20VC: Inside The Acquisition Decision-Making Process at Cisco, How To Measure True Success in M&A Evaluation & Why By Not Speaking To Corp Dev Teams You Are Closing The Door On The Biggest Potential Accelerator To Your Business with Rob Salvagno, VP of Corporate Development and Cisco Investments


Rob Salvagno is VP of Corporate Development and Cisco Investments at Cisco, where he is responsible for leading all M&A efforts as well as managing Cisco’s strategic venture capital which invests hundreds of millions of dollars annually. At Cisco, Rob led the $1.2 billion acquisition of Meraki, one of the most successful platform acquisitions in Cisco’s history, and the $3.7 billion acquisition of AppDynamics, cementing Cisco’s place in the business intelligence, analytics and IT operations market. Most recently, Rob engineered the $2.3 billion acquisition of Duo, the leading provider of unified access security and multi-factor authentication delivered through the cloud. Prior to the world of M&A, Rob was a technology investment banker at Donaldson, Lufkin & Jenrette.



In Today’s Episode You Will Learn:

1.) How Rob made his way from investment banking to leading the M&A and venture activity for one of the world’s largest tech players of the last decade?

2.) How do M&A teams like to get to know startups that they could invest in or acquire? How does Rob like to work with the venture ecosystem? How does Rob think on Paul Graham’s comment of “do not talk to corp dev”? What are the nuances here? How does it differ for consumer vs enterprise?

3.) How does Rob define true success when it comes to M&A evaluation? Should corp dev be strategy first or transaction first? What have been Rob’s biggest lessons on successful integration? Where do so many go wrong with integration post M&A? What questions can be asked ahead of time to know if integration and culture will be a fit?

4.) How does Rob reflect on his own price sensitivity today? How does Rob feel about the multiples enterprise companies are currently trading at? What have Rob’s most successful acquisitions taught him about price and price sensitivity? How does Rob deal with the inherent conflict of investing and also acquiring companies? How does he communicate that to the companies he invests in?

5.) What does the acquisition-decision making process look like at Cisco? How does it differ on a deal by deal basis? What do Cisco do to allow them to move so much faster than any other M&A teams? What have been Rob’s lessons on the importance of speed in winning the best transactions?

Items Mentioned In Today’s Show:

Rob’s Fave Book: The Poisonwood Bible

Rob’s Most Recent Acquisitions: CloudCherry, Voicea

As always you can follow HarryThe Twenty Minute VC and Rob on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Most Downloaded Episode of 2019 with Bill Gurley, General Partner @ Benchmark Capital

Gurley Headshot

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO.



In Today’s Episode You Will Learn:

1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world’s leading funds in the form of Benchmark? What were Bill’s biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill’s investment mentality today?

2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, “never turn down a deal based on the valuation it is a mental trap”? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google?

3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays?

4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio?

5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition?

Items Mentioned In Today’s Show:

Bill’s Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos

Bill’s Most Recent Investment: Good Eggs

As always you can follow HarryThe Twenty Minute VC and Bill on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Inside UiPath, The World’s Fastest Growing Startup, How The Best Leaders Approach Decision-Making & WhY Vulnerability Is Central To SuccessFul Leadership Today with Brandon Deer, VP of Operations & Strategy @ UiPath

Brandon Deer Headshot

Brandon Deer is VP of Operations & Strategy @ UiPath, one of the world’s fastest-growing companies providing a complete software platform to help organizations efficiently automate business processes through robotic process automation. To date, UiPath has raised over $977m in funding from some of the best in the world including Sequoia, Accel, Meritech, IVP, CapitalG, Kleiner Perkins, Coatue and more. As for Brandon, prior to UiPath he spent 4 years as Vice President @ OpenView Partners where he made investments in Expensify, Logz.io, VTS and Pipefy to name a couple. Before OpenView, Brandon spent close to 4 years at Intuit in Strategy and Business Development.



In Today’s Episode You Will Learn:

1.) How Brandon made his way from being a rising star in the world of venture with Openview to leading one of the fastest-growing companies in history in UiPath? What has been the most surprising element in making the transition from investor to operator?

2.) How does Brandon think about decision-making today? How does he determine what to spend time on vs what to delegate? What does he mean when he says, “you have to think whether it is rubber or crystal?” How does that ultimately guide decision-making?

3.) What does the UiPath software actually do? What is the relationship between RPA and AI? Where do they differ? Where do they intersect? Recently, RPA has seen a meteoric rise, is this sustainable over the long term? How does Brandon respond to the suggestion that RPA is replacing human jobs? What is the human and societal impact?

