Rain or Shine | Marketing & Entrepreneurship Podcast

Kelsey Reidl | Business & Marketing Coach
  • 5.0 (16)
  • Entrepreneurship
  • Updated Biweekly

Rain or Shine isn't just a cute motto you slap on a coffee mug. This is your new operating system. Rain or Shine has been my personal guiding phrase for over a decade, and it acknowledges that there are going to be rainy days.. For all of us, in all seasons. So instead of wallowing in them, why not plant some seeds. Splash in puddles. Know that the sunshine is on its way. Rain or shine also means, lacing up for that 6am run you promised yourself, even when it's pouring and your bed feels like a warm hug. It's hitting publish on that podcast episode, blog post, or business idea even when your inner critic is screaming "it's not perfect yet!" It’s about recalibrating our minds to see that the rainy days are part of life, they are a necessary balance to the sunny days, and to fear them or try to avoid them is just blindness to how the world works. If there’s one quick secret I can share with you before we begin, it’s that consistency beats perfection every …single… time. And the entrepreneurs who WIN aren't the ones who only show up when they feel like it — they're the ones who build the muscle of showing up, even on rainy days.

  1. 9h ago

    411 SEO for Small Businesses: Google Rankings, AI Search, and Getting Found Online with Matt Diamante

    Quick Summary Matt Diamante — founder of the Hey Tony Agency — joins host Kelsey for a candid conversation about his winding path from process server to band member to SEO expert. Matt breaks down the foundational steps any small business owner can take to rank on Google, explains how AI search is changing content strategy, and shares the simple daily habit that transformed his referral-only agency into a content-driven machine. In This Episode How Matt accidentally fell into marketing while trying to promote his bandThe unusual jobs (process server, film crew) that shaped how he runs his agencyGrowing an alternative lifestyle blog from zero to 4 million monthly visitors — and what it taught him about hooksThe origin story behind the name "Hey Tony"The three SEO fundamentals every small business needs: Google Business Profile, a multi-page website, and topical authorityWhy most SEO vendors are scamming small businesses — and how to protect yourselfThe AI prompt Matt uses to write unique, expert-driven blog posts in one hourHow SEO is evolving in the age of ChatGPT and AI search enginesWhat two books pushed Matt to post on social media every single day in 2023Why he doesn't batch content — and why he thinks you shouldn't eitherKey Takeaways Every page on your website is a door. Service-based businesses should have a dedicated page for every service they offer. If Google doesn't see it, it doesn't know you offer it.Use AI to extract your expertise, not replace it. Instead of asking ChatGPT to "write a blog post," prompt it to interview you with 10 questions and answer in voice mode. The result is genuinely unique content that reflects your experience.Get to the point faster. In the age of AI search, content that buries the answer under a long preamble will lose. Lead with the answer, then go deeper.Reviews require a system, not willpower. Build a consistent ask into every completed transaction. You can incentivize leaving a review — just not a five-star one specifically.Consistency beats perfection. Matt went from 4 hours per video to 5–10 minutes by posting every single day. The skill builds. The ideas flow. Just start. Memorable Quotes "I believe the world is built on small businesses. If I can help good people grow through SEO, they can hire more staff, create jobs, send their kids to college. If I want to make the world a better place, I can do that one small business at a time." — Matt Diamante"SEO is just solving somebody's problem. How do I fix this myself? That's a blog post. How do I hire someone? That's a service page." — Matt Diamante"That's basically how you run a business. You set up a printer in your car and you figure out how to do this more efficiently." — Matt DiamanteResources Mentioned Instagram: Search @heytonyagency or Matt Diamante???? Get Found by Matt Diamante — Matt's plain-English SEO book for small business owners???? The One Thing by Gary Keller & Jay Papasan???? Jab, Jab, Jab, Right Hook by Gary Vaynerchuk???? AnswerThePublic.com — tool for finding customer questions to write blog posts around???? ChatGPT / Claude — recommended AI tools for blog post creation???? Hey Tony Inside — Matt's community for small business owners doing their own SEO???? Google Business Profile — free local SEO tool for any brick-and-mortar or service-area businessAbout the Guest Matt Diamante is the founder of Hey Tony Agency, a Canadian digital marketing agency specializing in SEO for small businesses. After growing an alternative lifestyle publication to 4 million monthly visitors, Matt channelled those hard-won content lessons into building an agency, a community, and a book — all aimed at helping small business owners get found online without getting scammed. He has posted on social media every single day since January 2023.

