Founder Real Talk

Anne Raimondi is an industry veteran with over 20 years of experience driving growth for B2B and B2C companies - taking them from startups to nationally recognized brands. Currently, she is the Chief Customer Officer for Guru, a leading AI knowledge management platform. Prior to Guru, Raimondi served as the SVP of Operations for Zendesk. Prior to Zendesk, Raimondi served as a product leader and executive for technology innovators - including Survey Monkey, TaskRabbit, Blue Nile and eBay. Anne holds an M.B.A. from Stanford University and currently lives in the Bay Area. In this episode, we learn from Anne why face-to-face engagement with customers and prospects is critical and why we should stay in cross-functional pods for as long as possible. Anne encourages founders to hire inherently curious “evangelists” who are already passionate about your product. Pro tip from Anne: The quickest way to end internal debates about what should or shouldn’t be built is to listen to customers talk about their pain points. Listen to the full episode for more pro tips. This episode was recorded live at the first annual SMB Tech Summit, co-hosted by GGV Capital, NFX and Fenwick & West. Episode Highlights: 01:41 If you’re building a company that’s going after the SMB, your functions need to be tightly aligned within the organization. What are tricks of the trade to make sure that happens? 03:41 So how do you build a management team that can manage cross-functionally, particularly with sales? 05:14 What can go wrong and what can go right when hiring more traditional enterprise folks into a company focused on the SMB space? 07:33 As a Chief Customer Officer now and you’ve seen a lot of great companies this world, what are the hacks to make sure your customers are happy, but that you’re not spending a lot of time and resource making that so? 10:39 What have you seen work well related to renewal rates? 13:25 What have you seen work well is you’re attempting to grow accounts? 15:45 For renewal and for expansion who should own those within a company that’s going after SMB? 17:12 What benefits do you get from segmenting your customers? 19:55 What about Net Promoter Score NPS. Is it a useful tool, how is it used well, and when it goes awry, what problems do you need to avoid? 20:47 Is the move up market deliberate and when do you know you’re ready? If it’s not deliberate, how do you make sure you don’t mess it up? 22:27 [question from the audience] How do you maintain connection and understanding of customers as humans as the companies you’ve been with have grown?

Max Levchin is the Founder & CEO of Affirm a financial services technology company that offers microloans to consumers at the point of sale. Affirm allows shoppers to pay for purchases across multiple months with transparent, fairly priced fees built into every payment. Max is also the Co-Founder and Chairman of Glow, a data-driven fertility company, and was one of the original co-founders of PayPal where he served as CTO until its acquisition by Ebay in 2002. He has served on several boards such as Yahoo!, Yelp, and Evernote. Max is an engineer by training, serial entrepreneur, computer scientist, investor and philanthropist. In this Founder Real Talk / 996 crossover episode, we learn how Max used the guiding principle of HVF (Hard, Valuable, Fun) to found Affirm. Max talks about writing a pivotal note to self to crystalize what he wanted to accomplish and how the financial industry is ripe for disruption. This episode is co-hosted by Glenn Solomon and Hans Tung. [03:14] Why is and how is affirm hard, valuable and fun? [09:06] There's obviously a very well established banking industry that you're kind of going up against in some ways. What about that industry makes it ripe for disruption? [15:08] Can you talk about how do you manage to figure out who to underwrite and avoid fraud. [16:29] So given the business you guys are in, are there any new wrinkles that you've had to deal with? [21:13] How have you been able continue to create a differentiated product and what does it take for you to stay ahead of your competitors? [26:27] Some of the merchants that you work with have told us a sales conversion with you has increased by as high as 30%. How are you able to do that? [28:02] What techniques have you used to maintain such a high NPS score? [29:41] How do you use data as an advantage in your company and when you advise startups, what do you tell them about use of data? [32:42] When you look back in your career, how have you seen yourself grown as a leader? [36:33] Did you come up with the core values before founding the company on your own or was it a team effort? [38:53] How have you approached diversity and inclusion and what have the benefits been for you? [42:33] What made you decide on Pittsburgh and how did you come to the decision to have a second office? [43:54] How do you solve for engineers and product people in different offices? [46:29] What's your schedule like? How do you feel about working smart vs. working hard? [52:42] Lightning round

