A founder’s life leaves little time for pause. From the moment that the next big startup idea strikes, the tempo is set by the breakneck quest to scale. There’s always another hole to patch, another fundraise, another urgent priority that compels founders to be both masters of time management and of managing stress in a pressure-cooker environment. Pulling the brakes on the forward-barrelling train of startup life seems unthinkable — and if you do dare to halt the momentum, it can feel like pitching into a free-fall.
Earlier this year, Sasha Orloff took the plunge. In January 2019, Orloff published a short post straightforwardly titled “My Next Steps.” In it, he announced that he was stepping down as CEO of LendUp, the company that he co-founded and scaled over seven years. He noted that he didn’t have another position lined up; rather, he planned to take time off (100 days, to be exact) to reset, reflect and reassess where he wanted to go next. During his period of reflection, he also committed to an ambitious endeavor: to have 100 coffee chats with other founders, CEOs and investors as he sought to gain wisdom on career transitions.
Orloff’s hundred-coffee hiatus lends a view into the lesser-told story of founder life: the story after the startup. “In the frenzy of startup life, founders are just trying to keep up with the next pressing demand,” says Orloff. “But when your startup has grown into a fully-fledged company and you’re ready to leave it, you confront a new, almost existential challenge: deciding what to do next.”
A number of paths open up to founders. Do you stay on and learn the ropes of managing a larger enterprise? Do you launch into the frenzy again as a serial entrepreneur? Or do you try on a new role altogether?
From how to think through your own personal and professional development, to navigating uncertainty during inevitable periods of transition, the learnings from Orloff’s journey are valuable to founders at any stage, whether you’re stepping down after a successful acquisition, fresh off a failure or in need of a sabbatical for some self-care. Even if you aren’t a founder, we think you’ll find valuable advice on contemplating career transitions, structuring time off and plotting next steps.
In this exclusive interview, published 203 days after the start of Orloff’s sabbatical from startup life, he’s opening up about the insights he’s gained from his chapter in transition. First, he discusses the factors that led up to his decision to step down, providing useful frameworks for other founding CEOs to think through the dual nature of their roles. From his 100 coffee chats, he shares his networking tactics and the wisdom he gained from sage operators across tech. Finally, he offers founders a way to think about cultivating their growth and goals after deciding to move on. Orloff’s lessons serve as a reminder for entrepreneurs to take a pause if they need to — and to leap into the unknown with confidence.
There are certain elements of the startup success story that we’ve come to know by heart. The tale begins with a founder’s humble beginnings, follows the trials along their hero’s journey, and finally ends with a glorious exit, our protagonist still at the helm as founding CEO.
To an observer, it would seem that Orloff was living the startup fairytale. As the founding CEO at LendUp, he had carefully scaled a company, growing it from two co-founders to 250 employees across two offices and raising a $50M Series C. He had done everything he was “supposed” to do. Even so, he couldn’t shake the feeling that something was out of balance.
When he first felt the shadows of uncertainty, he dismissed his own misgivings. “There’s so much pressure from the press, from your board, from your team that the founder should run the company from inception to multi-billion-dollar company,” says Orloff. In an industry that glamorizes mega-success and dramatizes founder failure, founders often feel like they’re expected to stay on as CEOs all the way to IPO.
Furthermore, the structure of venture capital funding has shifted over the past twenty years, Orloff observes. “When I came into Silicon Valley, it was generally accepted that the founder would transition out and institute a more seasoned CEO at some point. This has changed for a variety of reasons, including more availability of capital, lower cost to incubate ideas and investors' willingness to keep founders at the helm, which means founders often have the opportunity to stay on for longer. That’s great if that’s what you want as a founder, but you should also be cognizant that you’re not feeling pressured to stay position longer than you want to be,” he says.
The combination of media and venture funding seem to push the narrative that staying on as founding CEO is the only definition of startup success. “While we should certainly celebrate people’s achievements, the Bezos and Benioff figures of the world get the lion’s share of the spotlight. But for every one of them, there’s also Reid Hoffman or a Larry Page and Sergey Brin, who handed the reins over to someone else when it was time to move on. In reality, people who become and remain founding CEO are rare. Don’t feel like you have to push yourself into a template of success.”