    44 min

  2. Jun 8

    410 4 Mindset Shifts That Separate Junior Entrepreneurs from Experienced Ones (And How to Close the Gap)

    Quick Summary In this candid solo episode, Kelsey Reidel breaks down four mindset shifts she's observed over nearly a decade in business — distinctions that separate entrepreneurs who stay stuck from those who keep growing. Inspired by a morning hike and a Marco Polo conversation with two long-time entrepreneur friends, Kelsey shares real scenarios, personal stories, and honest reflections on what it actually takes to build a sustainable business. In This EpisodeWhy "junior" vs. "experienced" has nothing to do with how long you've been in businessThe real purpose of your first event, launch, or marketing experiment (hint: it's not profit)Why experienced entrepreneurs still slide into DMs — and why you should tooHow to turn every "no" into a source of intelligence rather than a source of shameThe emotional regulation strategies that keep seasoned entrepreneurs from spiraling when things go sideways Key Takeaways Your first event is a research project, not a revenue event. Kelsey grew her events from 10 women in a free coffee shop to 80 women at a sold-out, fully sponsored venue — one small step at a time. Start with three people if you have to.The unscalable work is where the business actually gets built. No matter how big your email list, DMs, coffee chats, and personal follow-ups still move the needle. The most successful entrepreneurs never stop doing this work."No" means "not yet" — treat it like data. Every objection tells you something your messaging isn't addressing. Get curious instead of shutting down.One hard week isn't a business crisis. The experienced entrepreneur has systems to process difficult events without letting them derail the entire plan.You are your business's biggest cheerleader. The moment you start to believe it's not working, your revenue reflects it. Protect your confidence fiercely. Memorable Quotes "Hosting your first event is never about profiting on day one. It's about brand-building, visibility, relationship-building, and market research — all rolled into one.""The experienced entrepreneur never outgrows the unscalable stuff. They just get more intentional about it.""When people say no, it usually means 'not yet,' or 'I don't have the information I need.' Get curious — don't shut down." Resources Mentioned Kelsey’s Website: KelseyReidl.comKelsey’s Instagram: @KelseyReidlChicka Chicka Boom Boom by Bill Martin Jr. & John Archambault — Kelsey's go-to reminder that it's A to B, not A to ZMarco Polo app — Kelsey's favourite tool for voice-note conversations with business friendsRain or Shine event in Prince Edward County — July 17th (details on Kelsey's Instagram)About the Host Kelsey Reidl is an entrepreneur, fractional CMO, and host of Rain or Shine (formerly Visionary Life). She's been podcasting for 8 years, helping entrepreneurs show up consistently and build sustainable businesses. She runs the Wave Mastermind and specializes in marketing strategy, website design, and business growth. Kelsey is a mom to a 2-year-old, an avid mountain biker, and a firm believer in the "rain or shine" mentality.