Rich Waldron is the Co-Founder and CEO of Tray.io, a next gen workflow and integration technology company that allows automation of business processes without IT. Tray puts the power in the hands of non-technical users or “citizen automators” to quickly integrate the myriad cloud solutions that every company runs today to easily build and streamline bespoke workflows. In this episode, we learn how Rich and his two co-founders and lifelong friends, Ali and Dom, built a competitive product and high growth company with customers the likes of Lyft Forbes and New Relic. Rich explains how Tray has leveraged London and SF offices to define and maintain a strong company culture and shares tips for founders who are fundraising. Episode Highlights: 01:43 How did you decide to come together with your co-founders and what problem were you guys trying to solve initially? 03:43 How and why did the vision for the company expand beyond just email? 07:01 In the beginning, did you raise very little capital by design or was a result of a difficult situation? 15:24 How does the team stay in sync across offices in two continents? 18:15 What problems are your customers are having and why do they use Tray? 20:06 Do you feel Tray is part of the “low code, no code” movement”? 22:06 How do you rise above the noise in the market and handle your competition? 24:03 Why do you think Tray has hit on such a tremendous growth curve in the market? 25:24 How has word of mouth enabled Tray to grow rapidly? 26:16 What are you noticing to date as the difference between serving mid-market type customers and larger enterprise? 29:22 As your team grows, how are you trying to maintain the team spirit that you built with your co-founders? 30:56 How did you make the decision to raise early when the market gave you the signal that it was ready to invest? Any tips for others who are working with VCs? 35:40 How do you think about the future and what are you trying to accomplish? 39:33 What’s your recommended reading for other founders? 43:22 What’s your top piece of advice that you've gotten as a startup founder that you you would like to give to others?

Dave McJannet joined HashiCorp as CEO about three years ago when the company was approximately 30 people. Today the company employs more than 400 people, the company’s value has grown more than 20x and customer adoption for both the company’s open source platform and enterprise products have exploded. Prior to joining HashiCorp, Dave ran marketing at GitHub and HortonWorks, and earlier in his career spent time at VMware, Microsoft and webMethods. In this episode, we dig into HashiCorp’s growth and how it balances open source communities and enterprise revenue models, Dave’s journey to becoming the CEO and his relationship with HashiCorp co-founders Mitchell Hashimoto and Armon Dadgar, and the secret to selling software to large enterprises. Episode Highlights: 02:36: What’s it like to join a startup as a CEO when you’re not the founder? What are some of the challenges? 05:23: What made you think you were the right CEO for the CEO role at Hashicorp? 06:40: How to do split things up – between yourself and the two co-founders? 08:05: How do you manage disagreements? 08:54: How does your open source business model work? 10:40: Are there key indicators or metrics that you use to monitor the health of the business? 12:05: How do you think about time and resource allocation between the open source and commercial sides of the business? 13:11: How much time are the founders spending with open source communities vs. commercial customers? 14:15: How do you prioritize what's going to be part of the open source roadmap and what you're going to keep for commercial? 15:50: What do you need to do to be successful in selling to the enterprise as a young company? 17:39: In selling to the enterprise, it is just fake it till you make it? 19:21: How big a deal is support when working with enterprise customers? 20:05: What value do you get from your user conference? Do you recommend annual events for users? 22:08: As you scale from different revenue phases, what have you had to re-tool? What’s on your mind next? 25:07: What's your favorite book that you recommend for founders? 25:33: If you were a investor or board member in a Series A or B company what's the one piece of advice you'd give to the founder? 26:12 What's a company that you admire and why?

