YouSaid · the spoken record

Daniel Yan

lines on the record: 44
first: 2022-07-01
most recent: 2022-07-01
sittings or episodes: 1
sources: podcast

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“Yeah, I mean, Checker will be a great HR tech software platform who continues to grow and innovate for customers, continues to drive our mission to build a fairer future and give second chances. I would hope that fair chance and second chance hiring, which is my passion, giving chances to people who've been in prison, becomes more mainstream. And for me personally, I guess I'll be a dad and family guy in 10 years from now, so that's going to be an interesting shift.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“So we did start having billboards in the bay area for the first time in the last year, and it's been great actually. I was just in New York, and there's just so many people there and so much going on. It would be great to have a billboard in downtown New York.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, there's definitely one. His name is Pascal Levigabua. He's actually my first Android investor, and he's helped us over the years all the time. And it's been eight years so far. So he's been the young son Kiera.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know if it's going to change. People have fun on Twitter and other places talking about those things, but sometimes it's just wasted opportunity for me. We have all of these resources and smart people are, there's so many problems in the world around environment and water and social and opportunity for people and all of those smart engineers are working on million dollar NFTs to sell. And I love Web3 and NFTs and I think it's the coolest technology and opportunity in the world. It's just the early applications are a little bit onwhelming.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“All of the entitlements around crypto and money and using super smart people and super cool engineering for the most stupid things ever.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“On my home office like a year ago, I started to invest into better equipment. And definitely my MacBook docking station, amazing, just saved me so much time”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, it's whatever current leader I'm hiring. I mean, right now I'm hiring for the head of revenue. And so it feels like the hardest to hire.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, lots of business books. I don't know if I have a favorite, but I'll share with you the latest I read that I like a lot. It's called Accelerate. It's a book about engineering and DevOps, but it's very readable by any non-technical people. And that's the first book that gave me the answer on how to measure engineering in a tech company. Because that's actually one of the hardest things to do and engineers push back on it. And that book was very clear on how to measure engineering quality and velocity in the best companies.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, they're standalone businesses. All of the MAs we've done was either standalone businesses or very small teams, which is easier to integrate, and then focusing, I think, on the culture is very important. I think most M&A fail because of cultural issues and kind of treating that people at the acquired companies not as well as your own company and forgetting about what it means to them. So in the last integration, we're doing rights now, we're trying to be very people first and very focused on the employee experience of the team being acquired. That's been helpful.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I think now we've bought five companies so far, so lots of learning along the way each time. And we just announced our biggest acquisition with hundreds of people recently. So at that scale, it's a lot of work. M&A's tricky is hard, there's more failure than success in M&A. Most companies buy others and it doesn't work out. For us, it's been pretty good. So far, we haven't bought companies that we had to deeply integrate the product and the platform. That's a very hard thing to do. So the suppliers were already integrated with us.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe if I can pinpoint one or two starting the company to be an API first, the way we did it, I think, was really good. And today it still differentiates us. So building an API, being an API first company, and being focused on the developers, that has been magical for us. Brought us so much growth, so differentiated, still helps us win today. Another one is we've done some pretty good M&A and acquisitions early on. We're a data company at Checker, and I decided earlier on to buy some of our data suppliers and supply chain, which was a non-obvious decision. And that has been a very good investment and move. So yeah, I would say those are two.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“There's no one to blame into it. It's just me, it's just strategy decision, and it's me at the end of the day. So no, that's fine. I think there was a good learning.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Very difficult, yes, and we still need a little bit, I would say, because once you have a multi-million dollar very big enterprise customer and they keep asking for more features and you keep not being able to do it for them, it's very hard because you don't want to have that churn and lose that big logo or that big revenue. So yes, very, very hard to retreat from it.