It’s been exactly one year since David published the first episode of the Not Another CEO Podcast, and six months since we came together around a joint mission to bend the curve for founders/ceos.
Since then, Not Another CEO has grown in ways we could not have imagined. Only 3 months after launching this publication, there are now more than 10,000 subscribers; over 50 founders/ceos have contributed their stories and perspectives; we have hosted events attended by hundreds of startup founders, ceos and top tier operators. We have served hundreds of CEOs through deep conversations in our advisory work and founder/ceo one-on-ones. We have exchanged thousands of messages with Not Another CEO community members.
We have learned a ton. We have reflected on, and thought about, how the wisdom of this collective group of founders/ceos triangulates with our individual experiences running businesses. Through it all, we have sharpened what we believe bending the curve for CEOs actually means. A year in, here is what we believe:
There are 7 core pillars of running any company. These are the foundational elements that, when aligned, create the engine of a great company. These are 7 pillars that every CEO, no matter their stage or sector or product, must learn to navigate.
We are all human: people over-index in some areas naturally, and as a result of their work experiences. Every founder/CEO is constantly growing. (Us included).
Bending your curve as a Founder/CEO means thinking critically about the state of your company, and which pillars you, your team, and your business are strong versus weak in. It means being brutally honest & self-aware, and taking the necessary actions to evolve and grow.
We hope this piece will help jump start your understanding of the 7 pillars (or serve as a reminder of them), prompt you to begin an unwavering inventory of where you and your business are strong vs weak, and begin charting the next set of actions necessary to evolve.
While the details will look different from company to company, such as your team, market, stage, and tools, we believe the 7 pillars apply to everyone. Whether you’re leading an early-stage or late-stage company; a hardware or software business; are embracing AI; are b2b versus b2c; or are bootstrapped as opposed to VC backed, the pillars are universal elements you must master.
They do not operate in isolation; each touches the other. They are the things that truly matter: the rest is a sideshow. Here are the seven pillars of being a CEO.
1. Beginnings and endings
As contributor and community member Anthony Corletti put it: “all founders start and all founders finish.”
The beginning of a company is critical. From who you start your company with, to its legal structure, how you split equity, decide on a name, and more, these decisions matter (a lot). Nadia Boujarwah, former CEO of Dia&Co, shared: “For me and my journey, my cofounder relationship was probably the most important [decision I made].”
First time founders often rush through these decisions, impatient to start building. People building their second or third business almost always take more time to get this part right. They will shape a lot down the line, including how the company ends, even if that’s decades later.
To bend your curve when starting out, you should be intentional when answering questions such as:
What type of business entity should we form?
How will we fund this?
Do I need cofounders? How do we split equity fairly?
What name should we use?
Are we offering equity to employees?
Are we a remote company? Hybrid? In-office?
How do these decisions affect and support our business strategy (product, distribution, growth, monetization, etc)?
Fast forward to the end of a company's life, and there are a whole other set of existential issues. Bend your curve by being aware that decisions you make years earlier, going all the way back to the start, are most often the core drivers of how you end. End of life issues include:
Will we be able to sell this company?
How do we avoid failure, or do we need to shut the company down?
Who is the right acquirer for this business? How do we position ourselves as an asset to them?
What is the right time to exit? (it is not always the first acquisition offer)
What is the most tax-efficient way to structure a deal?
When shutting down, what do we need to do, and how do we best position ourselves to build again?
Exiting a business is not straightforward; lightning does not just strike. A meaningful exit often involves years of strategic business development led by the CEO. As Alan Masarek, Former CEO of Avaya, who made dozens of acquisitions told us:
Almost never did the call [on an acquisition we made] come in from the investment banker ‘you should look at the book of this acquisition I want to send you.’ The acquisitions [we did] came about from the team…based on fulfillment of a well articulated strategy…at Vonage, the acquisition of NextMo in 2016 was the complete gamechanger of the company’s trajectory…that came about because one of my team members who I respected a great deal started talking about it.
Bending your curve also means recognizing that how and when you exit is a deeply personal decision. Check out this story from Jindou Lee, Founder and CEO of HappyCo, on why he rejected an early acquisition offer:
Transitions in, and transitions out of your business deeply matter. The early ones set your direction, and the later ones define your legacy. Great Founders and CEOs know how to properly begin, evolve, adapt, and end gracefully.
2. Hiring, firing, and inspiring
No CEO succeeds alone. The success and failure of a company comes down to its people.