    28 min

  3. Jun 1

    409 From Café Owner to Lawyer at 40: Sonya Szabo on Reinvention, Visioning, and Building a Business on Your Own Terms

    Quick Summary Sonya Szabo is a Canadian business lawyer, former café owner, and entrepreneur who has never done things the conventional way — and that's exactly why it works. In this episode, she returns to the Rain or Shine podcast after eight years to share the full arc of her story: building and selling the Vic Café, going to law school at forty, battling imposter syndrome, and ultimately creating a law practice that reflects her values instead of the industry mold. In This Episode How Sonya opened the Vic Café at 35 with three kids — and led with boundaries from day oneWhy she hired a manager before opening the doorsThe highs and hard realities of running a brick-and-mortar restaurant for eight yearsGoing back to law school at forty and navigating four years of imposter syndromeThe "90-year-old self" exercise Sonya uses to make every major decisionHer "quit week" in 2025 — what triggered it and what brought her backWhy in-person relationship-building has been her most effective marketing strategyWhat Zebo Law does and how to work with Sonya Key Takeaways Know your priorities before you open your doors. Sonya put a note in her very first employee handbook that said she was a mom first — and that transparency set the tone for every working relationship that followed.Build the business around your strengths, not your job description. She hired a manager before opening and stayed focused on owner-level decisions from the start.Your vision isn't a prediction — it's a decision-making filter. Sonya doesn't hold her vision because she expects it to happen exactly as planned; she holds it because it tells her what to say yes and no to.Think about your ninety-year-old self. When you filter decisions through who you want to be at the end of your life, the noise clears fast.A "quit week" isn't the end — it's a signal. Panic means something isn't working. Go back to your values before you go anywhere else. Memorable Quotes "Before we even opened our doors, we hired a manager. Traditionally that would have been the owner's job — but I knew I needed to outsource that and just be the owner.""When I hold a decision up against my vision and ask, 'Will this bring me closer to where I want to go?' — the answer tells me whether to say yes or no.""When people started connecting me and 'lawyer' together, you could see the relief on their faces — like, finally, a lawyer who doesn't make me feel belittled. Someone who makes me feel empowered." Resources Mentioned The 7 Habits of Highly Effective People by Stephen R. CoveyThe E-Myth by Michael E. Gerber (referenced)Sonya's Instagram: @askmeaboutcontractsSonya's Website: sonyaszabo.comKelsey’s Website: KelseyReidl.comKelsey’s Instagram: @KelseyReidlFirst Rain or Shine episode featuring SonyaVoxer app — walkie-talkie voice messaging About Sonya Szabo Sonya Szabo is a Canadian business lawyer and the founder of Zebo Law, where she helps entrepreneurs and business owners navigate contracts, corporate structure, trademarks, and more — in language they can actually understand. After eight years running the Vic Café in Prince Edward County and selling it in 2023, Sonya went to law school at forty and built a practice rooted in her own experience as a founder, parent, and entrepreneur.

    38 min

  4. May 25

    408 Marketing Q&A: How to Price Your Services, Evaluate PR Opportunities, and Build an Instagram Strategy That Actually Converts

    Quick Summary In this candid solo session, Kelsey answers your top marketing questions — covering pricing strategy, how to evaluate cold PR pitches, and what to do when your Instagram feels scattered and purposeless. Woven throughout are honest life updates: navigating her second pregnancy, the power of accountability, and how to embrace change as an entrepreneur. In This Episode Why accountability partners (and assistant nudges) are the secret to getting things doneHow pregnancy #2 has looked very different — and why Kelsey is packing her calendar before mat leaveDebating winter babies vs. summer babies (she genuinely wants your input)The Picasso story and what it teaches you about price vs. valueHow to know if your prices are too low, too high, or just rightThe truth about cold pitch emails — when to say yes and when to runA step-by-step Instagram strategy for business owners who feel scatteredThe four-part Instagram sales funnel: Create, Connect, Collect, ConvertWhy showing up imperfectly beats waiting for perfect every timeKey Takeaways Accountability changes everything. You'll cancel on yourself, but you won't cancel on someone else. Use that psychology intentionally — schedule with others, hire coaches, or create external check-ins to move your biggest projects forward.Pricing is a gut check. If you feel undervalued after every transaction, your prices are too low. If you feel like you're ripping someone off, they may be too high. When it feels like a mutual exchange of value — you've nailed it.Evaluate cold pitches with your wallet and your gut. Only pay for media opportunities you're 100% okay losing. Ask for traffic stats, audience demographics, and backlink terms. Some are incredible; many aren't.Brand pillars create consistency. Before you open Instagram again, define 3–4 content pillars — at least one professional, one personal — and some rules for what you won't post. Decision fatigue is the enemy of consistency.Don't stop at "create." Most business owners post and walk away. The real magic is in connecting with your audience, collecting intel on what they need, and then actually making an offer. Memorable Quotes "Picasso was pricing based on his value. He's put in thousands and thousands of hours — so to charge on an hourly basis simply does not make sense.""Once you make that leap, you can then decide: is this the right place for me, or do I need to keep moving forward? That's what you do through life — you just keep turning the next page.""The ratio of people who show up and create good content is probably 1% of Instagram users. The people who want to consume? Probably 99%. So yes, it feels competitive — but the opportunity is massive." Resources Mentioned Kelsey’s Website: KelseyReidl.comKelsey’s Instagram: @KelseyReidlInstaSales Course — Kelsey's four-hour Instagram sales funnel course (free for podcast listeners — DM "InstaSales" to @kelseyreidell on Instagram)Wave Mastermind — Kelsey's business mastermind communityYahoo! News — Referenced as an example of a paid media placement that converted to high-ticket clients About the Host Kelsey Reidl is an entrepreneur, fractional CMO, and host of Rain or Shine (formerly Visionary Life). She's been podcasting for 8 years, helping entrepreneurs show up consistently and build sustainable businesses. She runs the Wave Mastermind and specializes in marketing strategy, website design, and business growth. Kelsey is a mom to a 2-year-old, an avid mountain biker, and a firm believer in the "rain or shine" mentality.

