THE INCLINE:
Your Ascent
To Success
Starts Here
Every Great Climber Has a Sherpa - Every Elite CEO Needs a Coach
Even the most skilled climbers don’t conquer mountains alone. They rely on a sherpa - a trusted guide who knows the path, anticipates the challenges, and navigates the toughest parts of the climb.
Scaling your company is no different. The journey is steep, unpredictable, and filled with obstacles that demand expert guidance from someone who’s been there before. As your executive coach, I’ll help you create a strategic roadmap, refine your decision-making, and build a high-performing team that drives sustainable growth.
Every CEO wants their company’s trajectory to go up and to the right—that’s the incline toward a successful exit. Together, let’s make your ascent extraordinary!
Meet Richard Jalichandra,
CEO Coach
If you want to hire a CEO Coach, hire an actual CEO
- 6-time CEO for VC & PE backed companies.
- 2-time founder of profitable bootstrapped companies.
- Specialty: taking over from founders & optimizing to exit.
- Led companies that generated $4 billion of revenue.
- Principal in 40+ M&A transactions worth $2 billion.
- Raised $300 million of debt & equity as CEO, and $1.8 billion as private equity consultant.
- Experience from early stage VC to late stage PE.
- Took 2 pre-revenue companies to 8-figures of revenue.
- Ran 2 large 9-figure P&Ls with 8-figure EBITDA.
- Span of control: largest team - 1,900 employees in 11 countries; smallest team - 18 employees.
- Industry experience: both B2C and B2B in media, publishing, ecommerce, martech, SaaS, manufacturing, supply chain, fitness & professional services.
- Relevant life experience: lived & worked in Asia & Europe for 10 years; traveled to 73 countries; nutrition and fitness expert; practices meditation.
Your Sherpa: The Coach Who’s Been There, Done That
Why Does My Experience Make Me An Exceptional CEO Coach?
Quite simply, because I’ve had more reps than the average CEO!
My background is different from other CEOs who had one or two great success stories for 10-15 years. Instead of running just one successful company, I was the professional exec brought in to work with or take over from founders to grow a company to exit. In quick succession, I fixed, grew and sold 6 companies over two decades (and advised dozens more). And if I’m being honest, most of them were mediocre companies when I was hired, but I quickly turned them around, put them on a path to scale and profitability, and ultimately, to exit. Quite simply, I performed multiple repetitions of all the mindsets, decisions and executions that lead to successful exits.
As the great philosopher Aristotle said:
“We are what we repeatedly do. Excellence, then, is not an act, but a habit".
To learn more about my experience and expertise, visit the About Me section.
Heading towards the exit?
Most entrepreneurs dream about selling their companies someday, and the few that don’t want to pass their companies to their heirs. Unfortunately, most CEOs are not prepared for exit.
- Only 20-30% of small businesses listed for sale ever get sold - even as low as 10% in certain industries.
- Only 48% of business owners have a formal exit strategy, even though 76% hope to sell their company within 10 years.
- Less than 20% have created formal transition or succession plans for their eventual exit.
As your coach, I can help a CEO create an exit plan that ensures a smooth business transition while maximizing value. I’ve worked the M&A game on both sides of the table for strategic acquirers, private equity and public companies - I know how to assess the company, identify key goals, and develop a roadmap for a successful exit - whether through selling or succession.
Having an exit plan in place early allows the CEO to control timing, reduce risks, and seize opportunities when the business is most valuable, avoiding rushed decisions later on. Plus, the preparation process itself simply helps build a better, faster-growing and more profitable company, irrespective of if and when you decide to sell.
Are you a good fit for coaching with me? I work with these types of CEO’s
I love working with companies across the entire growth cycle, from early-stage bootstrapped startups to late-stage private equity-backed enterprises. Having navigated everything from pre-revenue ventures to nearly billion-dollar operations in my own career, I understand the unique challenges and opportunities at each stage. The agility and innovation of early-stage companies inspire me, while the complexity and scale of late-stage businesses ignite my passion for driving strategic, high-impact change. My ability to apply early-stage insights to late-stage challenges - and vice versa - has been a game changer, and now I’m energized by helping leaders at every stage realize their vision.
How do I charge? What are you paying for?
If we decide to work together, you will not be paying me for my time. Rather, you are investing in access to my 30 years of experience. When clients present me with questions, problems or key decisions they need to make, I’ve likely already made those same decisions many times over. You'll get instant feedback and immediately actionable advice - all while also getting the long term strategic thinking you need to build a sustainable path to exit.
