  • High-end headsets like Oculus and GearVR are currently generating publicity and awareness for VR, but most VR consumption in the future will take place on smartphones. [Jens Christensen, Jaunt VR]
  • In the future, no product will exist in isolation; all products will become part of the web. [Niall Murphy, EVRYTHNG]

On Data, Infrastructure, and Enterprise Tech:


  • If you’re selling B2B, don’t be the low-cost provider. [Anand Sanwal, CB Insights]
  • Be wary of regression models — you can’t rely too much on a regression model because it’s just one of many representations of the underlying reality. [Jeremy Achin, DataRobot]
  • Don’t mistake correlation for causation when analyzing data. [Jeremy Achin, DataRobot]
  • Hire salespeople who have experience selling into a certain type of business/end-consumer (e.g. SMBs), even if they are not technical or don’t necessarily understand your product. [Dan Scholnick, Trinity Ventures]


  • Deep learning has recently gained traction due to: (1)Enough large data sets becoming available; (2)Faster machines have enabled larger models; and (3)Many small algorithmic advancements over time [Richard Socher, MetaMind]
  • ML and AI models are improving, but they’re still only ~80% accurate. [Dan Scholnick, Trinity Ventures]
  • Some of the advantages of Apache Spark include: (1) Faster: optimized in-memory processing; (2) Easy to use API: has 100 operators beyond map and reduce; (3) Unified platform: supports streaming, interactive, query processing, and graph-based computation [Ion Stoica, Databricks]
  • Data prep is still the primary time-suck for data science teams. [Amir Orad, Sisense]

The Future

  • The next wave of enterprise software is all about selling to every level of the organization, including entry- and mid-level employees. [Ryan Smith, Qualtrics]
  • The shortage of data scientists in the future will be solved by a combination of pragmatic education (programs and real-world experience) and levels of automation currently not thought possible. [Jeremy Achin, DataRobot]
  • Delivering the correct sequence of questions tailored to each individual at the correct time is the Holy Grail of online learning. [Aaron Skonnard, Pluralsight]
  • Current BI tools answer important questions about the past, but the successful next-gen analytics tools will help drive predictive decision-making. [Satya Ramachandran, Neustar]

On Engineering & Engineer Management:


  • Management is about efficient allocation of resources and skills development. [Seth Purcell, Signpost]
  • Common ways for an engineering manager to fail: (1)Doing your old job and staying in the code; (2)Being reluctant; (3)Not hiring the best people; (4)Being an extremely “flat organization” [Seth Purcell, Signpost]
  • The goals of engineers and managers should be aligned. Everyone’s goals should be measured using a specific metric of success. All goals should be visible to everyone in the company. [Duncan Grazier, ShopKeep]
  • Formalizing an engineering culture is important beyond the value it provides to the engineering team. It helps engineers explain how they are going to help the company win. [Gil Shklarski, Flatiron Health]
  • It is extremely important to clearly articulate career paths. [Gil Shklarski, Flatiron Health]


  • It’s impossible for a distributed system to simultaneously deliver all 3 of the following: Consistency, Availability, and Partition tolerance (otherwise known as the CAP Theorem) [David Dawson & Alexandre Berke, Mast Mobile]
  • If you’re transitioning away from a monolithic code base, consider migrating toward BoundedContext: dividing code into models with explicit interrelationships. Team sizes for each model should fall between 4–6 engineers. [Kenny Chen, DigitalOcean]

On Markets and Trends:

  • The Shark Tank Effect: value of a 12-min primetime spot is $4M; 10M live viewers; 5X increase in sustained web traffic
  • 60% of luxury goods are purchased overseas (non-U.S.)
  • Time it took to reach 50M people: Radio = 38 years; Internet = 4 years; VR = 1 year
  • 60% of US households have a dog or cat; 90% of those owners view their pets as family
  • The pet market is 4x the size of the baby market
  • $10B wedding registry market
  • 42B+ customer service interactions per year
  • 300+ hours of video content uploaded to YouTube every minute
  • When eBay was founded, only 8 million websites existed. Today over 1 billion websites and over 1.4M apps exist
  • 97% of all cyber attacks originate through phishing
  • 80% of data has a location component, but only 10% of organizations are making use of it
  • VC investment dollars breakdown for VR from 2010–2015: 53% in content creation, 45% in displays, 2% in content distribution
  • Graphs are eating the world”: graph databases are the fastest-growing segment of databases
  • Data Scientist = a PHD who writes production code
  • Six Pillars of Commerce: Site design, Sent mail, Social, Shipping, Services, and Speed

Driven Series, by the Numbers (past 2 years):

90 Data Driven speakers, including:

  • Peter Fenton, General Partner at Benchmark
  • Mike Abbott, former VP Engineering at Twitter and General Partner at Kleiner Perkins
  • Renaud Laplanche, CEO of LendingClub
  • Aaron Skonnard, CEO of Pluralsight
  • Kieran Snyder, CEO of Textio
  • Ryan Smith, CEO of Qualtrics
  • Mike Olson, Chairman of Cloudera
  • M.C. Srivas, CTO of MapR
  • Liz Crawford, CTO of Birchbox
  • Eliot Horowitz, CTO at MongoDB
  • Rachel Schutt, Chief Data Scientist at News Corp
  • Catherine Williams, Head of Data Science at AppNexus
  • Yann LeCun, Head of Artificial Intelligence at Facebook
  • Mahmoud El Assir, SVP and CIO of Global Technology Services at Verizon

(see full list here)

90 Hardwired speakers, including:

  • Kegan Schouwenberg, CEO of SOLS
  • Jens Christensen, CEO of Jaunt VR
  • Peter Weijmarshausen, CEO of Shapeways
  • Daniela Perdomo, CEO of goTenna
  • Bre Pettis, CEO of MakerBot
  • Nikki Kaufman, CEO of Normal
  • Christina Mercando, CEO of Ringly
  • Luke Iseman, Director of Hardware at Y Combinator
  • Lior Susan, Partner at Formation 8
  • Brady Forrest, Vice President at Highway1
  • Cyril Ebersweiler, Managing Director of HAX
  • Mark Yahiro, Managing Director of Perceptual Computing at Intel

(see full list here)

60 Design Driven speakers, including:

  • Scott Belsky, Founder of Behance and General Partner at Benchmark
  • Anna Bakst, President of Michael Kors
  • Mauro Porcini, Chief Design Officer at Pepsi
  • Jeremy Le Van, Co-Founder of Sunrise
  • Alex Blumberg, Founder of Gimlet Media
  • Jeff Chapin, Co-Founder and CPO of Casper
  • Julie Logan, Director of Brand Strategy at Giphy
  • David Lee, Chief Creative Officer at Squarespace
  • Khoi Vinh, Principal Designer at Adobe
  • Cap Watkins, VP of Design at BuzzFeed
  • Deepa Subramaniam, former Head of Product at charity:water and Head of Product at Hilary for America
  • Nir Eyal, Author of Hooked

(see full list here)

20 Code Driven speakers, including:

  • Gil Shklarski, VP of Technology at Flatiron Health
  • James Turnbull, VP Engineering at Kickstarter
  • Duncan Grazier, VP Engineering at ShopKeep
  • Mat Brown, Lead Engineer at Genius
  • Alexandre Berke, Senior Engineer at Mast Mobile
  • Mariko Kosaka, Engineer at Scripto and Organizer of BrooklynJS
  • Spencer Kimball, CEO of Cockroach Labs
  • Max Krohn, CEO of Keybase
  • Alex Poon, COO of

(see full list here)

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