    35 min

  5. May 18

    407 How Adam Morka Grew Trail Hub 170% Year-Over-Year Event Marketing, Digital Strategy & Brand Building in the Outdoor Recreation Industry

    Quick Summary Adam Morka is the entrepreneur behind Trail Hub, a 142-acre events and recreation destination in Durham Region, Ontario built on the site of a former ski hill. In this episode, Adam breaks down how he drove 170% year-over-year revenue growth using a multi-channel marketing strategy, the hard lessons that came with scaling fast, and why his bet for 2026 is simple: elevate your brand. In This Episode How Adam's background as a professional mountain bike racer and Olympic-athlete coach shaped his entrepreneurial mindsetThe morning routines and calendar blocking habits that keep Adam performing at a high level — even on two hours of sleepWhy content marketing and digital visibility are non-negotiable for any business or professional in 2026The step-by-step marketing strategy behind Trail Hub's triple-digit year-over-year growthWhy event marketing is one of the best ROI-generating strategies available (with a real-world case study from supplement brand BPN)The operational growing pains that come when marketing works too wellAdam's one-word marketing bet for the next 12 months: brand elevation Key Takeaways Schedule everything that matters. Adam's morning workout, family time, and personal development are all on his calendar — not left to chance. If it's not scheduled, it's not a priority.Marketing results lag behind effort. Trail Hub didn't see significant impact from their revamped digital marketing until 6–12 months after launch. Set realistic expectations and stay consistent.Event marketing pulls double duty. Well-executed events can run at break even or a profit AND generate content and brand awareness that keeps paying off long after the event.More impressions, fewer conversions. Most businesses convert only 2–2.5% of website traffic. Trail Hub hit 10% — but it required 375,000 annual website visits to get there. Volume of impressions matters.Elevate your brand deliberately. Consumers in 2026 are investing in brands they share values with. Get clear on who you are as a brand and constantly raise the bar — your marketing spend becomes more efficient and your customer quality improves. Memorable Quotes "If everything matters, nothing does. If everything is a priority, then nothing is a priority. — Adam Morka (referencing Alex Hormozi)""The standards you hold your organization to are essentially the business you create — the same way the standards you hold yourself to create the life you live. — Adam Morka""Event marketing truly is one of the best marketing spends a business owner can make. If you do it properly, you can run the event at break even or a profit — and you're also getting the content and awareness out of the event itself. — Adam Morka" Resources Mentioned LinkedIn: Adam MorkaInstagram: @adammorkaTrail Hub: trailhub.caKelsey’s Instagram: @KelseyReidlKelsey’s Website: KelseyReidl.comHubSpot — CRM and email marketing platform used at Trail HubBloom — paid media marketing agency (Toronto & Montreal)BPN — supplement company; referenced as an event marketing case studyThe Four Burner Theory — framework for life prioritizationAlex Hormozi — entrepreneur and author; quote referenced About the Guest Adam Morka is the driving force behind Trail Hub's explosive growth, bringing over a decade of experience spanning professional mountain bike racing, Olympic-level athlete coaching, and tech company scaling. He joined the family business in May 2023 and has since grown revenue by triple digits year-over-year through a relentless focus on digital marketing and brand building.

