Sales isn’t manipulation—it’s service. In this episode, Tiffany-Ann Bottcher and sales strategist Christopher Filiipiack dig into what actually drives consistent revenue in service businesses: courageous, human-first conversations, a clear market/message/offer, and a simple, inspectable sales process. They unpack how to overcome fear of rejection, why founders should stay close to sales, and how to reverse-engineer revenue targets into weekly activity that compounds. If you’ve got a solid offer but inconsistent cashflow, this conversation shows how to turn conversations into clients—without feeling pushy.

What you’ll learn

• Why sales is the real gatekeeper of business success
• Authentic selling = courageous conversations + clear strategy (not scripts)
• A practical way to beat rejection fear and keep momentum
• How to reverse-engineer revenue into pipeline math and weekly actions
• What a “sales-ready organization” looks like (market, message, offer, systems, inspection)
• Why CEO-led selling accelerates learning, positioning, and big-ticket deals

Key takeaways

• Sales is an act of service that helps people get where they want to go
• Conversations > complexity: proximity to buyers beats perfect funnels
• Clarity moves cash: set the number, build the causes, inspect the pipeline
• Design for buyers, not fear: remove hoops that serve you (not them)
• Keep leadership close to the market: insights live in calls, not dashboard

Click here to watch a video of this episode.

About Christopher
Christopher Filiipiackis a sales consultant and coach for CEOs who turns founder-led selling into a scalable advantage. With a background in engineering, data analytics, and Fortune 100 consulting, he blends strategy, execution, and mindset to build Sales-Ready Organizations that sell consistently and profitably. Clients have achieved outcomes such as 12x revenue growth, 500% increases in deal flow, and fivefold growth in client acquisition. His core belief: selling is a loving act done for people, not to them—and when paired with clear strategy and disciplined activity, it creates financial, emotional, and lifestyle freedom.

Resources & links

• Christopher’s site & articles: https://www.christopherfilipiak.com/
• Sales Ready Assessment: https://www.christopherfilipiak.com/sro-assessment

Connect & Subscribe
If this episode helped you rethink sales, follow/subscribe to the Service Based Business Society podcast and share it with a founder who needs a nudge toward courageous, buyer-centric selling.

Creators & Guests

• Tiffany-Ann Bottcher - Host
• Christopher Filipiak - Guest

On this week’s episode of the Service Based Business Society, we’re ripping the bandaid off and mapping the small circle that quietly decides whether you scale or stall. Tiffany-Ann breaks down the six relationships every service-based founder needs: a truth-teller who cuts through the noise, a clean finance stack (bookkeeper → management accounting/CFO → tax strategist), a banker who believes in your vision, the right lawyer at the right time, an insurance pro who matches coverage to real risk, and a mentor plus personal believer to keep you moving when it’s hard. You’ll walk away with a one-page audit to find your gaps, a simple email script to re-engage your banker, and prompts to pressure-test your legal and insurance exposures—so you can make faster, smarter decisions and get to the good part sooner.

Click here to watch a video of this episode.

Creators & Guests

• Tiffany-Ann Bottcher - Host

• Why a single truth-teller can collapse weeks of indecision—and how to invite unvarnished feedback you’ll actually use.
• The finance stack demystified: bookkeeping vs. management accounting/CFO vs. tax—and when each role pays for itself.
• How to sell your vision to your banker so you get better products, higher limits, and a real human who advocates for you.
• When to stick with a generalist lawyer and when risk demands a specialist (plus a simple triage lens).
• The overlooked value of an insurance pro who maps coverage to your actual exposures (not generic checklists).
• The mentor + personal believer combo: one sharpens your strategy, the other protects your stamina.

The Short List: Your Circle of Scale

1. Truth-Teller — cuts through nice-sounding noise
2. Bookkeeper → Mgmt Accounting/CFO → Tax — three roles, three outcomes
3. Banker — a person, not a 1-800 queue
4. Lawyer — generalist for routine, specialist for risk
5. Insurance Pro — coverage matched to reality
6. Mentor + Personal Believer — tactics + resilience

Apply It This Week

✔️ Name your truth-teller: DM one peer/vendor and ask for “the unvarnished version” on your top decision.
✔️ Map your finance stack: Who owns bookkeeping? Who interprets numbers (CFO/analyst)? Who handles tax strategy? Circle gaps.
✔️ Email your banker: Share a 12-month vision + ask, “What would we need in place to qualify for X?” Book a call.
✔️ Legal triage: List your next 3 initiatives; mark which deserve a specialist review and schedule it.
✔️ Insurance pulse check: Write your top 5 exposures (advice liability, subcontractors, vehicles, in-suite work, data). Book a coverage review.
✔️ Mentor & believer: Identify each by name. If missing, shortlist 3 mentors to approach and choose your personal believer (spouse/friend/coach).

