If I were starting a coaching business today, I'd focus my first 90 days on perfecting what I call the 'Triple Win' approach - identifying a specific problem I can solve, connecting directly with 15-20 potential clients to understand their pain points, and creating one signature solution based on those conversations. Having built my real estate business through relationship-based wholesaling, I've learned that nothing beats direct problem-solving and word-of-mouth referrals. I'd completely ignore building a fancy website, creating unnecessary digital products, or chasing vanity metrics that don't translate to actual clients. Time is better spent mastering your solution than marketing a half-baked offering.
If I were starting a coaching business today, I'd spend my first 90 days laser-focused on identifying the top 3 pain points that keep my ideal clients up at night, then I'd reach out to 50 people experiencing those exact problems for real conversations. In real estate, I learned that horror stories spread fast, but so do success stories when you genuinely solve someone's problem. I'd ignore everything else - the logo design, business cards, and complicated funnels - because none of that matters if you don't know exactly what problem you're solving and for whom.
If I were starting a coaching business today, I'd spend my first 90 days doing what I call 'boots on the ground' research--physically meeting people where they are, whether that's business meetups, community events, or even coffee shops, to understand what's really keeping them stuck. Coming from the Marine Corps and real estate, I know that intel gathering in person beats any online survey or assumption. I'd completely ignore building any kind of online presence or course creation until I had at least 20 face-to-face conversations that revealed patterns in people's actual struggles--because you can't coach what you don't truly understand.
If I were starting a coaching business today, I'd focus my first 90 days on building genuine relationships with just 5-10 potential clients through one-on-one conversations--not selling, just understanding their real challenges. From my 25 years in real estate, I've learned that your reputation spreads faster through quality relationships than any marketing campaign. I'd completely ignore social media content creation and fancy websites initially--those are distractions that keep you from doing the real work of connecting with people who actually need your help.
If I were starting a coaching business again today, the first 90 days would be about proving demand and getting real clients, not building something that just looks good. I'd focus on talking directly to potential clients, understanding the exact problems they're willing to pay to solve, and validating my offer by selling it before overbuilding it. Early on in my agency, the biggest breakthroughs came from sales calls and feedback, not from tweaking logos or websites. I'd ignore branding polish, complex funnels, and any pressure to be everywhere on social media right away. I learned the hard way that a simple offer, a clear outcome, and consistent outreach outperform fancy websites and long content plans. Once I had paying clients and repeatable results, then I'd scale systems and visibility—but in the first 90 days, revenue and proof matter more than perfection.
There are so many tools and opportunities for coaches that were not available when I first started over 23 years ago. First step, Find a targeted niche and focus. Simplify your message around an outcome not the process. Ask yourself "is my niche the type to buy coaching? Can they afford it? Do they want coaching?" Then, get a 1-page website, a calendar link to book consultations, start with 1 social channel that you use often to showcase some videos, tips and have a place on that platform, send an email and introduce yourself to friends and family as a coach. Ask them to refer you clients, share your excitement. Find places that your ideal clients are and put yourself in the way of them. Network with professionals that also serve your ideal client and ask for referral exchanges. Offer to do a free talk at a bookstore, yoga center or at a professional office to introduce your work. There is no right way to get clients you have to find tactics that fit your personality and that you love - have fun! If you hate social media, forget it. If you love in-person focus on that. The most critical thing you can do in the first 90-days is hire a coach and work on your MINDSET. Success is 100% mindset, not marketing. I am not talking about vision boards or simple positive thinking, but inner work to face the emotional obstacles that keep you from being successful. This is worth its weight in gold. Not one specific tactic made a difference for me, it was always a shift in inner psychology that led to more success. Every uplevel preceded with a major inner breakthrough not an outer magical tactic. Overall, keep it simple. Don't overwhelm yourself or act in a hurry. Trust that the people you want to serve are out there looking for you and you will find them.
If I were starting a coaching business again, I'd spend the first 90 days proving real value to a handful of clients before worrying about scaling. When I launched my real estate business, I built trust by solving one seller's problem at a time--word spread from there. I'd ignore building fancy systems or automated funnels and instead focus on creating a simple, repeatable process that delivers clear results for real people.
If I were starting a coaching business today, I'd spend my first 90 days finding three people who desperately need help and delivering results for free--just like when I first started flipping houses with my brother, we had to prove ourselves before anyone would trust us with their property. From my football coaching experience, I know that one player's transformation on the field speaks louder than any playbook you could write. I'd ignore everything about building a 'coaching brand' or creating programs--instead, I'd focus entirely on becoming known as the person who shows up and gets things done, because that's what actually builds a sustainable business.
If I were starting a coaching business today, I'd focus my first 90 days on establishing a transparent value exchange--exactly as I do in real estate--by listening to prospects' challenges and creating immediate, actionable solutions tailored to their specific situations. From my decades helping homeowners navigate complex transitions, I've found that demonstrating empathy and problem-solving ability in real time creates far more trust than any marketing strategy. I'd completely ignore building elaborate systems or sales funnels, and instead concentrate solely on becoming the person who makes complex situations simple for a small group of ideal clients who will become your most powerful advocates.
I would use the same roadmap I used when I started my own coaching business, which helped me build a six-figure business in four months and quit my 9-5. I'd focus my first 90 days on one specific problem for one specific audience using a skill I already have. I'd use online groups (such as Facebook, Slack, or LinkedIn) to provide value by answering questions and helping people. I personally used what I call the Free Taster Strategy, which essentially is a free coaching call to give people a quick win so they see the value in your coaching. I would also only focus on these types of actions that get you in front of the right people and ignore things like setting up a website or funnels (those come later). You don't need a brand to get your first three clients; you just need an offer that solves a big problem.