Many first time founders/CEOs hate and make little time for “HR” or “people management.” The best CEOs know that building and leading the right team for your business is one of the most important (and challenging) parts of the job. It involves building a high functioning team by inspiring people and shaping culture, managing performance, and helping people grow. And yes it involves firing people.
To bend your curve when hiring, firing and inspiring, you should:
Define company values that guide day to day decisions
Hire employees based on those values, the best fit for your business, and the unique stage that your company is at
Train team members across your business on how to conduct proper interviews, provide helpful 360 feedback to their peers (and managers), and coach others
Compensate people as appropriate for their role, seniority and impact, and align that compensation to business strategy and growth
Conduct employee performance reviews that influence compensation, team member advancement (and managing out)
Properly conduct layoffs and fire underperformers (yes, there are right and wrong ways)
For example: hiring looks very different in the early days compared to at scale. Craig Walker, CEO and Founder of Dialpad, shared this: “I’d say the biggest challenge is hiring the right people at the right time, and being able to recognize” who is a fit for the current stage you are at.
Early on, you want to hire generalists who can do a little bit of everything. Later, you’ll need specialists who raise the bar in their area of expertise. Knowing when you have hit this inflection point, and you need to shift what you hire (and manage) for is hard. Especially when you are a CEO living and breathing the business every day.
Similarly, creating company values that are authentic, memorable, celebrated and lived is perhaps the greatest driver of organizational health and performance we have found. John Fazzolari and Anthony Serina, Co-founders and Co-CEOs of Revivn, believe values are so important that every year they “re-onboard people…to go through the values again with them...this is a consistent thing that we’re constantly driving” to drive business results.
How you hire, fire and inspire your team is the glue that holds your team together and allows them to, as Alan Masarek puts it, “achieve often what they cannot even see yet, what they can’t imagine”:
3. Operating rhythm: your breathing apparatus
Your operating rhythm is the breathing apparatus of your company. It drives alignment, execution, and business outcomes. The best CEOs establish a clear format and observe a consistent cadence that aligns the company and keeps people focused.
Todd Olson, founder of Pendo, points to their operating rhythm as having a “dramatic impact on their success.” Pendo’s keeps him and his leadership team sane, and allows every member of their team to “at any given time…know our rallying cry for the year, what our top three priorities which ladder up to that…and understand how what they are doing, and how their individual priorities connect to the company’s top 3 initiatives and rallying cry for the business.”
But having the discipline to stay consistent and committed is the most common foil. So bending your curve in this area includes not just setting but most importantly sticking to a consistent cadence that starts at the board and executive level, and then touches every function and team member in your organization. Do you:
Regularly revisit your company vision and strategy?
Conduct a formal annual planning process, and quarterly financial re-forecasts?
Hold quarterly board meetings & investor 1:1s, and send written investor updates?
Host weekly executive leadership meetings?
Meet with your direct reports weekly/regularly to conduct 1:1s, and expect leaders/managers across the org to do the same?
Have (monthly) company-wide all-hands meetings, with organized agendas? Do you expect your functional leaders and team managers to do the same?
Track progress using mechanisms like OKRs and KPIs?
A consistent, dependable rhythm builds a culture of trust, communication and accountability at every level of the org, including for the CEO.
Dan Michaeli, Co-founder and CEO of Glia sees the CEO as “the pacemaker” of your operating rhythm, which brings multiple benefits. This includes “clarity, so reducing the ambiguity”, as well as “mobilizing the team…and sending the right message throughout the organization,” and finally “alignment” in “strategy and execution.” As he says, the “rhythm of the business, it creates important forcing functions throughout the year” and serves to “drive urgency throughout the business”:
And while driven by the CEO, your operating rhythm is not purely top-down. It’s also about giving everyone a voice, and allowing you to understand the pulse of the organization. This is particularly important as you scale. At Okedo, Dan Atkinson holds “AMAs every two weeks where someone can [ask] literally anything…anonymously and we'll answer..I think a lot of times people underestimate the power of the people in their organization, and the more you give them, the more they'll give back.”
4. Financing and investor relations
Every CEO has to answer the same fundamental question: how are we going to fund this thing? There’s no one right answer.
VC is not for everyone and every business. Your financing model should be a reflection of your business strategy, not the other way around. As Sean Griffey, CEO of Industry Dive, rightly put, many founders have “raised a lot of money and built businesses that should be doable [sustainable / with compelling founder economics], but because of their cap table, they're underwater the whole time, and the rest, you know, it's kind of a mess.”
