We asked successful entrepreneurs how they planned their business exits. Here’s what they learned about timing, valuations, and transitioning ownership.
I’ve worked on a number of due diligence projects for major private equity firms that are in the acquisition process for Enterprise SAAS companies. In some cases, these are companies owned by other private equity funds at the end of the hold period, and in others it’s a founding team that is selling the business in part or whole.
Assuming you’ve gone through the process internally of the reasons you’re selling the business and have determined it’s something you want to do (for emotional, financial, life planning, etc., reasons), then the process is typically pretty quick. You might hire a sell-side advisor to help you create a competitive deal environment. They often work with folks like us to do mock diligence so the company understands areas to improve before they go under LOI.
Once that occurs, there is typically a short time period (e.g., 30 days) for the buyer to do diligence across all departments: legal, earnings, commercial, technical, product, etc., and determine the final price, terms, and timing. It’s a fast process and can be emotional. Finding competent, warm, and trustworthy advisors to help you along that journey is key. You’re experts at running the business, but not selling it. My advice is to work with folks you have a good relationship with who will be honest, transparent, and help you understand what’s coming and how to make good decisions. It’s an exciting time in your journey.
Sean Everett
CEO, Evergence
Entrepreneurs often build businesses because they are passionate about solving a problem or fulfilling a dream. However, what they may not realize is that their business can become a source of immense personal pressure and stress, especially as it grows. The decision to exit should directly align with both your lifestyle aspirations and your capacity to handle future risk.
1. Life Goals: What does the future look like for you, beyond the business? Are you chasing financial freedom, personal fulfillment, or legacy?
If financial freedom is your primary goal, an exit now might be appealing
2. Risk Tolerance: Can you handle the stress and uncertainty of growth or potential decline? Are you prepared to take the risk for further growth or prefer stability now?
If you’re feeling burnt out or uncertain about the future, taking the exit now might relieve stress and help you focus on the next phase of life.
3. The Tradeoff: Now vs. Later
Exit Now:
Risk the Future:
Decision: You should ask yourself:
In short, the decision should reflect the founder’s current mindset—whether they are seeking freedom, new experiences, or a legacy—and should acknowledge the trade-offs between taking financial security now or risking more for the potential of greater rewards later.
At the heart of it, the best exit strategy isn’t about maximizing profit, but rather maximizing the alignment between your life goals and your business journey. The timing and choice are deeply personal.
Maddy A
Founder and CEO, Startup to Scaleup
For entrepreneurs considering exiting their business, my advice is to ensure your financials, processes, and team are fully optimized and documented. Buyers look for businesses that can run smoothly without the owner, so creating a strong operational foundation is critical.
Weigh factors like your emotional readiness, the market conditions, and your business’s valuation. When we exited FreeUp, we had clear processes, a strong team, and recurring revenue, which increased its appeal to buyers. Ultimately, consider whether the timing aligns with your personal goals and the potential for the business to thrive under new ownership.
Connor Gillivan
Entrepreneur, Owner & CMO, AccountsBalance
One key piece of advice for entrepreneurs considering an exit is to start planning early, ideally at least three to five years before the intended sale. Many business owners overlook the importance of building a business that can thrive without them, which is critical for attracting premium buyers. Begin by focusing on clean financials, operational efficiencies, and a strong leadership team that can carry the business forward.
An innovative approach few businesses take advantage of is leveraging AI and data analytics to identify and optimize underperforming areas of the business. By integrating these tools, owners can improve margins and demonstrate scalability, significantly enhancing valuation. This proactive, tech-driven strategy ensures a smoother transition and provides entrepreneurs with peace of mind, knowing their business is positioned as a robust, self-sustaining asset.
Charles Dents
Founder and CEO, Xelantt Profit Strategists
For entrepreneurs considering exiting their business, my advice is to treat the process like a real estate transaction: preparation and clarity make all the difference.
Before anything else, I’d suggest understanding the true value of your business. It’s easy to get attached and overestimate, but bringing in a third-party valuation ensures you have a realistic starting point. I’ve seen friends regret not doing this, as it led to underwhelming offers or negotiations that didn’t reflect the business’s worth.