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“The enterprise is just a completely different beast. I was naive in terms of how those customers think how little they understand tech and software and how you really have to adapt your entire product to them. So I was naive. There's just hundreds and hundreds of features and custom things that large enterprise customers want. And we're definitely not ready to push back on that and to build the right product for them. And also the sales process. Everything is way more expensive and harder. And so we got some wins, but it was so expensive in terms of sales.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“The worst decision for sure was to go too early into the enterprise. So after we had really good traction in the gig economy with tech companies, I read crossing the chasm, and so I decided, okay, let's expand to enterprise customers. And that was the worst decision I've made. I was super naive on what it takes to go enterprise. And so I think we lost a bunch of time and money and to go too early into very big enterprise customers who are not tech companies.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Happens, I think, in the early stage, it happens all the time. But I think as you start to get very late stage and raising money from New York investors and mutual funds, they're going to be a bit closer to judging you like public investments. The accuracy and the forecast and those things are becoming more important. So you just have to change your fundraising strategy a little bit. It's very different from a Series A where everyone knows that the projections are open to the right, but not guaranteed.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think it was our Series C hardest. I mean, overall, we've been lucky. I've had really fast, easy fundraises because the business we've been performing well and we have a good team. But the Series C was one of the hardest because we got the term sheet for the Series C and then our revenue slowed down a little bit. So we missed the quarter in terms of revenue targets compared to what we had in the CRC pitch. And the investors in the CREC started to get worried and we haven't closed around. So we actually had to negotiate very slightly some of the terms to get it back on track and close it. I'm grateful that the investors were flexible and friendly, but that was one that was harder.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, back to fundraising. I think the most important in fundraising is who you work with, so the quality of the investor. And so too many times founders focus on the number. And so the high valuation. And then you can end up raising very high money from low quality investors or hedge funds who might be too aggressive and not really help your company. So I think that's the most important is the quality of the investor. Not to overstress the dilution and the economics. You can use competition to negotiate. So overall, when you get multiple termsheets and investors, if you do some basic negotiation, you're going to get fair terms. But I think hiring, working with a good partner in investors is the most important. I've seen many situations where the investors backed down or backed off the company or didn't finish the deal because it was just a transaction or conversation. They were not attached to understanding the company's long-term potential.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I completely agree. I think you've got to be careful. There's many, many reasons why raising at too high evaluation is going to be a negative for your business. So all of those are fair points and you need to be able to justify valuation today and have a compelling story for new hires on how you're going to three, four, five X this valuation in the future.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Too high, and also to make sure we're always profitable or very close to profitability. Then you own your own destiny. If you're profitable, you can always keep pushing for a few more years and catch up to whatever valuation of the day your company is at.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I do a lot. We've been quite conservative on all of our fundraises. We rarely fundraised really too far ahead of our scale. We've always been a profitable business, which most companies are not. So actually, we're lucky to not push the valuation too high. We never fundraise that 30 to 100 times revenue multiples or things like that. We actually always had pretty reasonable, I would say, lower valuation than other companies. And we were very careful with the amount of money we raised. We have almost no burn and are profitable most of the time. So I've been more on the conservative type side of the spectrum. And I'm involved with many other startups and companies. I always try to coach them on not raising too much money and then being stuck running out of money and having to do a down round, which is a horrible situation. So I think the risk is high now, especially with the crazy valuations from the last year or two, but knock on wood. I think we check if we've been careful not to push the valuation.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so 2019, we're starting to get some business headwinds because we grew very fast in the gig economy and with tech customers and those companies like Uber, Dordash, and others went public at those days and started to suffer themselves. So that had a negative impact on our business. So business was starting to slow down and then COVID hit. And during COVID, hiring stopped in many businesses and had really impacted our business. So those were the hardest times of the company. We had to make layoffs. We had to change our strategy. We had low morale. It was hard. It was some of the hardest times. And that was actually a good thing if for high growth, confident company, that was actually the good shock that in a way we needed to update our strategy to change the product we do, to change some aspects of our culture”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, I didn't have too many. My personality is quite confident, maybe overconfident. So I'm on the other side of the spectrum, which definitely was helpful for starting the company, taking all of the risk I'm taking, pushing forward and making fast decisions. So for me, I'm usually pretty confident in myself, which helps me not feel pressure or things like that. I have other issues that confidence comes on the other side and conflict with humility or empathy being patient.