As he addressed the doubts that gnawed at him, the problem became clear: “My company had finally reached the point where what it needed and what I was good at and interested in doing had become very different things,” he says.
Up until this point, Orloff had never second-guessed his role as founding CEO, because he never had to. “In the beginning, the responsibilities were one and the same. But years down the line, the ‘founder’ and ‘CEO’ roles became more and more divergent,” he says. “What I enjoyed doing as a founder was turning a proof to a concept, finding product/market fit and scaling. Now that my company had reached this point of maturation, I was being asked to do something completely different: LendUp’s a fintech company, so as we grew, we were confronting more regulatory considerations, more complicated problems that called for a different kind of expertise than what I had honed as a founder. Even though my passion for the company hadn’t changed at all, I wasn’t sure that was the work I wanted to take on anymore.”
A founder creates something from nothing. A CEO manages something that already exists. They’re two totally different jobs, drawing from completely different skills. Not everyone is suited to juggle both roles.
Here, Orloff sums up the two main axes of difference between founder and CEO — and explains why “founding CEO” might not be the right role for everyone.
Responsibility: “As a founder, you’re motivated entirely by trying to solve a problem and find product/market fit. You have the most control over the company,” he says. “When you’re a CEO of a seven-year-old, 250-person company, you’re spending more time thinking about capital allocation and company resources. Your primary responsibility is fiduciary to the shareholders. You might be managing an increasingly active board. It calls for a completely different skill set from the entrepreneurial tools you honed in the first few years of the company’s lifetime.”
Risk: “Founders, by nature, have a big risk appetite. You have to be able to feel comfortable, even exhilarated, placing big bets on an idea that might not even pan out. On the other hand, if you’re a CEO of a company that’s already reached a level of success, you can’t take such bold gambles anymore. You need to exercise more care, because you do have something to lose.”
“People and companies scale at different rates,” says Orloff. “At some point, in the company’s growth, the innovative, risk-taking qualities of a ‘founder’ becomes less useful, while the professional, careful qualities of a CEO become more important. If you find that what you enjoy and what your company needs diverge, that’s actually okay. In my case of leading a company in a well-defined industry like financial services, someone with greater breadth of experience than I had would bring a lot more value to the shareholders as the company matured.”
The role of “founder” isn’t static. Your responsibilities in Year 7 are going to look fundamentally different from what they looked like on Day 1.
That said, if founders start feeling discrepancies between their work as founders and their new responsibilities as CEO, there are ways to make up the difference. “For founders who want to remain a CEO, I’d strongly advise getting a career coach,” says Orloff. “In the beginning, I didn’t realize how many people had one. At around the time we were starting to scale, I attended a Y Combinator session with 24 other growth stage founders. Ali Rowghani, who was leading the session, said, ‘Raise your hand if you have a coach,’ Everyone raised their hand except me. I thought to myself, ‘Okay, I must have missed that day of founder class.’ And I started interviewing coaches the next week.”
Coaches can help you work on those skills that are paramount in larger companies. “One CEO skill I had to learn, that I didn’t necessarily have as a founder, was how to manage career executives,” he says. “When you’re a startup, your leadership team can look like a ragtag gang of highly talented misfits, who, like you, are improvising as they go. But once you scale and attract established talent, the makeup of your leadership team changes. Managing a C-Level executive with 20 years of experience is a totally different ballgame. I relied heavily on my coach and annual 360s to help me grow that skill.”
CEO, founder, or both? A career litmus test for founders.
Even though coaches help founders feel better equipped to tackle the dual roles of founder and CEO, founders still need to actively assess their own feelings about the job. “As the company is scaling, check in with yourself at the various inflection points in the founding CEO’s career. How are you feeling as the CEO role starts to form around governance? As you start to offload responsibility and delegate? Are you still excited to do that work?”
For Orloff, he started reflecting on his role as the company preparing for its Series D. Below, he the inflection points where founding CEOs should take their emotional temperature to help make a decision about whether it’s time to move on:
When you start managing managers.
When the company forms a board, typically after series A.
When you’re no longer in control of the board.
When you’re cash flow positive.
When you’re actively planning the IPO.
