What if I were to tell you that OKRs were for losers? What?! Well, not OKRs specifically, but having a goal itself. A goal is something you do now with the hope of a future payoff. The problem with goals, absent of having a system to achieve those goals, is that it is insufficient and puts you in a continuous state of failure. Either you haven’t achieved the goal yet, so you feel crappy, or you do and since you achieved it, you lose your single source of motivation -- the big letdown as they call it in sports. A goal person would say, I want to lose 20 pounds. A systems person would do 30 minutes of cardio and 45 minutes of weight training 5 days a week. The goal person hopes they hit their goal but feels terrible every day. The systems person makes being healthy a part of their lives and achieves something beyond a periodic goal, a lifetime of success. Systems done regularly increases the odds of your happiness in the long run.  

Most successful people are systems-oriented. Think of yourself. Sure you might have had a goal to work at a hot startup, but you built a system to get here. You studied hard, got good grades, went to a great school, acquired an in-demand skill, and made yourself attractive to a recruiter, and found your way here. That’s a system.

Or think about our company. A goal would be to say we want to be the most customer-centric company in our market. But a better way would be to build a system. For instance, a good system could be that we’ll always talk to customers ahead of actually building products and recruit them to be design partners. This way we know we’ll have a customer at the end of our development process and also they’ll be understanding if our product is a work in progress. Then we’ll work closely with them in developing it, with our engineers talking directly to theirs. That gives customer exposure and connectivity to groups within our companies that normally do not get much of it. Engineers working first-hand with our customers drive increased customer-centricity. Lastly, through those efforts, we’ll have a customer who will feel more bought in the creation of the product and therefore more inclined to work with us and purchase our product. 

So the next time we talk about a specific goal, please accompany that with your system to achieve those goals. Let's start building this muscle memory more broadly within the company. I'm sure it'll have a profound effect.

Systems over goals isn’t a new concept, but something I recently reflected on when reading this book, How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life, by Scott Adams. There’s a lot of great nuggets of life lessons in the book, including this one. Hope you find it as useful as I did and use those lessons at work and in your own lives.

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What they are good for, however, is taking time to pause along the long startup journey and reflect on all of the great progress made, and to say thanks to all of our wonderful customers and team. 

I’m truly excited that we’re building a fairer financial system and creating the infrastructure that will help level the playing field for the 80M people in the US who are unbanked or underbanked. You can read about all of the great progress we’ve made at Pinwheel here.

Lastly, I’d like to thank each one of the great people on our team that makes Pinwheel special. Thank you…

...Robby Abaya, Alex Antihi, Anish Basu, Tess Bloch, Andy Chen, Elena Churilova, Bridget Condie, Lauren Crossett, David Daudelin, Abby Feehan, Ben Foster, Arianna Gelwicks, Denisse Garcia, Dani Goland, Nicolas Gramlich, Stacy Hirst, Phil Jen, Steve Kekacs, Sam Kotlove, Alen Kubati, Jeremy Lee, Kurt Lin, Caroline Lo, Dias Marat, Bobby Mareddy, Kate Marienthal, Joey O’Donnell, Peter Oh, Aaron Pelz, Joseph Perry, Sasha Pilch, Octavio Roscioli, Brett Sheingold, Cameron Spiller, Kelly Steele, Steven Stone, Christina Wang, Alex Wendland, Matt West, and David White.

Much love and appreciation,

Curtis

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Many tech startups are founded by two people — a technical person (i.e. the CTO) and a business person (i.e. the CEO). Jobs and Wozniak are the archetypical pairing most think about. There are obviously varying degrees of technical competence, but the CTO at their core knows how to build. It’s a clear undisputed demarcation of qualifying for the role. If you don’t know how to build, you can’t be the CTO. To assume the role, the CTO had to undertake, in most cases, years of training through a combination of theoretical and practical experience and prove themselves capable. You can’t fake code. 

Contrast that to the CEO. Since most can’t code, the CEO is often made CEO by default. They’re expected to handle all of the other things, which at a young startup, is a bunch of miscellaneous tasks — incorporating the company, managing orders, talking to customers, diligencing the market, etc., while the better CEOs have other special skills they can utilize from their prior experience such as product design, UX, etc. 