Kevin Hartz is one of the few leaders in Silicon Valley who has had an incredible career as a repeat founder, business builder and investor. He co-founded Eventbrite, the born digital ticketing leader, in October 2005 with his wife Julia Hartz and Renaud Visage. Kevin served as Chairman and CEO through late 2016 before turning the CEO reins over to Julia while remaining Chairman. Eventbrite had a very successful IPO in September 2018 valuing the company at well north of $2 billion. Prior to building Eventbrite, Kevin co-founded Xoom, the money remittance business, in 2001, and he served as CEO until 2005. Zoom also had a successful IPO before being acquired in 2015 by PayPal for about a billion dollars. Kevin's been a very successful investor as well. Some of his most successful early stage investments include Airbnb, Pinterest, Trulia, Skybox Imaging and NewFront Insurance which we talk a bit about in this episode. Kevin was also a partner at Founders Fund. In this episode, we mainly talk about Kevin’s journey in creating and building Eventbrite, including the spark behind Eventbrite in creating user experiences, the secret to making successful acquisitions and how to navigate being married to your co-founder. Episode Highlights: 2:36: What was the spark for Eventbrite? 5:11: How is Eventbrite used to create live experiences? 6:12: What are the benefits of a platform? 7:49: Are there things you did early on so that the platform could thrive? 8:34: Looking back, is there anything that you would have done differently or re-prioritized that would have allowed you to move quicker? 10:11 What do you look for in a great hire? Anything to avoid? 12:46. Eventbrite is well known for its organic user adoption. Is that something that you planned? How can other companies learn from your success? 14:35: How do you get the right fit? 16:19: How do you keep a leg up on the competition? 17:43: Has starting a company with your spouse given you added perspective about how to evaluate teams and how they interact with each other? 20:27 How much time do you spend on what competition is doing? Should founders get hyper focused on entrenched competition? 32:49 What are some of the rules of the road for making acquisitions? 24.52: What other benefits have you had as a business builder from being an investor? 26:13: Tell us about New Front Insurance, a new company that you’ve just invested in 28:03: What is your favorite book to recommend to entrepreneurs 29:13: What's something that you believe that isn't conventional at most others don't believe 30:15: What's one thing you wish you could go back and tell yourself when you were just getting started as a founder.

Tom has worn many hats in his time at BitSight, including EVP of Sales and Marketing, COO and CEO. In this episode, he walks us through how to navigate relationships with founders as an incoming CEO, how to use content marketing in an enterprise market, and how to think about go-to-market strategy for a global business. Tom Turner is CEO and President of BitSight. Tom has extensive security industry experience, and has helped build category-defining companies. Prior to joining BitSight, Tom was a founding member of the executive management team of IBM Security Systems, a new division within IBM Software group that was created on the heels of the Q1 Labs acquisition. Formerly, he was Senior Vice President of Marketing and Channels at Q1 Labs. Before joining Q1 Labs, he served as Director of Marketing for endpoint security at Cisco Systems. Tom also served as VP of Marketing at Okena, Inc., where he helped pioneer the intrusion prevention market and led the company to its successful acquisition by Cisco.   1:36 Tell us about your company 2:17 How did you become the CEO at BitSight? 4:34 What is it like to be a CEO of a business where the founders are very engaged with the company? 5:52 How do you manage instances where you disagree with the founders? 7:06 Tell us a bit more about your choice to take on the VP of Sales role during a transition in leadership 9:32 What is it like to find enterprise sales talent in the Boston market? 12:00 What is it like to be in a business where you have to create a new market? 13:41 How do you find the ideal profile of a customer for your product? 14:57 How should a founder or CEO think about marketing spend for a new enterprise product? 16:30 Tell us about your decision to host a customer conference and how do you measure its success? 18:55 In thinking about your go-to-market strategy, how did you decide between selling to large companies versus mid-market customers? 22:31 How are the support models different for the two types of customers? 23:49 What are the challenges in being a globally distributed company? 27:01 What did you learn about fundraising for a rapidly scaling company? 30:06 What is your favorite book or piece of content that would be useful to our listeners? 31:11 Who is a founder or business executive that you respect and why? 32:05 What’s something you believe that other’s generally don’t?

