There is a lot of discussion out there geared towards launching a successful startup, but not much guidance on how to successfully make the transition from founder to CEO. 

As the co-founder of LendUp and Mission Lane, On Deck Founders Fellowship alum Sasha Orloff is familiar with the process of making that transition. Now he’s founding his third startup in fintech, Puzzle.io, a modern accounting and financial insights hub, designed for founders and their finance teams. 

Recently, he took some time to chat with us on navigating the transition from founder to CEO, and the importance of discipline and accountability in ensuring his time and focus are spent entirely on high-impact functions. . 

Looking back a decade at the first company he founded, Sasha reflects on how different his life was. “I didn’t know what I was doing and I didn’t have kids — which meant lots of time to make mistakes.”

Without a family, he was able to throw himself fully into the grueling lifestyle of a CEO seven days a week. A 2006 study by Harvard Business Review which followed 27 CEOs found that they worked 79% of weekends and 70% of “vacation” days, on average. 

The stakes are different now, and Sasha can’t afford the risk of wasting time. He has a family that he needs to spend time with, and he also feels that he has more to achieve with this company than at any point before. “The ambition is bigger, but time is scarcer.” 

To meet his goals, he has to constantly ask himself if his time is structured in a way that allows him to accomplish the critical necessities.

As a result, Sasha  predetermines how many hours in a week are allocated to work, family, and himself so he can optimize his days and remove some of the mental burden of decision-making from the process. 

“Time is the coin of your life.. spend it wisely so that you get the most for your expenditure.” - Carl Sandburg

Time and energy are limited resources, and Sasha is vigilant about ensuring they achieve the maximum impact. 

A day in the life of CEO Sasha Orloff

Below is a look at the typical day in Sasha’s life according to the routine he’s built to support his efficacy as a CEO:

The snapshot above cover’s Sasha’s weekdays, but on weekends, Sasha is no less regimented: 

• His mornings are spent with his kids outdoors, either on a bike ride or a hike, or at one of their soccer games. 
• After that, he works half days from 1:00 PM until around 5:00 PM. 
• Then he and his wife might go out to dinner with friends or another social engagement in the evening. 

As you can deduce from his schedule, family and outdoor time are non-negotiable for Sasha. Being with family and being in nature are what helps him protect against burnout. 

He’s also sure to take a few vacations of one to two weeks every year plus impromptu powder days on the slopes, no matter how busy he is. “Everyone is susceptible to stress”, he acknowledges. “You can and should take vacations, unplug, recharge.” 

Embracing routine to minimize decision-making

Regimenting his free time in predictable patterns works best for Sasha because it frees his mental energy to focus on the highest-leverage tasks. He wears the same outfit every day for the same reason: a pair of jeans and whatever t-shirt is at the top of the pile. 

Meals, too, follow a familiar structure from week to week. Monday’s dinner is rice and a protein, Tuesday is taco night, Wednesday is pizza, Thursday is date night. Every day for lunch, Sasha gets a Sweetgreen salad. 

Why so much regularity? “I don’t have to spend 15 minutes debating whether I want Mexican or Thai or Indian that day,” he says. “It’s boring, but it works.” 

Putting this all-encompassing discipline in place helps unburden him from unnecessary cognitive load and lets him bring his fullest effort to making the decisions that really matter. As a CEO, the stakes for some decisions can be quite high, because their outcomes reverberate and impact the lives of tens, hundreds, or even thousands of people in the organization.

“You have to be ready to sacrifice,” he says. Structuring life to prevent potential distractions means that you can’t have a “normal life.” Sasha doesn’t have a television in the house, doesn’t use social media, lives close to the office, and spends less time with friends, family and on hobbies than he might otherwise be inclined to do.

In embracing this modus operandi, Sasha embodies the time-honored precept that discipline is not so much about resisting temptations (to waste time watching TV, in this case), than it is about removing them. 

So what motivates all this sacrifice? How does he know it’s worth it? 

Sasha’s mindset here is as fervently-held as it is clear: he believes that at the end of the year, the quarter, or even the day, you’re not going to reflect on what you had for lunch, or what you watched on TV, but on the things that you accomplished. 