There are many options: bootstrapping, seed-strapping, venture capital, private equity, debt. Each path has tradeoffs, and it’s up to you, the CEO, to decide the best route for your company. Bending your curve here starts with recognizing that financing, and managing investors, is an evergreen project; and admitting that there is nothing virtuous about raising capital, that instead it is merely a means to build, and part of the CEO toolkit.
This requires:
Choosing the right financing model for your goals, values, and business model
Building relationships with and recruiting investors who align with your vision
Knowing when to go to market and how much to raise
Being prepared for and running an effective fundraising process (crafting your investor story/pitch, creating investor urgency, managing diligence / dataroom dynamics, etc)
Managing board dynamics and running effective board meetings
Keeping communication strong with investors, and keeping them informed regularly
Leveraging investors as strategic partners, not just check-writers
Financing strategies change as your company grows, and its needs and business model evolves. Maybe you have bootstrapped, have never taken venture capital, but now are considering taking outside investment. That’s a tough call to make, and one that only you can make as CEO.
Financing is a direct reflection and driver of your core business, and the investors you surround yourself with will shape what you do operationally. As Kyle Porter, Founder and Former CEO of Salesloft, recognized: his investors pushed him into “believing the company can be bigger and better than I thought going in.” This will make you go faster, hire faster, and burn more. So financing will influence your goals around growth & profitability, and your exit strategy; it will shape who you hire (and when); how you build your product; how you sell; the customer you’re building for. It even impacts your culture.
And as Mike Lazerow, Co-Founder of Golf.com and Buddy Media, describes: VC backed companies are always raising, and building relationships often starts years before an investment is made. So you should “always return emails,” even when you are not actively in the market, no matter who at a fund reaches out. “Most of the time…you aren’t raising money, you are growing your network of potential investors by building genuine relationships. The best way to [do this] is to show you care for people regardless of whether they can give you anything in return.”
And because of all of this, when the much needed cash is in the door, your work is far from done. The best CEOs are in constant communication with their investors, meeting and sending messages with them regularly outside of board meetings. To parrot Ryan Westwood, CEO of Fullcast, “look at your cap table as a tool or a strategy to build the business.” Don’t be like the many founders we meet who “aren't in communication with investors. They're not…getting them as excited as customers and employees; they're not keeping up the relationship”:
5. Acquiring and creating raving customer fans
Attracting customers is the lifeblood of a startup. But attracting the right customers and turning them into raving fans is what you must do to grow efficiently and sustainably.
Your product isn’t for everyone. So, start by identifying your Ideal Customer Profile (ICP). As Tom Buiocchi, Former CEO of ServiceChannel, put it: “segment until it hurts.” Indeed, we have not spoken with a single Founder/CEO who feels their target customer is too narrowly defined; rather, problems proliferate when it is the opposite.
Most successful CEOs like Melanie Fellay of Spekit find themselves narrowing their customer focus over time. At first, Spekit spoke to any customer with a “problem around documentation and training, we're a solution, buy us”, but over time, they learned “the hard way..[that] you need to be a big enough company that you really have the pain of enablement” that Spekit solves. “Early on, we sold to customers that were too small…they don't really have someone that's going to be able to manage [our system] and be effective. And so [today] we really start at…like 100, 150 [employees], and we want to be the first” learning and enablement system used by the client.
Bending your curve begins here: with challenging yourself to narrow your ICP as much as possible, and a reminder that this is not a one-time exercise. Bending your curve finishes with being customer-obsessed. Every CEO needs to answer:
Who are we building for, and what is our ideal customer profile and buyer persona?
Are we building a sales-led engine, or is this a PLG motion?
What type of relationship do we want with our customers? Transactional, or high-touch?
How do we offer customers an amazing experience with our product, company and brand? How do we build enduring customer relationships?
How do we create meaningful thought leadership that resonates with our ICP and IBP, and attracts them?
How do we structure contracts? Monthly, annual, or multi-year?
What does our customer success motion look like (onboarding, QBRs, renewals)?
How do we build a community that aligns with our company values?
How does our customer engagement tie into, relate and drive product delivery?
How is customer obsession tied to our employee values?
Without a well-defined (and narrow) ICP, your growth will be unpredictable and unsustainable. You may never find product-market fit. But when you know who you are building for, everything else will flow: your product roadmap, customer acquisition and onboarding motions, pricing and contracts, and your customer support and success strategy.