    39 min

  6. May 11

    406 Pregnancy Q&A: Miscarriage, Announcing at 20 Weeks, and Postpartum as an Entrepreneur with Jodie Muir of Root and Bloom Therapy

    Quick Summary: Kelsey sits down with Jodie, founder of Root and Bloom Therapy, for an honest, heartfelt pregnancy Q&A. They cover everything from why Kelsey waited 20 weeks to announce, to the emotional weight of miscarriage, the art of letting go when you're a type-A entrepreneur, and what intentional postpartum self-care really looks like the second time around. In This Episode: Why Kelsey waited until 20 weeks to announce her second pregnancy — and the business fears behind the decisionThe fear of losing clients when you announce a pregnancy as a self-employed entrepreneurKelsey's miscarriage journey and the conception story she wasn't expectingThe importance of "sitting in the pit" with someone rather than rushing past griefWhy her second pregnancy has felt completely different from her firstPreparing mentally and emotionally for birth and postpartum — with a toddler in the mixNavigating the relationship with her son Freddy during this major family transitionKelsey's worries this time vs. last time: what's changed and what hasn'tOutsourcing and asking for help — finallyPostpartum self-care rituals: the daily micro-moments that actually make a difference Key Takeaways: You don't owe anyone your news in real time. Holding sacred moments close — pregnancy, health, family milestones — is a boundary, not a secret. Processing privately first is a gift you give yourself.Surrendering control isn't weakness — it's wisdom. In fertility, in business, and in parenting, the outcomes we most want rarely come from forcing them.Grief deserves a witness, not a fixer. When someone is in the pit, what they often need most is someone willing to come sit in it with them — not offer a ladder too soon.Know your joy list before the fog sets in. Write down the five to ten micro-moments that fill your cup before postpartum arrives, because you won't remember them when you're in the thick of it.Values aren't static — and that's okay. Checking in weekly with what this season is asking of you is more sustainable than rigidly holding one set of priorities. Memorable Quotes: "It was never a secret — there are just parts of life so magical that you want to hold them tight to your heart for a little bit." — Kelsey"Sometimes what you need is for someone to come into the pit and sit in the pit with you — not try to make you feel better, just help you not feel so alone." — Jodie"Going back four months, I would not have chosen to process all of that by myself. It was a lot of unnecessary rumination." — Kelsey Resources Mentioned: Root and Bloom Therapy: rootandbloomtherapy.caRoot and Bloom on Instagram: @rootandbloomtherapyservicesKelsey’ Instagram: @KelseyReidlKelsey’s Website: KelseyReidl.comKelsey's newsletter: kelseyreidl.com/newsletter"Surviving Life with a Toddler" Workshop: End of June in Brantford (in partnership with Grant Kids Therapy) About the Guest: Jodie Muir is the founder of Root and Bloom Therapy, offering individual and couples therapy with specialized training in perinatal mental health — all things pregnancy, postpartum, and parenthood. She is passionate about helping people navigate the emotional complexity of expanding their families, and recently launched workshops in the Brantford area for parents of toddlers.

    57 min

  7. Apr 27

    405 Behind the Scenes of Our Biggest Event Ever: What Worked, What Flopped, and What's Next for Wave

    Quick Summary Fresh off their biggest event yet — an 80-woman gathering that left attendees floating out of the venue — Kelsey and Em sit down for an honest, behind-the-scenes debrief. From what went wrong to what made it magical, they share the real story of growing Wave Live Events with heart and intention. In This Episode How to resource yourself (and your household) in the week before a big eventThe mindset shift that kept them grounded when things went sidewaysThe biggest level-ups from past events — including finally taking up space on their own stageWhy their event feels different from every other women's networking eventFunny behind-the-scenes moments: construction, agenda glitches, and rolling with itHow their kids stuffed every swag bag — and what that means about building a businessPost-event processing: the crash, the recovery, and the lessons carried forwardWhat's coming next for Wave: micro events, new cities, and protecting the community's soul Key Takeaways Protect your energy before a big event — Have an honest conversation with your support system early. Ask for help before you desperately need it.Presence over perfection — The most valuable thing you bring to your event is your energetic presence, not a flawless run-of-show.Asking for help is a level-up, not a weakness — Delegating details lets you zoom out, see the big picture, and show up better.To teach women to take up space, you have to take up space yourself — Stop hiding behind other people's stages. Your community wants to hear from you.Heart-centered beats ego-forward every time — Five deep connections at an event are worth more than 45 business cards you'll never remember. Memorable Quotes "There is no perfect time for anything. You just have to do it.""If we're teaching other women to take up more space, we need to be taking up more space ourselves.""You leave some events feeling more disconnected than when you arrived — even in a room of a hundred people. We never want Wave to be that." Resources & References Mentioned Kelsey’s Instagram: @KelseyReidlKelsey’s Website: KelseyReidl.comEmily's Instagram: @itsemilyelliotWave for Women Instagram: @waveforwomenWave Live Events — two signature events per year + upcoming micro/pop-up eventsLocations coming: Ontario towns, Ottawa, BC, Prince Edward County About Your Hosts  Emily is a mindset coach and co-founder of Wave for Women, passionate about helping female entrepreneurs feel seen, confident, and connected. Kelsey brings an events background and a natural gift for gathering people, building rooms where women can go deep, do business together, and walk away transformed.