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, that's a good question. I think I can be more efficient. Things we've done is we sent the board's information away ahead of time. All of the financials are already in the appendix, so we don't spend any time talking about those. And then we have debates mostly on products, strategy, go-to-market strategy, leadership structure, the topic you mentioned. So I think those are the right ones. It can be done efficiently, potentially in one hour or two. Board meetings do tend to drag more and more. But I think if you can have three, four hours, that's actually productive debates. You learn something out of it. The company makes progress after having strategic debates. That's a positive. And I would say that's rare. Many board meetings, it's not adding value. It's actually creating more burden and work for the leadership team and the CEOs.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“To be able to push back, to take some feedback, but also say, hey, from the five things I've heard today on the board, this is one or two that we're going to work on. And it's okay to ignore our pushback on a few other areas. You also have to put yourself in the shoes of the board member. Sometimes it can be really boring to go to three, four hour meetings, only reviewing dry financials. So I think keeping your boards interactions also fun and exciting and bring them in the fun of building the company is important to have an eye bond team. And also doing dinners and personal connection as well. So lots of similarities with managing the C-suites.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there are similarities with managing your leadership team and managing your board at the end of the day. It's also a team and a group of people who are here to work on the business and to help the business. So I think a few things. So first, it's important, I think, to be very transparent with the board, just share the truth, what's going well, and also what's not going well. You don't want to sugarcoat or have just a rosy picture of your company with the board that's going to create a divide of understanding of where the company is and actually create more pressure. I think the board can be scary for founders too. So sometimes you want to please your board and really take every feedback and ask immediately to heart and execute on it. But sometimes you might not be able to or it could be conflicting feedback or maybe not the best thing for the company. For me, a few years ago, there was pressure on financials, revenue growth, which is always going to be some type of pressure from the board who wants, of course, the company to perform better. So I think it's important for the founder to listen, but also”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's been the best thing in my life. It did change my life. I don't know if I would have made it that far without this help. So I absolutely recommend it to any CEO. I think it's the best investment you can make. Many people tell me that they don't have the time to spend time with the coach. I think that's BS because having a coach helps you better prioritize your time, be more effective as a leader. And then what type of coach? I've interviewed a bunch of ask for referrals. I think the best thing for me was to interview a bunch of coaches, ask them what type of leaders they work well with, share your weaknesses and areas to work on and test them. So I think doing some testing with a few different coaches might be the best way the personal fit is very important. So most of them are happy to do like trial session, one or two coaching sessions. I would encourage people to try different coaches and see the ones that's best for them.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, I can still improve on many things. So, first, all of those areas, even delegation, I've improved, but I still have a lot to go. I think I can improve more on being more inspiring as a leader, sharing more personal stories, on storytelling. I think those are important areas where as an engineer, I'm not very good at it naturally, so I really have to stretch myself and learn this. Better listen as well. You must still tend to have opinions and form my opinions quickly, so I have to be more patient and a better listener. So till those are summaries I'm working on.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“A friend to improve whether it's like a therapist in life or coach in a professional setting. I do think you need others to help you. Otherwise, it's almost impossible for a human to change their behavior without help.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“So, I've had two different CEO coach over the years. My current coach, I think we've been working together for two to three years now. So I've worked on a few things with her. I think what was the most helpful witness in a coach is to have an independent person who can go and collect unbiased feedback from your leaders, from your board, and then work with me on an action plan on actually how to make progress on the day today. Because it's easy to do a 360 and you have this kind of theoretical feedback, but then how are you going to change every day and who's going to keep you accountable that you're actually improving your behavior? So she's been very helpful, very explicit, has good experience, and she was able also to attend some meetings, so to be like a witness in the meeting and said, I see how you changed your delivery, what words you use, the way you behave, or even your physical appearance in the meeting, having someone hands-on with you is super helpful because no one can improve on their own. It's almost impossible, even if you're very self-aware.