“If at one of these milestones you realize that you’re no longer happy, that this work is no longer personally meaningful for you, it’s time to start having these conversations with the board,” says Orloff.
If you’re excited to build managerial skills, then by all means, stay on as founding CEO. But if you’re constantly frustrated and unhappy, it’s better for your customers, your shareholders and yourself to bring on someone who is excited about the job.
Manage transitions with casual compassion
Orloff admits that the opportunity for him to take his leave came sooner than he anticipated: LendUp split into two companies, focusing on its lending business while spinning out Mission Lane to run its credit card operations. The strategic change offered Orloff a rare window of opportunity to make his leap.
“Whether you’re stepping down or marking another change in your company’s direction, take care with your messaging. There should be almost an excess of intentionality around transitions,” says Orloff. “Any kind of transition is bound to make people uneasy, because change is frightening. With a founder stepping down, employees and investors reasonably wonder if there’s some uncomfortable dynamic or ominous future behind the curtain.”
The stakes are heightened for a founder-led startup. “Unlike a massive enterprise, where professional CEOs come and go, a founder CEO’s transition carries far more emotional weight. On top of that, once news gets out, the story can take on a life of its own on Twitter and beyond. Your internal communication strategy is your opportunity to take control of the narrative, right from the beginning.”
He shares his step-by-step guide for messaging a transition:
Take time to plan your rollout. “The longer you plan in advance, the smoother the transition will be, and the higher your likelihood of finding the best replacement. I discussed it with my cofounder first, then planned the messaging privately with the board and the head of comms six weeks in advance. We iterated on how to share the news, to strike the right tone and give enough context.”
Give opportunities to reflect and react. “We were definitely intentional about timing the announcement to leave people plenty of space to process and ask questions. I didn’t want to say Enjoy Friday afternoon everybody, and by the way, I’m stepping down as CEO! That would be a terrible; you don’t want to put your employees in that position. So, we made the announcement on a Wednesday, and I devoted time for a Q&A. On Thursday, we did a lunchtime Q&A, and I answered questions that people had anonymously sent in. On Friday, we had an all-hands happy hour, where I said good-bye and answered lingering questions.”
Be a human about it. “I had initially drafted an email to send to the entire company, but I ended up reading it at an all-hands. Or at least trying to. I think I made it a few sentences before I started to get choked up and tears started flying — and I almost never show emotion. Someone had reminded me, ‘This isn’t a time to be stoic.’ When you’re transitioning, it’s okay to show your emotions and be vulnerable. It’s okay to be sad and excited for the future. During that Friday happy hour, I made sure I was wearing my LendUp shirt, to signal that I would be involved as a board member and still cared a lot about the company.”
On the first day of his hiatus, Orloff looked at his calendar and saw… nothing. His schedule, which had been virtually booked solid since he founded LendUp, was a blank canvas. “The gravity of the situation was just hitting me, that I just left these years of intense, lock-step scheduling without another logical next step. You don’t just Google ‘What should I do after leaving the company I built?’ I felt confused and disoriented. It was honestly intense.”
So much of a founder’s identity is wrapped up in their company. When you pour your life into building something, and then you change course, you almost have to redefine yourself. That intensity of introspection can be daunting.
But in spite of the initial confusion, the pause was also an opportunity for Orloff to regain clarity. “Scaling a startup leaves so little free time. When I was CEO, I was evaluating whether every 15-minute increment was the most valuable use of my time. At worst, it can get to the point where you feel guilty for spending time on anything outside of work, like relationships or your own health. Taking a break is a chance to reclaim a sense of who you are and what you value, outside of your company.”
Whether you’re a founder preparing for a big transition, or looking to take a brief intermission, Orloff offers some pointers on giving shape and color to the white space.
First, disconnect fully. “Taking time and distance away from your work helps you see opportunities that are outside of your immediate world, and it puts your own experience into perspective. I started my transition with a 14-day email and phone detox, but you don’t have to take a hundred-day break to do this: Scale the detox period down to fit your personal runway, whether that’s a weekend, or an afternoon of reflection.”