    28 min

  8. Apr 21

    404 Why Marketing Feels Harder Than Ever for Small Business Owners in 2026

    Quick Summary If marketing feels more confusing than ever, you’re not imagining it. In this episode, Kelsey breaks down why so many female entrepreneurs feel overwhelmed by modern marketing, what “scatterbrain marketing” is costing your business, and why community-based strategies are making a major comeback. She also shares how AI search is changing discoverability, why your digital footprint matters, and how to simplify your next growth season. In This Episode Why marketing feels harder in 2026The trap of scatterbrain marketingWhy old-school relationship marketing works againHow to choose the right platform for your businessUsing 90-day marketing experimentsWhy your website + online presence still matterHow ChatGPT is changing business visibilityFinding the right keywords naturallyWhy community builders will win the futureKey Takeaways More tactics do not equal more growth.Start with your goal before choosing platforms.Use 90-day tests instead of emotional overcommitment.AI rewards clear positioning and trust signals.Relationships are becoming your greatest marketing asset.Memorable Quotes “The future belongs to community builders.”“You do not need to do everything. You need to do the right things.”“People are tired of the information economy. They want the connection economy.”Resources Mentioned Kelsey’s Instagram: @kelseyreidlKelsey’s Website: kelseyreidl.comChatGPTGoogle Search ConsoleGoogle AnalyticsLinkedInInstagram About the Hosts Stacy Millard is a CPA, entrepreneur, and the founder of Thrive Accounting, a firm dedicated to helping entrepreneurs experience more joy and freedom in business through strategic financial guidance. After successfully scaling and selling her first accounting firm for seven figures, Stacy returned to entrepreneurship to build a values-aligned business focused exclusively on serving fellow business owners. She hosts the Small Business School podcast and is passionate about community, financial transparency, and helping entrepreneurs understand the real numbers that drive business success. Kelsey Reidl is an entrepreneur, fractional CMO, and host of Rain or Shine (formerly Visionary Life). She's been podcasting for 8 years, helping entrepreneurs show up consistently and build sustainable businesses. She runs the Wave Mastermind and specializes in marketing strategy, website design, and business growth. Kelsey is a mom to a 2-year-old, an avid mountain biker, and a firm believer in the "rain or shine" mentality.

    43 min
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About

Rain or Shine isn't just a cute motto you slap on a coffee mug. This is your new operating system. Rain or Shine has been my personal guiding phrase for over a decade, and it acknowledges that there are going to be rainy days.. For all of us, in all seasons. So instead of wallowing in them, why not plant some seeds. Splash in puddles. Know that the sunshine is on its way. Rain or shine also means, lacing up for that 6am run you promised yourself, even when it's pouring and your bed feels like a warm hug. It's hitting publish on that podcast episode, blog post, or business idea even when your inner critic is screaming "it's not perfect yet!" It’s about recalibrating our minds to see that the rainy days are part of life, they are a necessary balance to the sunny days, and to fear them or try to avoid them is just blindness to how the world works. If there’s one quick secret I can share with you before we begin, it’s that consistency beats perfection every …single… time. And the entrepreneurs who WIN aren't the ones who only show up when they feel like it — they're the ones who build the muscle of showing up, even on rainy days.

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