This week we are joined by Caryn Marooney for a salon episode that focuses on PR and communications. Caryn shares tips on how to build a brand, when to take PR in house, and how to handle a publicity crisis. Caryn leads global communications for Facebook and its family of apps including Instagram, Messenger, WhatsApp and Oculus. Prior to joining Facebook in 2011, Caryn co-founded OutCast Communications, one of Silicon Valley's premier technology communications firms. As co-founder, partner and CEO, Caryn was responsible for planning and executing communications strategies for companies of every size, including Amazon, Netflix, Salesforce and VMware. Caryn was named to the board of directors of Zendesk in 2014. She is originally from New York City and holds a bachelor’s degree from Cornell University. Highlights from the episode: 2:29 What was the biggest challenge that you saw startups facing with respect to communications? What types of pain points did you see them encounter most frequently? 3:22 What should startups focus on first when it comes to letting the outside world know they exist? 5:00 What process do you recommend founders go through to define brand and communicate company values? 7:10 How prescriptive should a founder be about their brand versus letting it evolve?  9:03 Can a brand get away with different brand personalities or does it need to consolidate around one identity? 9:53 How do you get attention from the press? How do outside PR firms help with that? 12:26 How do you vet if a PR firm is good and how do you get the most value out of working with one? 16:07 If you don’t have a significant “mic-drop” moment to launch a product, should you avoid PR altogether? 17:01 At what point should they bring a PR function in-house? 18:58 How do you ensure you get enough attention from your agency? 24:44 Tell us about the REBS model and give a example of messages or communications that fit the model well 24:37 Does a company’s communications strategy change as it grows? 26:56 In times of crisis, how do you handle PR? 29:02 Should founders seek marketing and communications executives for their boards? 30:59 What is your favorite tagline or slogan from a tech company? 31:35 What’s a book you’d recommend to founders in your area of expertise? 32:08 What’s something that you believe that most others don’t?

Pandora Founder and former-CEO, Tim Westergren, joins Founder Real Talk to reminisce on how his experiences playing in a band prepared him for running a company. From the first moment of product-market fit, to the right partnership that doubled growth rates, Tim shares the ups and downs of his 18-year journey with the company.  Tim started the popular personalized radio service in 2000 with the Music Genome Project. In addition to Pandora, he is an award-winning composer and accomplished musician with 20 years of experience in the music industry – spanning production, audio engineering, film scoring and live performance. Presently, he works extensively with technology partners, distribution partners, advertisers and investors to help shape the future of Pandora and personalized radio. Highlights from the episode: 1:57 How did being in a band prepare you for starting and running a company? 3:02 How did you motivate the team in a challenging fundraising environment? 5:40 How did you find conviction in the product before it was proven in the market? 8:39 How did you switch business models? 11:44 How did you deal with skeptics and disbelievers inside the company? 14:13 How did you deal with the regulatory challenges of creating a new technology? 17:28 How did you leverage the power of a grassroots community to grow the business? 19:20 What led you to the decision of bringing on an outside CEO? What characteristics do you look for? 21:46 How did you make the decision to support a new platform as a method of growth? 24:25 How did you manage the internal morale after a high fluctuation IPO? 26:21 How did you think about competition and what would you have done differently? 28:36 What is your favorite book or piece of content that you recommend to founders? 30:32 What’s one thing you believe that most others don’t? 30:51 What’s your favorite channel or favorite song to seed a channel on Pandora?