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so we do a little thing. So, when COVID started and we moved mostly to remote, we started doing daily stand-ups. So we have a 30 minute daily standup with my leadership team every single morning. So that's been very helpful to have that personal connection. I messaged thread with my leadership team where we text each other and share things. A lot of them non-work related. Like we share news about each other's family and what we do on the weekends and cooking things, all kinds of pictures from vacation.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so back to the leadership journey. And I used to hire lots of execs, not find a good fit, and then they would be a lot of leadership churn over time. And I think that's the case in many fast scaling startups. If you see lots of execs come and go and come and go. And I think during the pandemic in the last couple years, thanks to the help of my coach, something changed and we started to hire a good team. And so I didn't invest enough into team building, personal connection building, events outside of work and really getting to know each other at the personal level. And I think that's one of the most important things to keep leadership team happy together.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“That has been helpful at Checker. We've been generous and positive and helpful when we let someone go. And so that has helped us to keep good relationships even with people who are not here anymore.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“That's hard. I don't know if I'm any good at it. I think you just got a bit transparent and care for the person. After repeating multiple times the same feedback, hopefully it's not a surprise for the person. So I think you're going to have to increase over time the intensity and make it clear that this is becoming a big problem. I think it's too easy to just deliver it. You have to say no. This is becoming an important issue. So I think have clear feedback that gets stronger and stronger. And then when you get to the final decision, you just have to share it as is. And then I think what helps a lot for people is how you do the process after the announcement. Being generous on severance and pay, crafting the departing message together with the person so that it's positive, committing to helping them on reference call and to find another job. I think all of those little details on how you let the person go and how you support them and your fare during that process.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it is a little bit of the shit sandwich, but you don't have to be a sandwich, and you also don't have to sugarcoat it. I think you can say, hey, this was great, great delivery on this, great hire. I think one thing we can work on is attention to detail be closer to the customer. It doesn't have to be the sheet sandwich, but there's definitely that balance of positive and negative”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“So, I think there's two things. So, first, it's important to give feedback often. And I think I was worried about giving feedback because I had five to ten constructive pieces of feedback, which were mostly like negative feedback. And I knew in my gut that if I just keep sharing this negative feedback, the leader is not going to enjoy receiving that feedback. So then I would just not share it. What I do now is changing the ratio of like positive feedback to negative feedback. So always start with one, two, three things that actually the leader does well or has done well recently. So start with positive feedback and then at the end one thing that they can work on to improve or do better next time. And I think delivering feedback this way to leaders, but also to anyone in general works way better than just bombarding them with 10 things they could do better because that's just demotivating for anyone independent of your seniority.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so in the early days, I was following the Y Combinator playbook that says highest, low, fire, fast. So I did fire fast many people, maybe too fast, I think. I was too fast to pull the trigger and let people go. You do need to give them some time. So founders, I would say, suck at giving feedback. There's many reasons why for some days it's hard to give constructive feedback to senior leaders, but you do need to give them feedback to talk about it with them and to give them, I don't know, I would say three to six months is a good period of time to try to course correct. And then if it doesn't work out, you have to have that hard conversation. So it's hard. It's a balance. You don't want to be too fast, so you don't give anyone a chance and you don't learn through the process. But you also don't want to let it drag for a year, which will really impact your culture and your company performance.