We have also found that the best companies are customer-obsessed. This starts with your CEO and founders, and pervades every part of your company culture. As Diego Oppenheimer, Co-Founder and CEO of Algorithma, recalls: “You have to be customer obsessed…I don't see a world where this works, where…you don't have that obsession.” That obsession pervaded everything about Algorthima’s culture, including “free lunches on Wednesdays at the office. I had a little sign on the lunch table. It says, ‘remember who pays for lunch’...and it's the customers…we exist to serve our customers and provide whatever they need. That’s it.”
This obsession allows companies to build trust with and deliver value to their clients. Every touchpoint is critical in retaining, expanding, and turning customers into raving fans. Cofounder and former CEO of Marketo, Phil Fernandez, shared that their reputation of always having “the customers back…became so deeply entrenched” in their culture and go-to-market that going to “user meetings was like a revival meeting…customers just wanted to be there with us.”
When you know who you are building for, deeply understand and care for your customers, you can build your whole company and product around serving them. When your customers “just want to be there with” you, growth is a mere byproduct of deep trust and loyalty.
6. Shipping product
Your product is your promise to the customer. Bend your curve as CEO by owning the vision, setting the direction, and making the hard calls about what you build, why you build it, and how you build it.
This includes the existential questions such as: what problem are you solving, and for whom? How is it 10X better than the other options for my customer? How do I ensure the product is a painkiller, not a vitamin; a must have, not a nice-to-have? Answering these questions are acute early stage problems, but they require constant recalibration as your company grows, customers evolve, and the market shifts.
Key product decisions CEOs must guide:
Product vision: Are we building something transformative, or iterating on what’s already working?
Roadmap prioritization: Who decides what gets built? And how do we balance customer requests with long-term vision?
Pricing and packaging: How do we monetize what we’ve built? What does our pricing say about our positioning?
Build vs. buy: Do we develop everything in-house, or layer in third-party tools and acquisitions?
Customer feedback loops: Are we listening to what customers actually need or just what they’re asking for?
Team structure: How do our engineering and product teams collaborate? Do we have points-based systems, agile sprints, or something else?
Technical infrastructure: What are we building on (AWS, Google Cloud, OpenAI, Anthropic, etc)? Why? You need to make strategic infrastructure choices and not just choose the easiest option.
CEOs must set the direction, and be involved, but not all agree on how involved. Tom Buiocci shared that if his team was “debating a product feature…that did not result in a new offering that would generate at least a couple of million dollars? I stayed away.” But in contrast, Jeron Paul, CEO of Spiff, says, “I’m definitely personally passionate about what I give to my customers. So much so that I want to be involved in every aspect of what they receive…I like to be involved in every detail.”
Regardless of what level of involvement is right for you, we agree with Paul that most successful CEOs we see today are “starting to kind of migrate away from this dominant sales personality, to being [a] problem solver in chief.” Every product decision, such as roadmap prioritization and the tension between short and long-term bets, has downstream effects and sends a signal to customers. As CEO, you need to guide your team through these tough calls, whether it's the tradeoff between building to retain customers or attract new ones, optimizing for speed or scalability, or fixing bugs or shipping new features.
The best CEOs shape the conditions for great product decisions to happen consistently and for great customer experiences to be delivered. And when things need to change, Founders/CEOs should not restrain themselves when pivoting; as Mike Lazerow put it: be fast, and and be ruthless.
7. Your CEO support system
Only other CEOs know how lonely your job is, and the sacrifices that you have made.
You are expected to know and serve your customers best, set the vision for the business and product, create the rhythm, build and inspire your team, raise capital and manage investor expectations. You must inspire confidence and keep everyone moving forward even when things are most difficult.
Only you, as CEO, can do all of this. No one, not your executives, not your investors, not even your spouse truly understands what it means to walk in the Founder/CEO’s shoes.
And in order to make this all work, like every Founder/CEO before you, you will have to make many sacrifices in your life. As Kass Lazerow, Co-founder of Buddy Media recently wrote:
You can only do one thing at a time really well. If starting and growing a business is the one thing, other things (like your closest relationships) will suffer. And when other priorities are more important, the business will suffer. During these inevitable trade-offs, your friendships, family, and health inevitably get something less than your best.
If you aren’t willing to embrace and deal with these realities, that’s OK. But if that’s the case, we recommend you don’t become an entrepreneur.