One role is based on their ability to do or know something whereas the other is based on their ability to NOT do or know something. And it is the latter person whose role is most important; the person who is the ultimate decision maker. Sounds crazy, right?! Yet this is the case with many companies. 

So if you’re the CEO I described, are you a complete fraud? 

Well maybe…but here’s the secret. No one teaches you how to become a CEO. There’s no CEO degree you can get. You can only learn by being in the role. So how do you become a great first-time CEO? Here are some thoughts from my time being one and observing others:

1. “I know that I know nothing.” -Socrates. By far the biggest piece of advice is to be humble. Nothing else will work unless you accept that like Socrates, you know nothing. If you’re not humble, you won’t feel as strong of a desire to get better. You’ll be overconfident and more likely to continue making mistakes. Your brashness won’t engender respect from your team or cofounder. Your belief that the CEO title makes you the boss, will make it hard for you to trust others. Having the title of CEO doesn’t mean shit. 

2. Know the rules of the game. Break down the responsibilities of a CEO like a set of skills to masters. Being an effective CEO is a combination of decision making, data analysis, communication (written and verbal), sales, strategy, product, UX, recruiting, and management. Make no mistake, these are skills just as data structures, algorithms, and software design are for an engineer. 

3. Learn quickly. If you recognize that you don’t know shit, the difference between the people who sink vs. swim is those who have a deep thirst for self-improvement and a desire to learn. They know their shortcomings and constantly find ways to improve themselves. They talk to experts, they learn from peers, they read, take courses, study the masters (Bezos, Jobs, Collisons). They’re voracious learners.

4. Get experience. The fastest path to learning is by doing, but inevitably, you’re going to screw up a lot. That’s ok, so long as it’s not a fatal mistake. Continue to do, reassess, and assuming you’re humble and a quick learner, you’re going to get better. Better yet, get some experience before jumping into entrepreneurship. It goes against the romantic narrative of dropping out of school and becoming an entrepreneur, but the best founders have a fair amount of experience and just as important, a deep network of people they can recruit from their prior companies.

5. Work harder. What you can’t make up in skill and experience, in an early stage startup, you can compensate partially by sheer work ethic. You’re qualifying leads, reaching out to candidates, talking to customers, etc. Hustle can go a long way.

6. Hire people better than you. Again, if you’re humble, you’ll realize that you don’t have to make every single decision. In fact, the activity that gives you the most leverage is recruiting. Hire people who are better than you at the specific set of activities they specialize in and let them serve as your teachers. You get the triple benefit of improving the overall company, learning, and giving you time back to work on other things. Unblock them and get the hell out of their way. This piece of advice also applies to your role. If the time ever comes when you need to replace yourself for the betterment of the company, understand the rules apply to you just as it does the engineering manager you hired.

7. Create value for the company. Especially early on at a company, being a “company builder” holds very little value. Instead, pick a lane where you can add tangible value. Sales, BD, Product, Marketing, etc. Learn to have a specialty. The side benefit is by keeping busy adding value, you’ll be less of a distraction to others, as my mom says, idle hands are the devil’s workshop. 

8. Get an executive coach. One of the biggest regrets most founders have in retrospect is not investing in an executive coach. I understand that this can seem like a luxury that most companies can’t afford early on, but if it means your team can perform twice as better, it’s well worth the investment. These days it’s easy to find a great coach on sites like Sounding Board. If you can’t afford a coach, an alternative is to find a group of peers to lean on and use as a sounding board. Not only will it help you with explicit tactics, but sharing in your struggles will also relieve a lot of the loneliness you feel as you realize everyone has the same issues.

9. 2 ears, 1 mouth. An obvious tell of an inexperienced CEO is their inclination to always want to speak and be the authoritative voice. Wrong! Leaders listen, they have awareness. They know the real job of a CEO is to serve, not to be the one ordering people around. If you thought being CEO was being the boss, pick a new profession. 

10. Be a good and decent human first. Whether you know it or not, as CEO you set the culture with your behavior. If you’re callous and rude, or lack integrity, your team will follow suit. If you focus on performance and set a high bar, your team will follow suit. If you focus on diversity and inclusion, your team will follow suit. Get the picture. The thing about culture is that it compounds and hardens over time. So be judicious and intentional. 