This clarity and conviction — namely that  accomplishment is what ultimately defines one’s life —  is what makes the types of sacrifice and discipline demanded by the role of a CEO possible.

Time management during working hours

Every day when Sasha arrives at the office, he asks himself the following critical question: 

“What are the top three things I need to accomplish today?” 

He writes the answers down in a Google Task so they are always visible in his email tab. Over the years he has learned that if he tries to do more than three things in a given day, he gets distracted and ends up accomplishing less rather than more. Any fewer, and he feels he’s not doing his job well. 

Sasha subscribes to the Pareto Principle, which states that 80% of outcomes are caused by 20% of inputs. It follows that a CEO should focus on identifying the most productive inputs and make them the priority when it comes to time and resource management. 

Creating his list of the top three priorities of the day helps Sasha ensure he is spending the majority of his time on things that have the chance to really move the needle, instead of chasing a potentially infinite task-list of things that may be of marginal importance. 

A CEO’s time is best spent prioritizing and allocating resources like time and people at the company-wide level. Accordingly, Sasha habitually asks himself: 

• What do we want to accomplish this week, month, quarter? 
• How are we doing against the plan? 
• What are the potential risks that would derail us? 

He sees it as his job as CEO to allocate resources and prioritize work on what has the biggest chance to increase the value of the company. 

For any CEO, delegation is critical in managing resources effectively. That being said, there are some functions that only a CEO has the unique purview and context to own. Changing priorities, for example, or shifting resources, spending money on something outside the budget, or deciding to work on a feature that’s not on the roadmap. 

According to Sasha, a critical skill for a CEO is to know when to say “this was the initial goal, but it’s no longer the best use of everyone’s time.” 

It’s also the CEO’s job to put in place safeguards to ensure that the company’s initial goals are kept top of mind at all times, and each stakeholder is held accountable for their performance towards these key goals. 

The power of forcing functions

In the spirit of time management and accountability, Sasha believes in building external forcing functions into his routine both at a personal and a company-wide level. 

For an example of the latter, there’s a standing routine on Mondays at Puzzle.io for setting the weekly agenda. As part of this, every team lead documents their weekly priorities and commits to completing them. 

Then, on Thursdays, each team has check-ins to make sure they are on track to complete their projects. Finally, on Fridays, teams demo what was built that week. This structure ensures that there are multiple times a week where teammates are checking in with themselves on their progress and goals, and held publicly accountable for the commitments they’ve made and their results. 

To aid this fast-paced cycle, they try to hold only necessary meetings in a limited window, and Wednesdays are no-meeting days where employees can focus deeply on their work. 

“At every stage of a company, you should have forcing functions  — whether these be team meetings, monthly or quarterly reviews, board meetings, or artificial deadlines.” 

Sasha thinks of building a company as a game, with lots of smaller tasks that eventually lead up to a medium-sized milestone and eventually the next level. Each time you graduate a level, things get a little more complicated. Winning the game, like going public, is the ultimate boss battle for a company like Puzzle. 

By applying discipline to each week both at work and at home, by building forcing functions around these smaller tasks and milestones, Sasha can make sure his team is held on track to continue leveling up, and minimize the risk of derailment. 

But pre-set schedules don’t always work out, and issues arise. Not all levels can be beat on the first runthrough, especially if a CEO is new to the game. And over his two decades of experience, Sasha has grown familiar with both the mistakes people make early on in their careers as CEOs, and how to best safeguard against general interruptions or distractions as they arise. 

How to stay on track

1. Invest in People

As a third-time founder, Sasha has learned how integral it is to surround himself with the right people.  

At his first company, he took a more intuitive approach towards hiring, looking for people with high general intelligence and plenty of potential to grow. As his commitments as CEO grew, however, he quickly learned that he couldn’t maintain this hands-on approach to employee mentorship and development.

Related is the question of how best to spend time developing talent: given the scarcity of a CEO’s time, do you invest what time you have in your 25% highest performers, your 25% lowest performers, or the 50% of your employees who are somewhere in the middle? 

As his professional career has progressed, Sasha has had to shift his mindset towards prioritizing his high performers “You can build people up to a certain point, but after that it may not be the best use of a CEO’s time,” Sasha says. “People need to take responsibility for how they grow with the company.”