These tradeoffs are incredibly difficult to navigate, and most often founder/ceos find they have nowhere to turn. “Your team has no conception of how lonely it is to be the CEO,” says Adam Dell. Or, as Zach Smith, Founder and CEO of Packet, confided:
I used to bring all of my passion, and all of my pain, and all of my frustrations back home to my wife and tell her all about it…and I realized pretty quickly that that actually wasn't beneficial for her or for me…I was really just unloading a whole lot of my context…and its not like she could do anything about it…that's just not how I wanted to spend the time and energy with my partner. So, I stopped doing that…I found other outlets…
As CEO, you alone wield the helm; but you cannot properly serve as CEO by going it alone. Bend your curve by building a CEO support system.
Every pro athlete in the world has a coach. The best have an entire support team of trainers, nutritionists, and recovery specialists focused on helping them perform. CEOs are no different. Here is the team of people that supports you:
Co-founders and key executives: Every CEO deserves co-founders, or 1-2 key executives, that wades through the sh!t with you. For David, it was his CFO Bart, who worked with him for a decade; for Nick, it was his Co-founder and CTO Chis. How you divide responsibilities and support one another matters.
Your spouse or partner: Alignment with, and support from, your partner and spouse - especially if you have children - is critical in navigating the many challenges and pitfalls of entrepreneurship and leadership. Lack of this often ends in divorce or separation (unfortunately this is all too common).
Coach or therapist: For mindset, emotional resilience, and honest feedback that no one else will give you.
Executive assistant and chief of staff: A great EA makes your day go more smoothly, mainly thinking in the present. A great chief of staff makes decisions on your behalf and thinks about the future. Knowing when to hire each (and how to work with them) is part of your growth as a CEO.
Advisors and board members: They’re not just for fundraising. They can be guides, mentors, and sounding boards if you use them well.
Other CEOs: The only people who really understand the job. Peer communities, like the one we run called NY Founders Club, can be a lifeline.
We agree with Nick Mehta, Founder and CEO of Gainsight: when you find yourself with an outstanding support team member “hold on to them with everything you’ve got. Pay them a lot of money, treat them well. Everything you can do for them, do it.”
But remember: like a professional athlete, the help provided by your support system will only be as good as the practices you employ to support yourself. The job of a CEO requires constant context-switching, decision-making, and managing emotions. It is inevitable that you are going to find yourself burned out, and so it is critical that you learn to recalibrate and readjust yourself. As Tony Safoian, CEO of Sada, expresses:
Therapy…therapy is great…I see my guy like once a month. There were times it was more frequent, but keeping a level head, keeping grounded, managing stress, self care, discipline, exercise, diet, especially as you become a parent, you're raising kids...Energy management required to be a great husband, father, and great CEO...it's almost superhuman. So you have to behave as if you're training for the Olympics all the time.
Supporting yourself is a daily practice (and struggle), and includes:
Energy management: How do you step back and slow your mind down? Is it meditation, workouts, cold plunges, solo time, family vacations? What helps you reset and recharge?
Mental and emotional health: You’re not a machine. How do you deal with the inevitable feelings of stress, anxiety, and importer syndrome (among others) that may weigh you down? How do you recognize and deal with these challenges productively?
Boundaries and self-awareness: Knowing when to step back, where to ask for help, and what to say no to.
If you as CEO are not at your best, you cannot possibly lead your company to be its best. Without a support system, it is only a matter of time before you flame out.
Bending your curve: personal and business growth
The stakes of being a CEO are incredibly high. You’re responsible not just for strategy and execution, but for the livelihoods of your team, the expectations (and returns) of your investors, and the long-term health of the company. Every decision you make ripples outward.
You’re juggling it all at the same time. In our experience, and based on conversations with the CEOs we’ve worked with and interviewed, we’ve found that almost everything you’re managing can be mapped back to one of these seven pillars. And it’s rare to have all of the pillars working perfectly at the same time.
Being successful as a Founder/CEO also requires a healthy dose of luck. But as they say, luck is “when preparation meets opportunity”, and so continuously investing in bending your curve as Founder/CEO is critical.
Recognizing where you and your company are weakest is almost always a great place to start. Lean into your strengths, surround yourself with people who can help complement you in other areas, and be brutally honest about where lie the opportunities.
If you have questions, or just want to talk, we are here to help however we can. Just reply to this newsletter. And please stay tuned for more lessons learned, tactical how-tos, and real-world guidance on the 7 Pillars at Not Another CEO.