If AI were a hire, this episode makes the case that it’s the team member everybody needs—from turning screenshots into calendar invites to booking calls via chat and voice, and even “training” your tools like you train a new employee.

What’s Inside:

• Screenshot → Calendar in one click. James’ “image-to-calendar” GPT converts event screenshots (title, date, time, location) into a Google Calendar URL you can save instantly—no manual entry.
• “Don’t invite your wife” (…unless you want to). How James cloned his GPT—one version auto-invites his wife, the public one doesn’t.
• From reminders to real conversations. HighLevel reduced no-shows with timely texts—and now AI can handle the reply to reschedule or confirm, conversationally.
• AI that books appointments (for real). Why chat and voice bots are already booking, collecting info, and getting people serviced—seeing it live changes everything.
• Choose systems for the right problem. When a client thought they needed job management, the real fix was pipeline automation in HighLevel first.
• Train AI like a teammate. Feed merge-field syntax, brand voice, and “how we say things” so outputs paste straight into your stack—just like coaching a new hire.
• Repurpose like a pro. A video-first workflow: wait for the transcript, then spin out descriptions, social posts, and emails.
• Mind the AI divide. Why $20/month on AI is the new table stakes—and how staying curious keeps you on the right side of change.

Click here to watch a video of this episode.

Resources Mentioned:

Google Calendar GPT
The Marketing Show

About the Guest — James Hurst

Host of The Marketing Show, builder of practical HighLevel automations and custom GPTs that business owners actually use. A two-time ClickFunnels Dream Car winner and 2023 HighLevel Affiliate Bronze award recipient, James blends a software-developer background with hands-on marketing ops to ship clean, scalable systems.

About the Host — Tiffany-Ann Bottcher

Entrepreneur, founder of Bottcher Group, and host of the Service Based Business Society podcast. She blends strategy, systems, and tech to help service businesses scale with sanity.

Creators & Guests

• Tiffany-Ann Bottcher - Host
• James Hurst - Guest

In this episode, Tiffany-Ann Bottcher pulls back the curtain for new and longtime listeners of the Service-Based Business Society podcast. After more than 100 episodes, she reintroduces herself, her journey from scaling a $12M corporate business to building multiple companies under the Bottcher Group umbrella, and the reality of balancing entrepreneurship with a full family life.

Tiffany shares candid insights on why she created this podcast, the evolution of its mission, and how the business landscape—and her own priorities—have shifted through the seasons. From embracing imperfect action (like launching TaxGo mid-season) to navigating the infamous “valley of death” in business growth, she offers an unfiltered look at what it takes to build something meaningful. Whether you’re a first-time listener or a loyal fan, this episode is an invitation to dream bigger, push harder, and build a business that aligns with your life—messy schedules, late-night work sessions, and all.

Takeaways

• Building big businesses requires courage, imperfect action, and resilience.
• Growth brings bigger costs and risks before the rewards catch up.
• Success isn’t about working less—it’s about working smarter and harder when needed.
• Your business should evolve with your life and energy, not the other way around.
• Balancing family, sports schedules, and multiple companies is chaotic—but possible.
• The “valley of death” is a normal part of scaling—push through it.
• Community and strategy matter, but honoring your own limits is essential.
• Passion and vision set the ceiling for what’s possible.
• Done is often better than perfect—real growth happens in action.
• Behind the polished moments, the real story of entrepreneurship is beautifully imperfect.

Creators & Guests

• Tiffany-Ann Bottcher - Host

Resources

Bottcher Group
Path 2 Profit Bookkeeping and Tax
Goal Getter Media
TaxGo
TiffanyAnnBottcher.com

Click here to watch a video of this episode.