Serial entrepreneur and Color founder Elad Gil joins Founder Real Talk to share insights and his experiences in starting and building high growth start-ups. We talk about how a founder’s role changes over time, how to build a team that scales, and what conditions need to be in place for “high growth” to happen. His recent book “High Growth Handbook” is a must-read for any startup founder starting to scale up or hoping to get to that point one day. The book is also highly relevant for executives at high growth startups. Elad Gil is an entrepreneur, operating executive, and investor or advisor to private companies such as Airbnb, Coinbase, Checkr, Gusto, Instacart, OpenDoor, Pinterest, Square, Stripe, Wish, and others. He co-founded and is the Chairman of Color Genomics, and was its CEO until December 2016. Before that, he was the VP of Corporate Strategy at Twitter, where he also ran various product (Geo, Search) and other operational teams (M&A and corporate development). Elad joined Twitter via the acquisition of Mixer Labs, a company where he was co-founder and CEO. Mixer Labs ran GeoAPI, one of the early developer-centric platform infrastructure products. Elad spent many years at Google, where he started the mobile team and was involved in all aspects of getting that team up and running. He was involved with three acquisitions (including the Android team) and was the original Product Manager for Google Mobile Maps and other key mobile products. Elad received his Ph.D. from the Massachusetts Institute of Technology and has degrees in Mathematics and Biology from the University of California, San Diego. Highlights from the episode: 3:18 What is your definition of “high growth” and what does it look like when a company is in that stage? 5:32 What conditions must be met before a company reaches “high growth?” 7:06 What is the role of a founder/CEO in a high growth situation? How do CEO priorities change as the company scales? 9:03 How should a founder/CEO of a high growth company define “winning?” 10:36 What types of skills does a leader need to develop as the company scales? 12:14 Any tips for time management? 14:20 Is it important to have a chief of staff? What should someone look for in that role? 17:31 Do you think CEO coaches are helpful? Do you think mentors are helpful? 18:28 How do you know when to add a specific executive? Which executives should be priority hires? 19:19 What is the best way to ensure you’re hiring the right person? 22:45 How do you think about the tradeoff between functional expertise and culture fit in hiring for an executive position? 25:03 What is the role of an independent board member? What traits should you be looking for in this role? 27:23 How should a founder think about the process of looking for a CEO? 29:44 When thinking about financings, do you recommend founders accept capital before they reach defined milestones? What are the pros and cons? 32:11 What’s a favorite book or blog you recommend for founders? 32:44 Name a growth stage company you admire and why? 33:42 What piece of advice were you given as an entrepreneur that served you well?

Will gives an inside look at Stripe, one of the most valuable venture-backed startups in the U.S. In this episode, he talks about Stripe’s developer-first ethos, how the company is expanding into international markets, and how to run a great board meeting. Will is the CFO at Stripe, where he leads Stripe’s financial operations, including economic strategy, business forecasting, financial planning and analysis, and treasury duties. Prior to Stripe, Will was a general partner at Thrive Capital, where he worked closely with internet businesses across all stages and geographies, particularly within software and e-commerce. He's also worked as a software developer and company founder.  Will holds degrees in mathematics from Harvard University and law from Yale. 1:10 Tell us about your background and what led you to join Stripe as CFO 4:35 What made Stripe an interesting company to join and where do you think the company is headed? 7:33 What was it like to join a team with two well-known founders? 9:45 How does the API business model drive value for the company? 12:17 How has the team built the business to focus on the developer and make sure the developer feels well served? 14:13 Do you have any stories where something in the developer community didn’t go quite as planned? How do you get ahead of issues so they don’t become bigger issues down the line? 16:12 What are some tactics to drive loyalty with developers? 17:02 How do you balance working with customers of all sizes, ranging from startups to big companies? What challenges does that create? 20:50 How does the company think about capturing the global market? 21:58 What tactics does the company use to spur international growth? 27:27 What are concerns for a CFO of a company that has achieved high valuations? How do you manage investor expectations? 30:50 What book do you recommend to founders and executives of high growth companies? 32:19 What makes for a really great board meeting? 34:30 Who is a mentor that has helped you in your career and how might others think about how they can recruit a mentor?