Pilot

Waseem Daher is the Co-founder and CEO of Pilot, the bookkeeping, CFO, and tax provider for startups and fast growing businesses. Prior to Pilot, Waseem and his co-founders Jeff and Jessica sold companies to Oracle and Dropbox. — Waseem, Jeff, and Jessica started Pilot in 2017, and have since raised over $160 million from investors like Index Ventures, Stripe, Sequoia, Whale Rock, Jeff Bezos, and over 40+ angel investors. — Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3FoYm52 — In this episode, we discuss: • Why Waseem’s building a startup that does your accounting • The reason he first started doing his own bookkeeping, and why he doesn’t recommend it to other founders • When startups should build something themselves and when to outsource • All the mistakes Waseem made building and selling his first two startups to Oracle and Dropbox • How to avoid “fake work” • How to get ROI from conferences • His disastrous first ever meeting with a VC • Why the best fundraising advice is to build a business that doesn’t need to raise money • “Companies are bought, not sold” and his framework for startup M&A • Why it’s a mistake to build your startup just to be acquired • Why consensus startup ideas rarely work, and the best startups need some secret or structural change that no one else has noticed yet • Why tech-enabled service businesses are so hard to scale • How Pilot got its first customers • Pilot’s unique approach to raising its Seed round • The initial scare when raising their Series A • Why its Series B was half of what they could have raised — Where to find Waseem: • Twitter: https://twitter.com/waseem • LinkedIn: https://www.linkedin.com/in/wdaher • Newsletter: https://waseem.substack.com/ — Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak — Production and distribution by: https://www.supermix.io — For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Waseem Daher

Founder and CEO

Pilot

On this episode Abadesi talks to Waseem Daher, founder and CEO of Pilot. Pilot is bringing bookkeeping into the modern age. He has started (and sold!) two other companies prior to Pilot. In this episode they talk about... The story of starting Pilot and what Waseem learned from his two previous companies “The end-to-end solution is really what made the business work. We are going to be your bookkeeper, your finance team, rather than sell you software.” The story of Pilot goes back to his first company, where they tried to do their books themselves, but realized how tedious it was and how much could be automated. He explains why he tries to have a more focused approach to company-building now: “I try to have a better sense of what is actually important. We were so worried about all of the stuff that we thought represented an existential threat but in practice literally zero of those things mattered. Of all the things I remember agonizing about, none of them had any actual effect on the business.” He also says that he makes sure to take time to rest and recharge, rather than working all the time: “In the first company we worked all the time, 6 days a week, 12 hours a day. Despite having worked that long, there were Saturdays where I still felt behind so I worked then as well, and every time I did that, it was always a mistake.” When it makes sense to take venture capital versus bootstrap a business “There’s a very pervasive and harmful narrative in Silicon Valley that the VC way is the only way to do it. I actually think the VC way is the unnecessarily difficult or hard way.” Waseem explains how to think about starting a company and talks about the principles to keep in mind when you’re thinking about the risk and reward of different approaches: “If your objective is wealth creation, you should not start a startup, you should go work on Wall Street or something. The easiest way to make $10M is to own 100% of a company that’s worth $10M, not to own 1% of a company that’s worth $1B.” He says that “lifestyle is not a bad word” and that as a founder you don’t need to care about serving a massive market unless you’ve taken venture capital funding. “Venture capital is not right for 99% of businesses. You have to be building something that is targeting a gigantic market to have a company worth billions of dollars doing hundreds of millions of dollars of revenue.” How to think about a potential acquisition “By raising a bunch of institutional capital, you’re prevented from taking exits that are otherwise very good or very profitable.” Waseem shares what he’s learned from two previous exits, one to Oracle and the other to Dropbox. He says that it’s most important to think about how you and your company will mesh with the acquirer and choose the offer that provides the best fit rather than the highest dollar amount. He says that if the fit is good, you will create much more value through the relationship together than the value of the acquisition. “Look at the acquisition as the start of a new relationship, not the end of something.” How Waseem stays productive He explains that he keeps most of his apps on his phone in folders rather than on his home screen. This creates friction and ensures that he has to be intentional about what exactly he is doing when he takes out his phone. He also explains exactly how to write emails that get responses from busy people: “Craft something that is really short, that is to the point, and that has a very crisp and clear call-to-action at the end of the email. Ideally the call-to-action is as easy to respond to as possible.” We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 😸

