Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

In this special Collab Week episode of Wantrepreneur to Entrepreneur, eight founders answer one deeply personal question:
What would you say in a voicemail to your younger self?
You’ll hear from Lisa Larson, Jane Alexander, Nate Hebbert, Nicholas Cook, Mike Gross, Leslie Hemedes, Shawn Sundsvold, and Stephen Custer as they look back on the earlier versions of themselves — the ambitious ones, the scared ones, the grieving ones, the overthinking ones, the waiting ones, and the ones who had no idea how much life and business would eventually teach them.
This episode is full of hard-earned wisdom about trusting the process, accepting help, grieving what you lose, protecting your spark, saying no sooner, starting before you feel ready, surrounding yourself with the right people, and realizing that the path rarely unfolds the way you thought it would.
For any wantrepreneur or entrepreneur who feels behind, uncertain, afraid, or tempted to wait for perfect clarity, this episode is a reminder that you do not need the whole road mapped out. You need the courage to take the next step — and the willingness to keep becoming the person your journey is shaping you into.
✨ What You’ll Take Away
In this episode, you’ll learn how to:
Trust that your experiences are shaping you, even when they feel messy or disappointing.
Accept help, be vulnerable, and share your story more openly.
Stop forcing every opportunity to become “the one” and trust the direction your energy is taking you.
Make room for grief so you can continue loving, dreaming, and building.
Choose the right people to surround yourself with.
Say no earlier, think less, and move before everything feels perfect.
Come back to your “why” when fear, rejection, or uncertainty gets loud.
Stop waiting for the perfect moment to start the thing that has been on your heart.
Recognize that some people are wired to build — and that safety is not always the same as alignment.
🎙️ Meet the Collab Week Contributors
Lisa Larson — Mindful Corporate Mastery
Lisa Larson is the founder of Mindful Corporate Mastery, where she helps leaders and high performers build clarity under pressure before reactivity takes control. Her work focuses on performance-focused mindfulness, micro-interventions, and sustainable operating rhythms that support clearer thinking, better decisions, and long-term performance.
Connect with Lisa:
Website: https://www.mindfulcorporatemastery.com
LinkedIn: https://www.linkedin.com/in/lisa-larson-atx/
Free Program: https://awakeningperformance.com/5-day-clarity-challenge/
Spotify: https://open.spotify.com/show/6EqbbvCrXoBgtEt21ZItVX?si=fMY2efj0S7KTfwCikdibHg
Jane Alexander — Emma Advisor
Jane Alexander is the founder and CEO of Emma Advisor, an AI platform helping families navigate the path from high school to college with more clarity, strategy, and confidence. After an unconventional educational path and more than a decade advising leaders at over 200 colleges and universities, Jane built Emma Advisor from the belief that opportunity should not depend on insider knowledge, social capital, or expensive consultants.
Connect with Jane:
Website: https://emmaadvisor.ai/
Nate Hebbert — SelfWare Consulting
Nate Hebbert is an entrepreneur and software engineer who previously worked for 3M, KPMG, and Domo, where he developed custom Java code for Fortune 500 clients. After burnout threatened to derail his career, Nate became obsessed with helping tech companies beat burnout without pressing pause. Today, he is the founder and CEO of SelfWare Consulting.
Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting
Nicholas Cook — Money 101 Academy
Nicholas Cook is a blogger, teacher, real estate investor, and founder of Money 101 Academy. His background includes work as a financial advisor and paraplanner, teaching personal finance, English, literature, theology, investing, and algebra, and building online projects across writing, web design, YouTube, ecommerce, affiliate marketing, and email marketing.
Connect with Nicholas:
Website: https://money101academy.com/
LinkedIn: https://www.linkedin.com/in/nicholas-cook77/
Life, Business, and Creativity Blog: https://nickcook.blog
Mike Gross — Michael J. Gross LLC / Management System Certification Training Solutions
Mike Gross is a trainer, training provider, consultant, and auditor who helps organizations make sense of ISO standards and apply them in practical ways. With more than 35 years of experience, including growth into executive leadership roles, Mike focuses on helping organizations build understanding through training first, then refine and improve their systems. As a committed solopreneur, his approach is practical, straightforward, and centered on leaving people more capable than when he started.
Connect with Mike:
Website: https://mj-gross.com
LinkedIn: https://www.linkedin.com/in/mj-gross/
Company LinkedIn: https://www.linkedin.com/company/michael-j-gross-llc/
LinkedIn Showcase: https://www.linkedin.com/showcase/mscertts/
Leslie Hemedes — KeepSaiQ
Dr. Leslie Hemedes is a clinical psychologist, entrepreneur, and founder of KeepSaiQ, a family intelligence platform reimagining how families preserve memories, stories, and meaning across generations. Her work sits at the intersection of psychology, entrepreneurship, technology, and human connection, with a mission to help families preserve not just what happened, but why it mattered.