Types of Coaching Engagement:
Choose Your Own Adventure
The Incline: Up & To The Right
Designed to help a CEO optimize and grow a company for sustainable growth, and ultimately to exit. 6-12 months initial term, then ongoing with mutually agreed timelines and objectives. With The Up & To The Right Incline, we will work together as athlete and coach to perfect your leadership and management skills while growing your company towards a successful exit.
The Incline: Rapid Ascent
Designed to accomplish a fundamental shift in a CEO’s mindset in a short and finite time frame. 3 months limited engagement. In The Steep Mindset Incline, you’re looking for an immediate change of perspective - one that ensures you don’t miss the forest for the trees. As the coach, I get in and get out, but more importantly, you now have the mindset to see the big picture - which is the difference between incremental growth and truly transformational and disruptive growth.
The Sherpa: 24/7 Coach On Call
For both Up & To The Right and The Steep Mindset, we meet 45 minutes every other week in a regular cadence (the latter also includes one extended strategy session every 6 months - in person or virtually) . In addition to our regular meetings, perhaps the most unique aspect of my coaching is that I am available to you 24/7/365 for quick calls, texts, emails and asynchronous voicemails. In my own experience as a CEO, I found that quick ad hoc questions and 2-minute grock sessions provided as much or more value than formal meetings. Afterall, if it’s a Sunday night at 7pm and you have the idea of a lifetime, you certainly don’t want to wait to discuss until your next session! In short, I want to be available when you need me.
What Topics Do We Discuss?
In addition to working on visionary leadership, decision-making, and personal and professional growth, CEOs need a broad array of strategic and tactical skills. Our 1on1 sessions are tailored to your unique requirements - here are some sample topics:
- The 30-Day CEO Playbook
- The “do no work” objective for every CEO
- The only 3 real to do’s for every CEO
- Profit mindset vs growth mindset
- Leadership development
- Strategic planning
- Tactical planning
- FP&A and financial modeling
- Hiring exec team & key execs
- Leading exec team & board meetings
- Role & responsibility definition
- Systems, process & execution
- Sales team & overall comp structures
- Marketing & advertising strategy
- M&A strategy
- Exit planning
- Business development function
- Product development & technology
- Accountability & Board of Directors function
- CEO therapy & stress reduction - safe space
- Work-life balance
- Personal & professional development
- Big, wild & crazy idea grocking
- Peer groups & CEO communities
CEO Coaching Testamonials
Alan Steremberg, CEO Weather Underground
“Richard was a strategic thought partner and helped me grow as a CEO. He also helped us scale the company towards our eventual acquisition by Weather Channel.”
Tom Kent, CEO Career Nerds
“One of the biggest challenges for bootstrapped companies is understanding the difference between profit mindset and growth mindset. RJ’s coaching has given me a much greater awareness and intention about finding the right balance of both, and on what timeframe.”
Andy Minckler, Managing Partner InsurExcellence
“RJ’s mantra of ‘A CEO’s objective is to do no work’ has enabled me to take myself out of the day-to-day execution and instead focus on finding new opportunities to grow and scale our company. It’s also improved my leadership and my work-life balance.”
Sebastian Schaffer, CEO Dofollow
“Our business was at a crossroads, and we were unsure how to proceed - whether to sell or keep building. RJ quickly helped me clarify and enhance my thinking, and now I’m as excited as ever about our growth prospects.”
Mike Farrar, CFO
“I’m a fractional CFO, and RJ and I have multiple clients in common. I’m always impressed with how RJ works with CEO’s, how he gets them to see into the future to tell the story with words, and then back them up with numbers. He’s also helped me build my fractional CFO practice too.”
Justin Kuykendall, CEO Pulpo Media
“When I founded my company, RJ served as an insightful CEO mentor and an industry expert. He also helped me grow as a leader, and my company achieved great success and an exit.”
Shani Higgins, CEO & Executive Coach
“In my first CEO role, RJ helped me navigate the unique challenges of the hardest job in business. He helped me learn the difference of working on the business versus in the business, which has been critical in my development as a leader and a coach.”
Scott Schwanbeck, CEO Trusted Stack
“RJ has helped me in both of my CEO roles. While he has the requisite experience and expertise, I appreciate his unique perspectives and honest feedback and mentorship.”
Ray Blakney, CEO Live Lingua
“Our company was going through some challenging times, and I was down both professionally and personally. RJ’s experience, expertise and compassion has helped me and my team execute our way back to profitability.”
Larry Weng, Founder & CEO, Phelps United
“I’ve valued RJ’s business and leadership insights for years. As we’ve grown into one of the biggest Amazon services companies, he’s been a great thought partner in helping us plan for our eventual exit.