4.) How does Brandon think about vulnerability in leadership? Why does Daniel and Brandon’s relationship work so well today? What has Daniel (Founder) taught Brandon about communicating that vulnerability the right way and authentically? What does Brandon advise founders in terms of being open to their vulnerabilities?

5.) What are the biggest challenges in scaling an organisation to the 1,000+ person organisation that UiPath is today? What breaks When does it break? How does one maintain culture wit such scale? What have been the challenges of building a truly global business from Day 1? How do they look to mitigate them?

Items Mentioned In Today’s Show:

Brandon’s Fave Book: The Five Temptations of a CEO: A Leadership Fable

As always you can follow HarryThe Twenty Minute VC and Brandon on Twitter here!

20VC: How To Think Through Portfolio Construction and The Business Model of VC, Why You Cannot Grow Ownership In Your Best Companies Over Time & How To Make The Space for Serendipity To Strike in VC with Adam D’Augelli, Partner @ True Ventures

Adam D'Augelli Headshot

Adam D’Augelli is a Partner @ True Ventures, one of the West Coast’s leading early-stage funds with a portfolio including the likes of Fitbit, Peloton, Hashicorp, Tray.io, Ring, Automattic (makers of WordPress) and many more amazing companies. As for Adam, he has spent close to 10 years at True where he has led investments in Hashicorp, Ring, Splice and Namely, just to name a few. Prior to joining the world of venture with True, Adam was an instructor at The University of Florida in Business Finance. Before that Adam was the Founder of Perfect Wave Records, a donation-based record label – helping bands better monetize the relationships with their fans.



In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of venture with True and how that start came about?

2.) How does Adam think about portfolio construction today with True? Is it still possible to get 20% ownership on first check? Does Adam believe you can build ownership in subsequent rounds? Does this mean we are seeing the end to rounds being co-led? What does Adam make of pre-emptive rounds? How do True respond to them today?

3.) How does True think about initial vs re-investment decision-making? How do the decision processes differ? Does Adam believe it is possible to stack rank companies and allocate capital accordingly? What is the right way to tell a founder you will not be re-investing? How does Adam think about risk maximisation at a company level?

4.) As a partnership, how does True look to create an environment of safety where both conviction and concerns can be expressed? What should partnerships not do? Why is attribution so dangerous to this EQ of the partnership? How does the partnership work with the companies at a company level? How does True view board seats? How does True think about when is the right time to roll off boards?

5.) What were Adam’s biggest takeaways from leading Ring’s seed to their acquisition by Amazon? How does Adam think about the importance of market vs the importance of people when investing? How does Adam think about company failure, post-mortems and subsequent next steps?

Items Mentioned In Today’s Show:

Adam’s Fave Book: Doing Capitalism in the Innovation Economy: Markets, Speculation and the StateTechnological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages

Adam’s Recommended Whitepaper: Investing in the Unknown and Unknowable

Adam’s Most Recent Investment: Membio

As always you can follow HarryThe Twenty Minute VC and Adam on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Unusual Ventures’ John Vrionis on Why We Need To Raise The Bar In Venture, Why Taking Multi-Stage Money At Seed Is Not In The Best Interest of Founders & Why To Be The Best, You Have To Specialise To Be The Best

John Vrionis Headshot

John Vrionis is the Founder and Managing Partner @ Unusual Ventures, the firm that is redefining seed investing and raising the bar for what entrepreneurs should expect from a seed investment firm. Prior to founding Unusual, John spent 11 years as a Partner @ Lightspeed where his investments included Mulesoft, AppDynamics, Nimble Storage and Heptio to name a few. Before Lightspeed John spent time in product management and sales @ Determina and Freedom Financial Network.



In Today’s Episode You Will Learn:

1.) How did John make his way into the world of venture and come to be a Partner @ Lightspeed? How did that lead to his founding Unusual? How did his father’s MS diagnosis change his mentality towards both investing and how he views the world? What were John’s biggest takeaways from his 12 years with the Lightspeed partnership?

2.) Where does John feel the bar needs to be raised in venture? What does the current product not offer? What do seed-stage founders fundamentally need? How have Unusual structured the firm to provide this? How was the fundraise for John? What does John know post-closing that he wishes he had known at the beginning? What advice would John give to aspiring emerging managers? Why is LP diversity so important to John?

3.) Why does John believe taking multi-stage money at seed is not in the best interests of the founder? How does John explain this logically to founders? Does John agree with Semil Shah, “founders are voting with their feet and choosing multi-stage funds”? Why does John believe to be truly best in class, you have to specialise? Does this not go against the data of Benchmark, Sequoia, Founders Fund, all generalist funds, having the best returns?