This list could have been over 100 bullet points, but these were the ones that I thought were most relevant. What other ones could you think of? I’d be curious to know. Let me know in the comments below. Thanks!

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Today, I went to put on my boots and found my son’s Hot Wheels car snuck deep inside. Earlier in the week, in the few minutes between work calls, we were playing cars on his racing track and afterward, he put the car in my boot to remind me to play with him again soon. The bright shining light in an otherwise dreary year has been these precious moments. Spending time with my kids -- a few minutes between calls, the occasional lunch dates, early dinners together all made possible because we’re all working from home. 

Recently my mom showed me a picture of me when I was four years old and she told me fondly that while money was tight during that time, it was the happiest she’s ever been. She then reminded me, that my son is the same age as I was in the photo and how I should be so lucky and appreciative now. Lockdown has given all of us this gift, but lately, I’ve been wondering if it will be a flash in the pan or will it drive meaningful change and force us to rethink and reprioritize what’s important. With wide distribution of vaccines nearing and “normal” life around the corner, I wonder how my life and the lives of so many other people will change when we return.

To be honest, I’m not entirely sure. But one thing for certain, years from now, when my kids are grown adults, I’ll always think back fondly on this period and the time when my son wanted to play cars. What will you think about years from now?

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I recently jumped on the bandwagon and took the opportunity of low interest rates to refinance my mortgage. I didn’t expect an easy process but thought it’d be less work because we were using our existing mortgage lender. However, it was far from it, it was painful. They reasked for everything: employment offer letter (hard to obtain when you founded your own business), W2, paystub, bank statements, tax filings, ownership in my company, and insurance information. The total came out to 68 items! And the worst part might have been the secured email portal my bank was using, which required me to login and tediously download and upload documents and send correspondence. Every. Single. Time.

Ultimately, we got our house refinanced, but the end-to-end process of five painful months was frustrating. It was a good thing interest rates continued to stay flat or drop, had the Fed decided to increase interest rates, the lengthy period would have been real dollars lost. 

What was even more unsettling, was the process of my bank verifying that I worked at the company I founded: 

Bank Agent: “Our verification team is having a hard time contacting your HR from Pinwheel, would you be able to provide a verifiable company contact number for your HR, so we can get the employment verification completed.”

I provided them with the email of our Head of Ops

Bank Agent:“Hi, would you be able to provide the contact information, I will have to submit it to the call team which is a third party that will perform the call verification”

Me: “Hi, I have provided you with their email address but let me know if you need me to send again”

Bank Agent: “We need their phone number. We can only verify by calling them.”

Talk about not being very secure or easily gamed. The current system is antiquated and not optimized to handle today’s consumers.

In contrast, Pinwheel’s Income and Employment Data products link your payroll data directly to the lender, through an API, providing employment verification and income data such as paystub history and wages earned. Pinwheel eliminates the need to download and upload numerous documents to an antiquated web portal or provide the phone number of someone at your company to verify your employment. Instead, this “source-of-truth” information is seamlessly verified by you leveraging your existing payroll or employer credentials so you can transact faster and more securely, speeding transactions in time-sensitive situations like refinancing a mortgage. The benefits extend to companies too. Because everything is done programmatically and without having a middleman, our service saves many hours of manual verification time. 

If your company would like access to our Income and Employment API, shoot me a note or reach out to sales@getpinwheel.com.

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I’ve been playing Madden for many years. For those who don’t play, each player is given skill attributes such as speed, agility, and strength that parallels their real-life abilities. Awareness, however, is the attribute that most reflects how great of a player is. In Madden terms, how quickly they adapt to their surroundings. Take seven-time Super Bowl champ, Tom Brady as an example. His physical attributes are middle of the pack to below average, but his awareness score is 98, best amongst all QBs. 

In real life, awareness is just as important as it is in a videogame to your success, particularly the more senior you are at your company. When you’re an individual contributor, you’re aware of all of the small details, how long each project takes, and the harmful effects of thrash (because you’re doing the work!). But the more senior you become, the more susceptible you are to losing awareness of what’s really going on at a company. You don't receive regular feedback from a manager -- after all, no one tells the Emperor they aren’t wearing clothes, you’re not spending as much time in the weeds, and therefore when you direct people, it can feel ungrounded in truths and can completely miss the mark. 