If I were starting over, those first 90 days would be all about manual validation. Forget everything else. You need high-touch delivery. I'd spend every waking hour having direct conversations with potential clients. You have to find that one specific, high-value problem they're desperate to solve right now. Don't fall for the "scale" trap. You don't need a fancy brand, complex automation, or some expensive tech stack. We've seen it time and again in our research: coaches hit a wall because they over-engineer their platform before they've even proven people want what they're selling. My only goal would be getting three paying clients. That's how you prove the unit economics actually work. If you can't deliver real results with a simple video call and a shared document, no amount of software is going to help you scale later. Starting a service business is about the strength of the relationship, not the sophistication of your tools. It's way too easy to hide behind "building" something because the real work--the selling and the delivering--is harder. Focus on the human outcome first. The rest can wait.
If I were starting over, I'd spend the first 90 days prioritizing fast, honest feedback from real people--whether that's jumping on calls with past contacts or reaching out to folks in my network who face complex real estate issues. In my experience, you learn the fastest by helping someone solve an actual problem and then asking them what mattered most about your approach. I'd put off group coaching launches, webinars, or anything that takes me away from those gut-level, one-on-one conversations--because every business I've built started with a few people whose trust I earned by meeting them where they needed help most.
If I were launching my coaching business today, I'd dedicate my first 90 days to creating what I call 'case study partnerships' - identifying 5-7 individuals going through high-stakes transitions that mirror the real estate distress scenarios I specialize in. Just as I'd approach a homeowner facing foreclosure, I'd focus on co-creating highly personalized exit strategies through deep listening, removing barriers (like mental roadblocks instead of physical ones), and delivering tangible pressure relief. What I'd ignore? Absolutely anything that doesn't involve direct problem-solving conversations - webinar scripts, CRM tweaking, or perfecting 'scalable' systems can wait until you've proven you can turn someone's impossible situation around.
If I were starting a coaching business today, I'd spend my first 90 days identifying clients with what I call 'distressed situations'--those complex, high-stakes challenges others walk away from--and apply my credit analysis skills to dissect their root causes and craft personalized solutions, much like I do for homeowners facing impossible sales. I'd completely ignore standardized coaching frameworks and mass-audience webinars because real breakthroughs happen when you treat each client's chaos as a unique puzzle that demands creative, boots-on-the-ground problem solving.
If I were starting a coaching business today, I'd focus my first 90 days on applying my analytical skills to truly understand client pain points while bringing the same empathy I use in probate situations. In real estate, I've learned that blending data with genuine human connection creates the most value--I'd conduct 15-20 in-depth interviews with potential clients to identify patterns in their challenges before creating any offerings. I'd completely ignore building complex systems or chasing client volume, focusing instead on creating a transparent, stress-free process for a small group of clients who need the most help navigating their transitions.
Executive Coach (PCC) + Board Director (IBDC.D) | Award-Winning International Author at Capistran Leadership
Answered 2 months ago
First 90 Days: What Matters, What Doesn't If I were starting a coaching business today, the first 90 days would be all about clarity and connection. I'd spend my time figuring out exactly who I serve, what keeps them up at night, and how I can actually make a difference. That means talking to real people—potential clients, mentors, peers—hearing their stories, testing whether my ideas land. You learn a lot more from those conversations than from fancy slides or polished marketing. I'd also make sure there's a system for keeping track of the important stuff—prospects, commitments, referrals. Nothing over-complicated. Simple habits that you can repeat consistently beat tools or software any day. What I'd ignore? Noise. The social media trends, the over-engineered branding, chasing clients who don't fit just to hit a number. Early success isn't about doing more. It's about doing right. The clients who truly resonate with your work? They become your best advocates. They carry your credibility further than any campaign ever could. In short: spend those first 90 days listening, refining, connecting. Everything else—everything that doesn't move the needle on clarity or real client relationships—can wait.
If I had to do it all over again, I'd dedicate those first 90 days to getting out in my local community--attending meetups, volunteering, and asking loads of questions about what keeps people up at night in real estate or entrepreneurship. There's no substitute for face-to-face honesty when you're building trust--it's how I found my first investment deals, and it's just as effective for coaching. I'd put zero energy into polished marketing or complex programs until I'd truly walked in my clients' shoes and earned those first few testimonials from people whose lives I improved firsthand.
If I were to start a coaching business again, the first 90 days would be spent on establishing priorities and creating a rhythm of reviewing progress. I would focus on the activities that have the greatest impact and create a system of accountability and open communication with early clients. I would focus on progress and make changes based on what is happening. I would not focus on activities and opportunities that do not contribute to the established priorities.
If I were starting a coaching business today, I'd dedicate the first 90 days to proving genuine impact by helping a few real people through situations I understand deeply--just like when I started Sierra Homebuyers by walking homeowners through tough decisions one-on-one. I'd keep it simple: listen closely, deliver results, and document those wins as proof of value. I'd ignore logo design, ad spend, and social media noise until I had undeniable stories of transformation that speak louder than any marketing ever could.
If I were starting a coaching business today, I'd dedicate my first 90 days to hosting neighborhood coffee roundtables and volunteering at local business events--exactly how I discovered my first real estate clients--to identify entrepreneurs facing legacy-building challenges. By solving one community member's complex transition problem hands-on, like helping a family business transfer ownership smoothly, you become the trusted advisor others seek organically. I'd completely ignore national advertising or digital blasts because hyper-local presence builds credibility faster than any algorithm when you're known as the person who shows up where it matters.