He believes in developing relationships with his employees and making sure they have the mentorship and resources they need to contribute to their maximum potential, but also that CEOs need to be able to delegate effectively in order to make sure their time is being used to achieve the greatest impact, which means that he doesn’t have endless time to carry employees who can’t scale themselves. 

“Your job as CEO is to build value for your franchise. Ask yourself: is this person creating value or holding the organization back from it’s potential?”

Hiring just ok employees can also lead to more personnel issues down the line, as these employees go onto hire their own teams. “As the saying goes, A players hire B players and B players hire C players. As A players don’t want to work with B or C players, eventually you are left with C and D players.” 

To protect his time more effectively now that he’s working on his third company, he is prioritizing hiring more senior talent who already have the relevant experience needed to get work done on their first day on the job. 

This is because investing in experienced talent allows a CEO to delegate work more easily with confidence the job will not just get done, but get done above expectations.. 

By maintaining the seniority and strength of his team, Sasha can better protect his time, make sure his goals stay on track, keep the talent level throughout the company high, and trust that department goals that contribute to overall company success are in good hands. 

2. Keep it Simple

Sasha reflects on how many more productivity and time-management tools there are now than there were when he started his first company. “There are so many cloud services... and there’s feature overload.”

Less is more with productivity tools, he says. Sasha favors using simple, straightforward tools like Google Tasks, Linear, and Notion, which are less likely to lead to distraction.

These tools embody the discipline and accountability that are at the heart of his leadership style. 

Google Tasks, for example, sits neatly in his Gmail inbox, and makes it as simple as can be to add and complete tasks: no tab switching or desktop app needed. 

Linear allows him to clearly see what everyone on his team is working on, and makes it easy for him to reprioritize as needed. 

He doesn’t check in too often, though. “It’s taxing to keep all these different statuses in my head, so if a predetermined date passes and I have not explicitly heard from my team, I have to trust that it got done.”

This goes back to hiring the right people, who can be relied on to stick to deadlines. 

“Things come up. Life changes. Market changes. Product changes. That’s all fine. I just need communication and trust so we’re all on the same page.” 

By using tools like Linear that foster team-wide transparency, he can encourage that communication and trust while also applying forcing functions to help everyone stay on task. 

Straightforward, simple, fast productivity tools help maintain structure while also minimizing distractions by virtue of their simplicity. 

3. Understand Yourself and Your Company

According to Sasha, another mistake that first-time CEOs make is not taking the time to fully think through and understand the value of their company. It’s their job to break through the noise and see the bigger picture so they can prioritize and allocate resources accordingly. 

When the nature of a company’s value is not accurately captured by its CEO, they cannot do this optimally. Money ends up being spent on the wrong things, and the company may gain momentum in the wrong direction. 

“When an early-stage investor gives you $1, they want $100 of their money back. How are you going to do that?” Sasha says. “When you don’t think about this question all the time, you end up spending money on unintentional stuff. Every spending decision should directly contribute to your company’s value.”

Another mistake first-time CEOs make is focusing too much on product, and not enough on distribution. There are tons of amazing products that may never see the light of day because a CEO doesn’t pursue distribution effectively, and money runs out early. 

It’s not simple to make the mental switch from founder to CEO. “You have to move from ‘I have an idea’,” Sasha says, “To being accountable to shareholders who expect you to provide them a return on their capital, to hundreds of people who rely on you for their livelihoods.” 

You have to know yourself, and be ready for the lifestyle. Sasha implores founders to ask themselves: If this business is successful, what does that truly look like? Growth is motivating and energizing and exhausting. Do you have the skills you need? And if not, what people do you need around you to help you through it? 

Get to know what works for you

Sasha attributes his track record of success at highly profitable companies to his emphasis on discipline, and forcing functions that create accountability for both an individual and an organization. 

He also acknowledges that every CEO is different. There are various species of CEO - venture-backed, angel-backed, bootstrapped, and others — and no prescriptive manual on how each should spend their time. 

The important thing, he says, is to “do what you need to do to keep performing.” Hire the right people, understand your product’s value, and then find the things that keep you accountable and on task and build value every day; find a schedule that works for you and stick to it.