Give yourself a framework for free time. “For professional and personal transitions, I highly recommend William Bridges’ book Transitions: Making Sense of Life’s Changes. The book doesn’t claim to solve or speed up your transition, but it focuses on learning to understand the circumstances that led up to it and opening up a pathway to think through what might come next. I also found that creating structure around a break period was key — quite a few people told me that their sabbatical time flew by, and they didn’t accomplish as much as they hoped. Having a structure, on the other hand, helped me be far more intentional about my time. Otherwise, you’ll find out, as I did, that it’s very easy to turn on Netflix in the morning and too many hours later suddenly realize that it’s dark outside.”
Tend to your health and relationships. “I can’t underscore enough the importance of taking care of yourself, whether that’s planning for physical exercise or working on your mental health. Meditation apps like Waking Up makes it easier for full-time founders to incorporate mindful moments throughout the day. I also made sure to prioritize fun. For me, that meant spending time with friends, traveling, and planning activities with my family, like family dinners and ‘science Saturdays’ with my kids.”
Rediscover your beginner’s mind. “I decided to make two broad learning goals, professional and personal. For my professional goal, I reflected on areas where I wish I was stronger as a CEO, and then enrolled in classes on corporate finance, board governance and talent analytics (I highly recommend this course from Harvard). For my personal goal, I started taking tennis lessons. That one is definitely still a work in progress.”
For 100 days, Orloff committed to recharging and reactivating his rookie mindset. But by the hundredth day, he was ready to start exploring something new more seriously, which meant activating his network to mine for opportunities.
Fortunately, he had a pile of inbound leads as people had been responding to his LinkedIn post announcing his departure. “If you share with your network that you’re moving on, folks might naturally reach out to ask after you, or to offer their help. So when people asked to meet up, I just started saying yes to everything.”
Orloff’s generosity with “yes” opened up even more opportunities: You should talk to this person, or Let me connect you to… which spurred the idea of tallying up 100 coffee chats. Over the next hundred-or-so days, Orloff took meetings with founders, CEOs, entrepreneurs, investors, coaches, executives and other business leaders.
Eventually, he focused on prioritizing meetings that could help him think about his next steps. “I wanted to ask people how they managed transitions from one job to the next,” says Orloff. “I also wanted to focus on talking to people who would help me find inspiration about new ideas and new problems to tackle.”
Here’s how Orloff strategically narrowed his contacts list:
Inbound contacts: “Some people reached out after I announced my stepping down on LinkedIn. That ranged from colleagues who wanted to catch up and reflect on our time at LendUp, to friends.”
Operators who had been in his shoes: “Here’s where I got more tactical: I focused on people who had been in my situation and would be able to give me guidance on how they navigated their own transitions. I reached out to CEOs I was at least loosely connected with. I prioritized people who had left the company they had founded, or had taken over as CEO after the original founder.”
Investors: “While I viewed my own career transition at close range, VCs have a unique perspective. They have an aerial view on these situations, and they’ve seen and analyzed plenty of them, too. I thought they’d lend a helpful perspective on the market and opportunities and what that might mean. So, I started with my own investors in LendUp. I also wanted to ask them how they thought about the market and what new opportunities there might be.”
It’s worth noting that coffee chats might have been a misnomer for Orloff. “I’m actually not a coffee drinker,” he laughs. “I’d usually stack five or six chats in a day, too, so actual coffee chats might have been dangerous. We could call this project ‘100 decaf mochas and some herbal teas,’ but I’m not sure that’s got the same ring to it.”
From VCs to veteran founders, each persona that Orloff reached out to had common words of wisdom to share for founders in transition. Orloff reveals them here:
New ex-founding CEO? Welcome to the club.
Meeting with people who had gone through a similar crucible and come out the other side intact reassured Orloff in his decision. “People reassured me that handing over the reins to another CEO was not only a smart decision, but an overwhelmingly common one. It took a lot of people saying that to me before I could internalize that, but I’m glad they did. Embracing vulnerability by opening up to other people is illuminating, because you realize that your doomsday concerns aren’t actually even special,” he says.
“One interesting thing they pointed out was that by moving on, I was generating new opportunities for others and myself,” he says. “By founding LendUp, scaling an awesome company through its early stages, and then stepping down from it, I was creating space for a professional CEO to take their own dream opportunity, create as much value in that role as possible and make the company better because of it. And I, in turn, had this opportunity to do something exciting to me.”