Another important factor is understanding your long-term financial goals. If you’re exiting to pursue another opportunity or retire, think about what kind of payout or ongoing arrangement will help you get there. I’ve seen entrepreneurs successfully negotiate partial buyouts where they stayed on as advisors, allowing them to transition gradually while still reaping the rewards of a sale.
Timing is also critical. Exiting during a strong market cycle or when the business is performing well usually results in higher value.
Austin Rulfs
Founder, Sme Business Investor, Property & Finance Specialist, Zanda Wealth
First off, be real about it. It’s a big decision, and feeling a little nervous is okay.
Before you take this step, ask yourself:
I’ve interacted with some business owners who love the idea of an exit—the financial freedom, the “founder-turned-investor” LinkedIn glow-up.
But the truth? Exits can be bittersweet. It’s messy. It’s emotional.
I’m not saying this to scare you off. In fact, the challenges are what make it transformative.
Lastly, unless you’ve figured out your “why,” the exit won’t feel as fulfilling as it should.
Just take the leap if you have made up your mind. But don’t just like the idea of an exit. Respect it.
Vyom Bhardwaj
Founder & CEO, Muoro
After selling part of my digital marketing agency last year, I learned that timing isn’t just about market conditions—it’s about personal readiness. Start planning your exit at least two years before you intend to leave. This gives you time to strengthen your financial records, streamline operations, and build a team that can run without you. The biggest mistake I see fellow entrepreneurs make is waiting until they’re burned out or facing a crisis before thinking about their exit.
The most valuable advice I can share is this: your business needs to thrive without you before you can sell it. Focus on creating solid systems, documenting your processes, and developing your key staff members. When I was preparing to sell, I deliberately stepped back from day-to-day operations for six months to prove the business could run independently. This not only increased the sale price but also gave potential buyers confidence in the company’s future success. Remember, buyers are purchasing your business’s future potential, not its past achievements.
Adam Haworth
Founder, Contactora
Exiting a business is one of the most significant decisions an entrepreneur can make, and it’s not just about the financial payoff—it’s about personal readiness and long-term vision. My advice is to assess both your emotional and financial preparedness.
First, evaluate if you’re emotionally ready to let go. A business is often a huge part of your identity, and exiting can come with a sense of loss or uncertainty. Ask yourself: Have you reached a point where you feel satisfied with what you’ve built, or is burnout or a lack of passion driving the decision?
Second, consider your financial goals. Is the exit in line with your long-term personal objectives? Make sure you understand the true value of your business and if now is the right time to sell, given market conditions. Timing is critical—both the state of your business and external factors like industry trends or economic cycles can impact the sale.
Lastly, think about the legacy you want to leave behind. How will your exit affect employees, customers, and stakeholders? Will the business continue to thrive without you, or do you need to plan for a leadership transition?
Exiting a business is personal and complex, and it requires reflection on both financial and emotional factors. Take the time to evaluate your readiness, your options, and the future of your business.
Sahil Sachdeva
CEO & Founder, Level Up PR
I always get asked about exiting businesses, and it’s a huge decision that shouldn’t be taken lightly. Money is a factor, but it’s not everything. If you’re just chasing dollars, you might regret selling once the high wears off. Ask yourself: Are you exhausted? Have you lost that spark and hunger to grow the business further? Or are there personal reasons, like wanting to spend more time with family? I would suggest you be clear on your motivations, which is the key.
My biggest piece of advice through my journey is don’t go it alone. Lean on your mentors, advisors, and been-there-done-that entrepreneurs in your network. They’ll give you the real talk on when the right time is to exit based on your unique situation. At the end of the day, it’s a big life decision, not just a business one. So take a beat, get real with yourself on what you want for the next chapter, and make a wise choice for you and your family’s future. In my opinion, an exit can be a new beginning or the final page—the power is yours to write that story.
Nitish Kumar
CEO/Owner, VIPTRO
Digital valuation metrics radically changed our perspective on exit timing. Most SEO agency owners focus solely on revenue, missing the real value drivers like recurring revenue stability and operational scalability. Last year’s market shifts taught us a crucial lesson about exit preparation. We strengthened our SOPs and automated campaign management systems, shifting from founder-dependent processes to scalable operations. This systematic approach not only improved our service delivery but dramatically increased our company’s attractiveness to potential buyers.