In my experience, the best leaders have a high awareness of their situation and team. They know when to press, when to give the team time to breathe, and understand that even an off-handed comment can sometimes have company-reaching ramifications. They are best at managing their own psychology, per Ben Horowitz or at least pretending to do so. 

When I was running Luxe, I remember how brutal our series B fundraise went. I did so many investor pitches (over 100) that I was basically living on Sand Hill Road and South Park. Since the team saw that I was missing most of the day, they naturally knew I was fundraising which would always be super awkward whenever I would come back into the office -- sometimes to a standing ovation -- expecting good news, only to hear from me that we got rejected again. If I weren’t aware of the team’s reading of my body language, words, and emotions, I would have let my depression get the best of me and I would have lost the team. Being aware saved the company.

On the opposite end, the worst leaders are those that mix a lack of awareness with self-centered behavior. The ones who are unwilling to deal with their emotions that they end up actualizing and sharing their insecurities and anxieties with others. It comes in the form of lashing out or creating unnecessary work to make themselves look or feel better at the team’s expense. We’ve all worked with these types of folks. My advice is when you see this to let them know. Chances are they’re too unaware to know otherwise.

While direct deposits are a win for banks, what’s in it for the consumer to switch? Lately, a lot! With the rise of neobanks like Chime and Green Dot offering a mobile-first product with fewer-to-no fees, higher yields on savings, protection against onerous overdraft fees, and early cash advancement on wages, there’s a lot to like. Unfortunately, the act of switching direct deposits is manual and painful. 

While competition in banking has driven an uptick in technological innovation and product quality, direct deposit switching has remained largely the same as when it was launched (back about 50 years ago). Switching often means filling out physical paperwork that must be submitted via snail mail, is plagued by long wait times, and can require submitting multiple requests to be successful. In some cases, employees must manually submit through their HR department -- an activity that often gets deprioritized. All in all, it can be a months-long tedious process, a key reason why consumers are hesitant to move their funds and tend to stay with the same bank for an average of 16 years. Exhibit A: the form Chime sent me when I opened up an account.

Exhibit A: Chime direct deposit form

Fortunately, there is a better way. Through Pinwheel’s Direct Deposit Switching (DDS) product, we can programmatically switch your deposit to a new bank of your choice via our API. It’s fast, easy, safe, and efficient for consumers to automatically switch their direct deposit institution in just a few clicks. Simply search for your employer or payroll provider, specify the amount to be deposited, log in to your account, and request to switch (see Exhibit B). Our banking customers require a simple integration with our API to enable these capabilities in their app. 

Exhibit B: Pinwheel DDS user flow

Not only does it rapidly expand a bank’s profitable customer base, but it also gives consumers visibility and control over the allocation of their deposits. Additionally, companies no longer have to deal with the burden of employee requests related to switching. It’s a rare win-win-win. If you’re interested in learning more, check us out at Pinwheel or email me at curtis at getpinwheel dot com. And if not, still enjoy this great song by Jay-Z + JT with this blog’s namesake.

I spoke from a place of privilege. Many parents don’t have my options. They have to make tough decisions and live with the lingering guilt that lives on the other side of those decisions.

It’s worth acknowledging and appreciating. Thank you!

The depiction of success in our society is pretty universal -- some heroic achievement that leads to wealth, fame, or some other form of recognition. You see it in what the media covers, the entrepreneurs, the executives, athletes, celebrities, etc. But behind that success is a lot of hard work and sacrifice, specifically in the form of time that could have been spent with your loved ones. Timmy’s missed soccer game, Alice’s play you promised to attend but couldn’t, or more insidiously the physically present, but not mentally present moments you frequently have during family time. It all has me wondering if the cost of these “successful” people was all worth it.