Fear of the sophomore slump is real — but so is the possibility for growth.
Speaking of new projects and new beginnings, another prominent trend in Orloff’s conversations was a fear that founders particularly fall prey to: that their next project will never equate their previous success.
“Fear of the ‘sophomore slump’ was acute among founders who left and started another company. And I admit that, no matter how many times people tell me not to pay attention to those irrational fears and insecurities, I feel it too. For my next venture, I obviously want to create something that’s bigger and has a larger impact than my first — and that’s intimidating to say out loud,” says Orloff.
But both founders and VCs pointed out that seasoned founders start their second acts from a position of strength. “It’s a beautiful and exciting thing when you start your first company and discover your own potential. By the time you’re searching for your next opportunity, you’ll already have built the skills and disposition you need to do it again. Only this time, you’ve got a few more connections, and a lot more know-how. In spite of those voices in your head telling you that you can’t replicate success, in reality, you are objectively more likely to be even more successful.”
Reframe your anxiety into motivating energy. If you’re going to start another company, you need to go big with your ideas, and you can’t go big unless you let go of apprehension and embrace audacity.
Throughout his period of reflection and conversation, one question weighed on Orloff: How long is “long enough”?
“I didn’t want to come back too soon, at the risk of burning out again,” he says. “Then again, people often jump back in sooner than they want because of the fear of losing their network, fear of missing out on other opportunities, or the feeling that they had something to prove after their last job.”
He tried to ask others who had taken sabbaticals how they approached this decision. “I kept asking them, ‘How do you know when to come back?’ Everyone said, ‘You just know,’ which was the most frustrating answer,” he says.
After about six months on hiatus, Orloff did, in fact, “just know.” (As it happened, most other former founders told him that they themselves had also taken six-month breaks.)
“I felt very privileged to be able to take that much time off between gigs and have a family that supported me throughout the journey. You have to make the decision that’s best for you and your family’s financial health,” says Orloff. But if you are lucky enough to have the runway to spare, he suggests a quick personal diagnosis to figure out when to end the sabbatical and re-enter the industry: “When you’re thinking of coming back to something after a transition, ask yourself how you feel when you think about future opportunities. Are you excited, or still exhausted? If you’re waking up feeling excited to tackle something new, that’s a good indicator you’re ready to dive back into the fray.”
Reenergized, Orloff found himself facing another blank canvas: not just a newly-freed calendar, but the opportunity to determine the design of his career. “Even if you haven’t taken a formal break, throughout the course of your career you will inevitably come upon a crossroads where you get to decide what to do next. It can be useful to have a framework to think through the (hopefully many!) opportunities that are before you,” says Orloff.
He offers four frameworks he used to help hone in on opportunities and make decisions for the next chapter.
Five pathways after the first startup
“Make a list of the pathways that sound potentially exciting to you. Evaluate each of them deeply. Can you start to cross them off, one by one?” says Orloff.
Orloff’s hundred coffee chat interviews were useful in uncovering the diverse pathways that founders often forge after moving on from their first startup:
Join the ranks of repeat founders. “When you’re a founder, you’ve proven that you’re capable of creating something, and that’s really exciting. Becoming a serial entrepreneur is a way to keep creating. That said, not many people have that comfort level anymore — you have to be able to have no income for a while, network to put together a founding team and attract talent, essentially starting from scratch all over again.”
Sit on the other side of the pitch presentation. “Being an investor could be an exciting way to apply your founder experience to supporting other founders. But the way I saw the role, you’d also have to commit 10 years to investing before you figure out if you’re any good at company-picking. At this stage in my life, I wasn’t ready to make that commitment.”
Coach up-and-comers as an expert-in-residence. “Instead of going all-in on becoming a VC, you might apply your hard-earned knowledge and insights to help a VC incubate ideas. As an EIR, you can help others with their ideas, without the expectation of being a permanent member of the team. At the same time, you can go to an investment committee, get an aerial view of all of these different companies, and study the market until you feel inspired to embark on your next business idea.”
Work at a large company. “The pro of working at an Uber or an Airbnb is obviously a great, stable salary, and working on interesting, large-scale projects. The question you have to ask yourself is: Am I solving the problems that I really want to be solving? Or, am I all right with solving the problems that, while important, other people perhaps are more passionate about?”