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so first I would say some of the best leaders are the leaders who might not have the most amazing resumes or companies in the past, the ones that are really smart, hungry, wanting to get their big success in tech. So those can be some of the best talents that can be underrated. I think you have to hire them for what you need in the next two years. So if you look at the scale that they've operated at and you project yourself one or two years in the future, let's say if you have a hundred people in the revenue team and you plan to be two to three hundred in the next three years, we have someone who has experience at two three four hundred people. I wouldn't hire someone who's led a 2,000 revenue org per person. There's going to be risk there, especially if they haven't done smaller scale or startups in a while.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, the way I see it is so there are large scale executives who have scale teams with hundreds or thousands of people when you're in a company like this, what you do day to day is very different. You have a lot of other senior leaders, you do a lot of planning, you do a lot of delegation, you're quite far from the day-to-day, the customers, the spreadsheets, the calls, et cetera. If you have to go from that to then a very chaotic environment where there's no infrastructure, no team, no process, nothing, and you have to get your hand dirty and make the first documents and spreadsheets and all of the hires yourself by hand. Some people can do it, but it's really a shock to the system. And for most leaders, they realize it's just not the best skill set match for them because they've perfected the way to operate at scale. It can also be related to ego sometimes, like when people are used to having a huge staff with chief of staff and EA and all kinds of bench and direct the team and only do like reviews, getting back to doing everything yourself, not”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, lots of common problems. So, first, it's normal that leadership hires don't work out between one and two and one in four executive don't really work out in any company. So it is just a very hard thing to nail and you can never be 100% in hiring leaders. I mean, it's just hard because you only spend a few hours to evaluate someone and then you're going to have to work with them for thousands of hours. So it's just a flawed process in general. For me, the common reasons, one is oftentimes you are attracted by this shiny resume, really amazing experience and pedigree of the person. And because the person's background and experience is so exciting at some of the best companies, you might overlook some of the other gaps or flags that might not make this person the best for your company. For me, one thing that I overlook to many times is we have a core value checker of humility and sometimes I've compromised on that and hired some people that had a bit too much ego, I think. And that led to”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I made every mistake in the book. I think I hired over 20 plus, I kind of stopped counting leaders over time that didn't work out for one reason or another after some time.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, absolutely. Everything can be delegated. But in the early days, there's always going to be some gaps in your startup, right? You might not have a head of sales or head of product or recruiting team. So you can go push hard in the areas where there's no coverage. The best thing you can do is hire someone. So I completely agree that the highest leverage activities you can do as a founder is hiring the best bench and C-suite and VPs you can, setting the vision. That's only something you can do, finding the values and the purpose of the company or mission, being the cheerleader of the company in the media, fundraising. Those are some of the highest leverage activities only the founder OCO can do. Also spending time with customers is very important and I don't think you should delegate all of that. Founders should stay close to the customer.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I would agree that first I found this socket. I sucked at it a lot. I might still do. So it took me a while to learn how to delegate because like a founder, you want to make sure everything's perfect and good and I have a high bar. So I think for many years, I was very bad at it. I think you have to force yourself to do it as a founder. There's so much you can say about the person everything, but I think for many founders like me, I have to hearing the feedback that this is not going to scale. I have to prioritize other things. I had to force myself to let go of some areas. I think one thing that helps is to then focus my mind on other things. So if you can focus your mind on other bigger problems that only the founder can work on, like finding new types of customers or launching a new product or fundraising, those are activities that only the founder can do. So for me, it does help myself to focus on other projects so I can delegate more of the day-to-day.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source
“It all started in my living room with my friend Jonathan, co-founder and engineer, were hacking, coding, different side projects, and one of them was the early version of Checker. We had many startup ideas that we're playing with, but this one came from our previous job, like many B2B startups. You might find problem or a gap in your work and then you had to build something better. Jonathan and I were both engineers on demand delivery startup and the startups was hiring lots of contractors. We were looking at the background check process. That was a bottleneck to hire people fast and with a good experience. And after looking at the options on the market, we realized there was a gap and no great solution. So we said, hey, I think we can build something better here.”
2022-07-01 · The Twenty Minute VC · 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan · IDENTIFIED FROM THE TRANSCRIPT · source