When I founded Luxe, my first company, I wasn’t married, didn’t have any kids. And while I did eventually get married and had my first kid towards the tail end of my journey at the company, I never fully operated as a family man. Instead, staying in the same intense mode through the sale of the company to Volvo. I bore the daily scorn of my wife, who commented to me about being an absentee father and husband, who was infrequently physically present and even more rarely mentally. It was only after I was at Volvo did I start to recognize the folly of my life. Spending time with my son and then seeing my daughter born, changed my life. What was the point of wealth and fame if I didn’t have a family to share in its glory? What’s the point of being “that” person if your kids never see you? Is that even success? What’s your true legacy then? It was eye-opening!

Having seen my anxiety at full-force during my startup days, my wife asked me ever so nicely, that I never do one again. The stress of startups was terrible for my health, but also extremely taxing on her and the family. There was some pushback, but I agreed with a compromise. I could start and advise companies, but I wouldn’t ever be its CEO again. That seemed like a fair trade. So of course in that same year, I started my second company -- Pinwheel. This time, however, I wouldn’t be its CEO, leaving those responsibilities to a very capable former colleague of mine. And while since its founding, I have come back to the company in a full-time operating role (more on this sometime later), I have stayed true to my word and have come back as President and Exec Chairman. While that doesn’t seem too far off from the responsibilities of a CEO, it does feel different this time around. Partly due to the prioritization of my family, partly having a capable team at work, partly my maturation, and being a repeat founder. 

I do still struggle a lot with this balance between family and work. I wish more people talked openly about this. I’ve found that clearly blocking off time for certain activities and then being fully-immersed in those activities and nothing else is a good tactic. What are some others? 

Also, how do you balance the desire to be amazing at your job while also being an equally great parent and partner? How do you handle the guilt and feeling of inadequacy that is pervasive? Part of writing this blog is an exploration into this conflict. Come join in the discussion. Subscribe to the newsletter and come along for the journey.

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I have been talking to a number of friends and interview candidates about Pinwheel and while they conceptually understand our mission to create a fairer financial system, it isn’t until I explain to them that they fully grasp how large the scope of the problem we’re addressing and that it affects everyone, including them. 

Let me explain...

When you take out a loan, apply for a credit card or rent or purchase a home, a credit check is run in your name and the resulting output is a FICO score. Your credit score serves as the onramp to obtain any quality financial product. Even during the loan or mortgage underwriting process, when additional information is considered, a lender will first and foremost look at your credit score. 

Many Americans (nearly 40%) don’t even know their credit score and about a third don’t know what qualifies as a “good” credit score (670-739 is considered “good”, 740-799 is considered “very good” and above 800 is considered “excellent”). An even greater unknown for many is: what exactly goes into your credit score? 

• Personally Identifiable Information (PII): this includes your name, Social Security Number, address, employer, and date of birth

• Credit Accounts: This portion makes up the meat of your FICO score. All lenders from whom you have taken out a lending product (think credit card, auto loan, mortgage) report metrics such as total credit line and payment history to date.  

• Credit Inquiries: A list of everyone who has accessed your credit report within the last two years 

• Public Record and Collections: If you have overdue debt that was sent to collections or have filed for bankruptcy, that information will appear here. 

So, what’s missing? Your income - essentially your “revenue”, the item that dictates your ability to pay back the credit extended to you. Outside of the bank that receives your direct deposit, no other lender can automatically use your income in their underwriting process. Without that, lenders have to resort to approximation models based on piecing together imperfect demographic data. Whether it's buying your first home, getting a loan to cover an emergency medical expense, or buying a car to get you to and from work every day. Those are life-changing events, and they're too important to you to be contingent on a guess.

And that’s just the start. Because income isn’t included in your FICO score, you have to submit your pay stubs and employment verification entirely manually, a high-friction process subject to privacy breaches. This highly sensitive information often seems like it goes into a black box, leaving you with little control over your information or an understanding of your rate of borrowing. 

We exist to make this entire system more transparent and effective.

Through our API, we connect your employer’s payroll system to any application, from a lender to a financial institution to a savings application to...you name it. By easily making available income data and the systems to make payment directly from your paycheck, we can drive down APRs by significantly de-risking a loan, ultimately making a fairer financial system. 

If you’re interested in learning more, check us out at Pinwheel.

Writing about the two hardest things I know: Parenting and Entrepreneurship.

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