Jump aboard a fast-growing startup as number two. “Another path founders might consider is joining as the number two at a fast-growing startup. You still have the tools and experiences from scaling your early-stage company that you’d be able to apply as COO or president of a fast-growing startup. The challenge here is shifting from the number-one to the number-two mindset. So you have to ask yourself: Can you learn how to see the startup outside of your identity? When you’re a founder, your startup is your baby — can you go from being the parent to being the babysitter? You have the opportunity to be a more objective, less emotionally-attached leader, which I personally think would be an exciting, new set of muscles to flex.”
Evaluating a new business idea
For founders who have another entrepreneurial itch to scratch, Orloff suggests finding direction by asking yourself a simple series of questions:
Where are the big problem areas in the world?
What personal skills, advantages or insights do you have to be able to help solve it?
How can you turn this into a viable business idea?
Orloff gives an example of how he thought through this framework: “While I was at LendUp, one issues that I found myself wanting to learn more about was the relationship between technology and working-class Americans. I increasingly became aware of an entire market outside of major urban areas, who were appreciative of technology but didn’t necessarily have the tech industry focused on building for them,” says Orloff.
“During my time off, I was exploring how I could apply my background in entrepreneurship, technology, and experience with working-class Americans to democratize access and improve their lives,” he says. “I’m not sure if that’s exactly what I’m tackling next, of course, but it’s something that I’ve been mulling on for months. If you’ve been thinking about a business idea for a long time, and repeatedly, it’s a good sign that you are passionate about it and should at least explore moving forward with in some capacity.”
Frameworks for broader ideation and imagination
Finally, for more macro-level career brainstorming, it can be useful to have frameworks that allow for a breadth of possibilities. Orloff shares two methods he used.
“One of my coffee contacts introduced me to ikigai, a Japanese concept for zeroing in on what gives you a sense of personal and professional fulfillment,” says Orloff. “Essentially, your ikigai, your role that gives you purpose and excitement, lies at the center of four priority areas.”
“What I valued about this model was that it blended the theoretical with the personal and actually acknowledged compensation,” says Orloff. “However while I love the concept, I found it challenging to apply this framework to reality, because it was so open-ended.”
He ended up needing a specific methodology to define his path. “Most of the people I spoke with suggested that I make three lists, under three major buckets,” he says.
Skills you want to build
Industries you want to work in or experiences you want to have
“Once you’ve listed this out, you should be able to articulate what you want in one sentence: Once you can tell people, ‘I’m interested in exploring role X in industry Y, and my must-haves are Z,’ then it will make it much easier for your network to help you get to the place you want to go,” says Orloff.
“At first, I was afraid of defining what I wanted out of my next career move too narrowly or too soon,” he says. “But as it turned out, going with a more specific route helped me find more opportunities that were aligned with what I wanted. It was far more helpful than the broad stroke I was trying to employ before. People want to help, but they can only help so much if you yourself don’t know where you’re headed. With a more specific objective, you can much more effectively maximize your network.”
For founders, life beyond the first startup can be daunting. “To be honest, when you’re in the moment, it doesn’t seem like there is a life after the first startup,” he says. “You’re just so intently and intensely focused on this one company for so long, it’s hard to think of any other way to be.”
After spending years scaling his company, Orloff had the opportunity to step away from the churn and ceaseless intensity of the company-building world. His 100 coffee chats with 100 seasoned operators unearthed wisdom both for founders in the weeds of scaling an early-stage startups, as well as founders who are also contemplating their own transitions.
Orloff reminds founders that people and companies scale at different rates. At a certain stage of company maturity, founders and CEOs will have fundamentally different roles. Orloff advises all founders to hire a coach and start developing their CEO skills sooner. That said, it’s a sign of strength and self-awareness to admit when a role has evolved past what you’re interested in. If you need to step away from startup life, be purposeful with your break — and in spite of the fear and uncertainty, know that there’s always a path forward.
Founders: You are not your startup. It can be hard to believe, but there was a life before it, and you will continue to lead a rich and fulfilling life afterward, no matter what kind of adventure you step into next.
Photography by Bonnie Rae Mills.