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- Tips from a $18B Founder, Fix These Four Communication Problems - Tactician: #00130
Tips from a $18B Founder, Fix These Four Communication Problems - Tactician: #00130
How AI Will Create More Successful Founders

So, an $18B founder’s tip on company culture is ‘Free snacks!’
Because nothing says ‘I care’ like unlimited pretzels.
Tips from a $18B Founder
Why Read:
This article provides valuable insights from a founder who built a $18B public company on branding, culture, operations, and maintaining a long-term perspective.
Featuring:
Logan Bartlett (@loganbartlett), Managing Director at Redpoint interviews Vlad Tenev (@vladtenev), Co-Founder at Robinhood
Link:
Key Concepts and Tactics:
The Importance of a Memorable and Polarizing Brand Name:
"When we came up with the name Robin Hood, and we presented it to the team, we had some people threaten to quit. They were like, we hate the name. The entire business model is going to involve serving lots and lots of customers, but we don't want to scare off the wealthy people because if you look at economics of a financial services company, they tend to be concentrated in wealthier people."
"Our thoughts on that at the time was… we both really loved it… And so, our thoughts were that if the name elicited strong reactions, even if they weren't all positive, at least it would be memorable."
Maintaining Authenticity and Transparency in Communications:
"What I learned is that you have to rip up the talking points once you know what you want to say and just speak authentically. When I actually said what I, when I say what I feel and what I want to say, not what is expected of me, I think it comes across much better."
Embracing Decentralized Product and Business Unit Ownership:
"What we gained is the GMs live and breathe the products. They care about the PNL. They're super accountable and they feel a ton of pressure over the entire success of the business including the PNL and that just wasn't the same in the functional structure."
"The downside is then there's tension and conflict between the platform teams and the GMs, which oftentimes fall on me to mitigate, but at least those are conscious conflicts that by and large make the company better because sometimes GMs want to move fast and be independent and the design team will say, hold on, like what you're doing is not consistent with what the brokerage team or the credit card team is doing, so we'll have to slow down and kind of redo that."
Rigorous Financial Modeling and Experimentation:
"Finance obviously owns the financial model. Marketing owns the CAC to LTV calculations. But of course, finance kind of shakes hands and agrees on what the CAC and LTV actually are. They're the source of truth."
"We consciously, have variations: bear case, standard bull case, very bullish case. Typically the GMs look at the very bullish case and finance has to kind of keep them honest and look at the bear case."
Navigating the Shift to Remote Work and Returning to the Office:
"I was like, Oh God, I made a terrible mistake here. Uh, this is not, this is not good. I felt bad about it. Um, and then the, uh, the feedback I heard when we decided to go back into the office was not only has no other company managed to get their people back into the office successfully, While hedging and saying that we're not remote first, they didn't know anyone."
"Explaining the why of things is important. Um, I don't know a lot, a lot of people just have fear of doing it. I think, uh, you know, you, you talk to people that want their employees in person and I come across these entrepreneurs and I ask, well, What have you announced publicly and a lot of times they just aren't very direct."
Maintaining a Long-Term Perspective Amid Stock Price Volatility:
"I think what I found is most effective is to constantly remind people what the strategy is and make sure the strategy is supported by really exciting products that people can look forward to… I mean you you don't have to work very hard to convince people that if we execute on these things, and if they're as good as we believe we can make them, then that's going to transform the profile of the company and the value of the company should follow."
Fix These Four Communication Problems
Why Read:
This article provides critical lessons on effective communication for startup founders, highlighting common pitfalls to avoid and strategies to clearly convey information and build credibility.
Featuring:
Deborah Liu (@debliu_), Chief Executive Officer at Ancestry
Link:
Key Concepts and Tactics:
The Dangers of Poor Communication:
"Time and again, I've seen an otherwise amazing person be held back by their communication abilities. Some incredible strategists and executors have been hamstrung by their inability to distill and disseminate information."
"I learned this lesson early on. During my freshman year at Duke, I took the Intro to Engineering class taught by the famed professor Henry Petroski. He urged us to learn to communicate, not just do the work. He attributed some of the greatest engineering disasters to poor communication, not technical error, and that is a lesson that remains with me to this day."
Error 1: Providing Too Much Detail:
"I often tell my teams, 'If you're the one who's thinking about something 110% of the time, and you are asking me what to do, then we are both in the wrong jobs.' You spend most of your time immersed in the details, but your job is to take it up a level—and then take it up a level again."
"I spent many years struggling with this. I felt like I needed to show my work to prove my point. But this resulted in getting bogged down with charts and graphs while failing to convey the larger point."
Error 2: Using Excessive Jargon and "Inside Baseball":
"We often use acronyms and terminology (TPS reports, I'm looking at you) to make our own lives easier, but they end up making other people's lives harder. Things quickly become a game of jargon, reducing people to "insiders" and "outsiders.""
Error 3: Lack of Appropriate Context:
"I've written before about the importance of context for effective communication. Many executives spend maybe five percent of their time thinking about your specific area, so it's critical to make sure you are giving them the background they need."
"Every communication should have sufficient context, but not too much detail for anybody to pick it up and understand what you're talking about. Remember, presentations get forwarded. Strategies get passed around. Make sure that there is enough context that anyone seeing your work has a general sense of the environment in which the communication is shared."
Error 4: Ignoring Blind Spots:
"I have seen otherwise great strategies and presenters caught out for missing some data or not fully representing all points of view. These blind spots undermine credibility in the best case and can be disastrous in the worst case."
"Focus on communicating everything—both the good and the bad. Don't hide bad news; instead, make it clear that you see the full picture. Make your case, but also understand that there is a counterpoint to your strategy. Point out the flaws before someone else does, and take the opportunity to address their concerns before they are brought up."
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