4.) How does John think about being company vs being founder first? What does one do when alignment erodes between the interest of the firm and the interest of the founder? How does John look to build a relationship of trust and honesty with his founders? What works? What does not work? How does John feel about VCs being friends with their founders?

5.) What is the most challenging element of John’s role today with Unusual? Who is the best board member John has ever sat on a board with? Why and what did he learn? What would John most like to change about the world of venture today? What would he like to remain the same?

Items Mentioned In Today’s Show:

John’s Fave Book: Shoe Dog: A Memoir by the Creator of NIKEGive and Take: Why Helping Others Drives Our Success

John’s Most Recent Investment: Shujinko

As always you can follow HarryThe Twenty Minute VC and John on Twitter here!

20VC: Why Raising A Mega-Round Makes Your Life Harder Not Easier, Why Your Board Is Not Your Boss and Lessons on Successful Board Management & The Biggest Breakpoints in Company Scaling with Emmanuel Schalit, Founder & CEO @ Dashlane


Emmanuel Schalit is the Founder & CEO @ Dashlane, the company that provides your all-in-one internet shortcut for passwords, payments and personal info. To date, Emmanuel has raised over $192m in funding for Dashlane from some of the best in the business including Jim Goetz @ Sequoia Capital, Rick @ Firstmark, Alex @ Bessemer and Habib @ Rho, just to name a few. As for Emmanuel, prior to founding Dashlane, he was the CEO @ CBS Outdoor in France and before that COO @ La Martiniere Group.



In Today’s Episode You Will Learn:

1.) How Emmanuel made his way from CEO of 5,000+ people companies to founding Dashlane and changing the world of passwords and identification? How does Emmanuel asses his own risk profile moving from CEO of a large company to starting Dashlane?

2.) Is Emmanuel concerned by the excess capital available today? Why does Emmanuel believe that raising a mega-round makes your life as a founder harder, not easier? What specifically becomes harder? How does Emmanuel advise founders when it comes to burn and capital efficiency? How does Emmanuel think about when is the right time to pour fuel on the fire?

3.) Where does Emmanuel think that VCs do tangibly add real value? Where does Emmanuel believe that despite what some think, VCs do not add value in certain areas? What have been Emmanuel’s biggest lessons of operating and managing a VC board? What does he advise founders starting out on this learning curve?

4.) What does Emmanuel believe are the core challenges of scale? What breaks at what specific points? How has Emmanuel seen himself scale in his role as CEO? What have been the most challenging element to scale into? How did Emmanuel get through them and what does he do to mitigate them now?

Items Mentioned In Today’s Show:

Emmanuel’s Fave Book: Sapiens: A Brief History of Humankind

As always you can follow HarryThe Twenty Minute VC and Emmanuel on Twitter here!

20VC: BoxGroup’s David Tisch on Whether Concentrated Investing At Seed Works, Do Founders Really Want Direct Feedback and Is It Good For Them & Why Consumer Social Is Interesting Again

David Tisch Headshot

David Tisch is the Founder & Managing Partner @ BoxGroup, one of the leading early-stage firms in NYC with a portfolio that includes the likes of Flexport, RigUp, Ro, Glossier, Clearbit, PillPack and Plaid, to name a few. Recently they raised their first external capital with 2 separate vehicles totalling over $160m. David is also Professor and Head of Startup Studio @ Cornell Tech. Prior to Box Group, he was Managing Director of Techstars NYC and before that was an Executive Vice President @ KGB.



In Today’s Episode You Will Learn:

1.) How David made his way into the world of early-stage investing? How he made the transition from prolific angel investor to raising $160m+ in external capital? Why did David feel now was the right time to raise external funding after 10 years of self-funding? How has taking on external capital changed his investing mindset?

2.) Many suggest that “concentrated seed investing does not work”, how does David think about and assess portfolio construction? May others also suggest that, “seed investors are not company builders”, does David agree with that? Does David believe investors can change the trajectory of a company? Where can they help the most? Where do many think they help but they actually do not?

3.) Why does David believe that founders do not speak openly about bad experiences with VCs? What have been David’s biggest lessons on the right way to turn down an opportunity? Do founders really want direct and honest feedback? Is it actually damaging to give it to them? Why? How does David approach this?

4.) Why does David believe “consumer social is interesting again”? Why was it not interesting for a while? How does that mean David is approaching the category? What does David mean when he says, “for the first time ever there is no channel to arbitrage on the internet”? Is David concerned by the state of CACs today? How much attention does David pay to CAC/LTV in the early days? What are the key signals?

Items Mentioned In Today’s Show:

David’s Fave TV Show: Survivor

As always you can follow HarryThe Twenty Minute VC and David on Twitter here!