Waseem Daher

Founder and CEO

Pilot

Rachel Hepworth is VP of Marketing @ Pilot, the startup that offers the best bookkeeping, tax and CFO services for growing businesses. To date they have raised over $58M from some of the best in the business including Index Ventures, John Collison, Paul English, Drew Houston, Frederic Kerrest, Diane Greene and more incredible names. As for Rachel, prior to joining Pilot, she saw the hyper-growth of Slack firsthand enjoying a couple of different roles including Head of Growth Marketing and then also Head of Self Service and Platform Marketing. Before Slack, Rachel spent 4 years at LinkedIn where she led the product marketing team for content experiences. Finally, before LinkedIn, Rachel spent close to 3 years at Climate Corporation, prior to their $1Bn exit to Monsanto. In Today's Episode We Discuss: How Rachel made her way from marketing manager at Climate Corporation to VP of marketing at Pilot today? What were Rachel's biggest takeaways from her time seeing the hyper-growth at Slack? How does Rachel think about organic growth and inciting word of mouth today? How does Rachel think they can be more accurately tracked and measured? How does Rachel think about the optimal ratio of paid to organic in growth? Would Rachel agree in paid, your payback period doubles every $5M you spend? With the rise of product-led growth, are we seeing a fundamental shift in the structure of sales and marketing? How does Rachel see marketing move ever close to the function of customer success today? What is the optimal way for customer success and marketing to work together? How does Rachel think about the importance of getting in front of your customers? Why does Rachel believe that data tells you the what and customer conversations tell you the why? What is the right way to structure your customer conversations? Where do so many people go wrong here? Rachel's 60 Second SaaStr: Hardest element of your role with Pilot today? If Rachel could change one thing about SaaS today, what would it be? Who is killing it in SaaS marketing? Why? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Rachel Hepworth

Rachel Hepworth

VP of Marketing

Pilot

Waseem Daher is the Founder and CEO @ Pilot, the startup that takes care of your bookkeeping from start to finish so you can focus 100% on making your business succeed. To date, Waseem has raised over $58m in funding from some of the very best firms and people in the business including Index, Stripe, Okta's Frederic Kerrest, Gusto's Josh Reeves, Stripe's Patrick and John Collison and Lola's Paul English, just to name a few. As for Waseem, Pilot is the 3rd business he has founded with his co-founders, the first being Ksplice and the second Zulip, which was acquired by Dropbox in 2014. He has also enjoyed spells with the likes of Oracle and Dropbox in the interims. In Today's Episode You Will Learn: 1.) How Waseem made his way into the world of startups over 15 years ago and how that lead to his founding of Pilot today, changing the world of accounting? Does Waseem agree with Joel Fernandez at JoyMode that "serial entrepreneurship is overrated? What has Waseem done differently this time as a result of his 2 prior founding experiences? 2.) Why does Waseem believe that "passion is overrated when it comes to starting companies"? If passion is not fundamental, what does Waseem believe is fundamental to ensuring one sticks the course? How does Waseem think about the craft of company building as a passion in itself? 3.) What is it about Waseem's relationship with his 2 co-founders that makes it so successful for the third time around this time? What do they do to ensure that unity and trust remains? Where do they have weaknesses and flaws in the co-founding relationship as a result of it's maturity? What advice does Waseem give to newer co-founding partners? 4.) Waseem has previously said that "VC is overrated". What does he mean by this? How does Waseem think about the decision to bootstrap vs to raise VC? What are Waseem's biggest lessons when it comes to investor selection? How much of a role does brand play? What core questions should the founders ask the VC? 5.) What does Waseem mean when he says, "never sell your company"? What were his biggest lessons from exiting two companies to Oracle and Dropbox? How did it shape his thinking on M&A and exits? How has Waseem seen his role scale and develop as a leader and as CEO? What are the biggest challenges he has found in his personal scaling? Items Mentioned In Today's Show: Waseem's Fave Book: Harry Potter As always you can follow Harry, The Twenty Minute VC and Waseem on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Smart executives and business owners know that harnessing the power of AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike 's award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

Waseem Daher

Founder and CEO

Pilot