In this episode, Tiffany-Ann Bottcher welcomes listeners to Season Five of the Service-Based Business Society podcast, reflecting on her journey as an entrepreneur and the growth she has experienced. She discusses the challenges of scaling a business, the importance of navigating personal and professional growth, and the chaos that often accompanies timing in business. Tiffany emphasizes the significance of managing people and roles effectively, as well as the need for personal health and well-being amidst the demands of entrepreneurship. The episode concludes with a reminder of the renewed energy that September brings, likening it to a new year for business owners.

Takeaways

• Scaling isn't all highlight reels; it's messy and hard.
• Growth in business can lead to growing apart in relationships.
• It's okay to lose sleep over your business if you care.
• The speed of change in business is unprecedented.
• Navigating chaos is part of the entrepreneurial journey.
• Managing people can be the toughest challenge in business.
• Promoting someone can sometimes lead to their unhappiness.
• Personal health should be a priority for entrepreneurs.
• September feels like a new year for business cycles.
• Embrace the chaos and find ways to manage it.

In the final episode of Season 4, Tiffany-Ann Bottcher dives into the chaotic, unpredictable reality of entrepreneurship. From tax season crunch time to spontaneous brand launches and last-minute decisions on vacation, she shares why chaos isn’t a red flag—it’s often a sign you’re building something that matters.

This episode isn’t about chasing a perfect business—it’s about embracing the messy middle, choosing progress over perfection, and learning to lead through uncertainty. Whether you’re knee-deep in deadlines or juggling too many ideas at once, this is your permission slip to keep going, even when it’s not polished. Because when you’re building something that matters, chaos isn’t the obstacle—it’s part of the process.

Key Insights

• Be Obsessed or Be Average: High achievers don’t wait for perfect conditions—they lean into chaos and make things happen.
• You Can’t System Your Way Out of Chaos: Efficient systems are important, but big goals will always bring new, unpredictable fires.
• Entrepreneurs Live by the Deadline: From last-minute tax documents to game-changing decisions made on vacation—urgency is part of the journey.
• Who You Serve Isn’t Always About Industry: It’s about mindset. Tiffany-Ann chooses to serve people doing big things, regardless of their field.
• Start Before You’re Ready: A new brand was quietly launched this season—not fully, but just enough to plant the seeds for future success.

Entrepreneurial Takeaways

• If you’re doing big things, expect discomfort and chaos—it’s a feature, not a flaw.
• Don’t let perfection stop progress. Launch, iterate, and adapt as needed.
• Know your audience: It’s not about industry—it’s about the people who are ready to grow.
• Urgency is real—entrepreneurs often work best under pressure. Lean into it.
• Lay the groundwork today for the wins you want next year.

As Season 4 comes to a close, Tiffany-Ann leaves listeners with a reminder: chaos is part of the climb, and the path to doing incredible things is rarely linear. Thank you for tuning in all season long—Season 5 is already in the works, and it’s going to be big.

This episode is brought to you by Path 2 Profit Bookkeeping visit https://path2profitbookkeeping.io/

Click here to watch a video of this episode.

Creators & Guests

• Tiffany-Ann Bottcher - Host

Timestamps:

00:00:00 - Introduction to the Service Based Business Society Podcast
00:00:27 - Season 4 Finale and Entrepreneurial Firefighting
00:01:47 - Embracing the Deadline Mentality in Business
00:02:00 - Life Lessons from Pony Club and Early Leadership
00:03:29 - Real-World Skills: Communication, Organization, and Growth
00:04:48 - Becoming Last-Minute Out of Necessity
00:05:40 - Identifying and Evaluating Business Priorities
00:06:42 - Be Obsessed or Be Average: Striving for Excellence
00:07:36 - Entrepreneurial Drive and the Nature of Big Missions
00:08:53 - Business is Balance: Crisis Management Within Reason
00:09:44 - Chaos is Inevitable When Doing Big Things
00:11:01 - Unpredictable Events and the Role of External Factors
00:12:33 - Planning a Disney Trip Amidst Tax Season Chaos
00:13:49 - Serving Entrepreneurial Clients Who Thrive on Pressure
00:15:11 - Why Niching Down Isn’t Always Necessary
00:17:19 - Soft Launch of a New Tax Brand
00:19:44 - Strategic Steps for Long-Term Brand Growth
00:22:30 - Systems Can’t Eliminate Chaos—But They Can Optimize
00:23:42 - Accepting and Thriving in Entrepreneurial Chaos
00:24:25 - Season 4 Wrap-Up and What’s Next for the Podcast

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