Getting your analytics house in order makes all the difference. A potential acquirer digs deep into client retention rates, revenue predictability, and team performance metrics. Having clean, organized data that shows sustainable growth matters more than short-term profit spikes. Smart exit planning starts long before you’re ready to sell. Build systems that let the business thrive without you, track the metrics that matter to buyers, and understand your industry’s unique valuation drivers. The best exit opportunities come when your business runs like a well-oiled machine.
Marc Hardgrove
CEO, The Hoth
If you’re considering exiting your business, I’d encourage you to first explore whether there’s an opportunity to step back without stepping away completely. Exiting doesn’t have to be the only solution; sometimes restructuring, bringing in a strong leadership team, or automating certain areas can reduce your workload while keeping the business thriving under your vision. Before making a final decision, evaluate the true potential of your business. Are there untapped markets, new revenue streams, or opportunities to scale that you haven’t explored yet?
Often, bringing in external advisors, mentors, or even a strategic partner can breathe new life into your operations and help you see growth opportunities you may have overlooked. If personal burnout or shifting priorities are driving your thoughts of exiting, consider delegating day-to-day responsibilities to trusted managers or implementing systems that give you the freedom to step back without completely walking away. A business you’ve built can often continue to thrive under your guidance, even in a more hands-off role.
That said, if exiting still feels right, make sure you’re doing it for the right reasons: timing, profitability, and personal readiness, rather than as a reaction to temporary challenges. Your business might have far more life left in it than you realize, and sometimes the best reward comes from staying the course and unlocking its full potential.
John Talasi
Entrepreneur, John Talasi
For almost every entrepreneur, there comes a time when it seems the best decision is to leave their business. Sometimes this is due to their own fatigue and exhaustion, and sometimes it is due to severe stress and crisis situations. In order to avoid making such a decision impulsively, it is important that you clearly understand why you are doing it. Do you want to keep going, just in a different direction? Or are you simply being pressured by external circumstances? Your motivation should be clear and honest, so that you do not regret your decision in the future.
First, you need to fully evaluate your business to understand the prospects. It is not only about finances, but also about the involvement of your audience, your team. People have supported your journey as an entrepreneur, and it is significant to take that into account when making a decision. Think about how your business will change after you leave and whether you are ready to accept those changes. If you are faced with a lack of customers and strong competition in the market, this is not always a sign that your business does not need to be developed. A loyal audience does not appear immediately, and success does not come on the first day.
Try to immerse yourself in the stories of successful companies that started as small teams and faced a huge number of problems. During a crisis, the stories of Starbucks and Nike inspire me to not give up and keep going. Exiting a company is an important step, not only for you, but also for those who helped build it. I advise you to take time for personal development, communication with other entrepreneurs, and inspiration. This will help you understand the true meaning of your desire to leave. But do not think that this is the end. In fact, it is always the beginning of something new and greater.
Valentin Honcharov
CEO, Claspo
Weigh the long-term potential before making any decisions. I was in a situation where the market was down, and I was just months away from running out of cash reserves, with revenue slipping. But I turned things around by getting creative-cutting costs, investing in advertising, and exploring upselling opportunities. Persistence is key. It’s important to trust in your vision, believe in yourself, and stay resilient through tough times.
Echo Wang
CEO & Co-Founder, EpicBooks
For entrepreneurs considering exiting their business, the key piece of advice is to carefully evaluate whether selling the business or maintaining ownership would yield greater long-term benefits. It’s crucial to recognize that while selling might seem tempting, especially when exhausted from building the business, running and controlling the business could offer more financial stability and potential growth through maximizing profits and revenues.
Consider factors such as tax implications, the potential of reinvesting capital, and the challenges of finding equivalent returns in alternative investments. Additionally, compounding benefits and gaining ultra-wealth through continued ownership could outweigh immediate liquidation benefits.
Remember the importance of strong financial and market understanding when considering an exit. Identifying strategic buyers who can add value to your business might align better with your future plans than just obtaining the best immediate price.
Finally, generally, think about personal goals and lifestyle preferences. The decision should fit within your broader life goals beyond just financial metrics. Balancing these elements ensures that your exit strategy not only serves your business interests but also aligns with your personal life’s aspirations and goals.
John Richards
Managing Partner, Startup Ignition Ventures