Connect with Leslie:
Company Website: https://keepsaiq.com/
KeepSaiQ LinkedIn: https://www.linkedin.com/company/keepsaiq/
Leslie LinkedIn: https://www.linkedin.com/in/leslie-hemedes-psy-d-b02b4022/
Shawn Sundsvold — GoldBear Media
Shawn Sundsvold is the co-founder and COO of GoldBear Media, a marketing agency based in Westminster, Maryland. After years of solving business problems across sales, operations, management, and marketing roles, Shawn joined his wife Kelly full-time in GoldBear Media to help small and medium-sized businesses improve their marketing, branding, online presence, social media, email marketing, and growth.
Connect with Shawn:
Website: https://goldbear.media/
Instagram: https://www.instagram.com/goldbear.media/
YouTube: https://www.youtube.com/@GoldBearMedia
Stephen Custer — Dry Humor Marketing
Stephen Custer started Dry Humor Marketing because he believes marketing is seriously fun. He helps clients combine strategy, data, video, photography, websites, and authentic storytelling so they can inspire people to act instead of simply throwing ideas against the wall to see what sticks.
Connect with Stephen:
Website: https://www.dryhumormarketing.com/
LinkedIn: https://www.linkedin.com/in/stephen-custer/
🚀 Action Steps For Wantrepreneurs and Entrepreneurs
Write a short voicemail or letter to your younger self. Notice what themes, regrets, or encouragements come up.
Ask where you are forcing a path instead of following the energy, signals, and opportunities already showing up.
Identify one area where you need to accept help instead of carrying everything alone.
Look at one disappointment or closed door and ask whether it might be redirection rather than rejection.
Choose one thing you have been waiting to start and take the smallest possible step this week.
Protect your spark by reconnecting with the deeper reason you wanted to build in the first place.
Surround yourself with one person, room, or community that reflects the kind of life and business you want to grow into.
Practice saying no to one thing that is not yours to carry.

In this special Collab Week episode of Wantrepreneur to Entrepreneur, nine founders answer one creative and surprisingly powerful question:
What is a concept from another discipline, hobby, or part of life that changed how you think as a founder?
You’ll hear from Shawn Sundsvold, Jaimz Hodge, Jane Alexander, Drew Dorenfest, Erik Berglund, Lisa Larson, Nate Hebbert, Stephen Custer, and Nicholas Cook as they pull lessons from recovery, fiction writing, gardening, baseball, fitness, running, software engineering, sketch comedy, poetry, and more.
The result is a wide-ranging episode about patience, systems, storytelling, recovery, consistency, craft, perspective, and the small lessons that quietly reshape how we build.
For any wantrepreneur or entrepreneur who feels like business wisdom only comes from business books, this episode is a reminder that some of the best founder lessons are hiding in plain sight — in the hobbies you love, the disciplines you practice, the challenges you survive, and the patterns you notice when you slow down enough to pay attention.
✨ What You’ll Take Away
In this episode, you’ll learn how to:
Use life’s highs and lows as perspective instead of letting them define you.
Move beyond passion by intentionally studying your craft.
Build a startup with the patience and care of a gardener.
Stop swinging for home runs and focus on getting on base consistently.
Treat your business like something that needs regular self-care.
Build recovery into your operating rhythm instead of glorifying exhaustion.
Apply systems thinking from software engineering to business problems.
Use storytelling to build trust in sales, marketing, and leadership.
See creative hobbies as training grounds for better communication and business growth.
🎙️ Meet the Collab Week Contributors
Shawn Sundsvold — GoldBear Media
Shawn Sundsvold is the co-founder and COO of GoldBear Media, a marketing agency based in Westminster, Maryland. After years of solving business problems across sales, operations, management, and marketing roles, Shawn joined his wife Kelly full-time in GoldBear Media to help small and medium-sized businesses improve their marketing, branding, online presence, social media, email marketing, and growth.
Connect with Shawn:
Website: https://goldbear.media/
Instagram: https://www.instagram.com/goldbear.media/
YouTube: https://www.youtube.com/@GoldBearMedia
Jaimz Hodge — Cart Catalyst
Jaimz Hodge helps ecommerce brands convert more customers by eliminating the invisible friction in their buying experience, from ad click to checkout. Through Cart Catalyst, he helps entrepreneurs get their products and ideas online, selling through Shopify and advertising through Google Ads.
Connect with Jaimz:
Website: https://www.cartcatalyst.com
Jane Alexander — Emma Advisor
Jane Alexander is the founder and CEO of Emma Advisor, an AI platform helping families navigate the path from high school to college with more clarity, strategy, and confidence. After an unconventional educational path and more than a decade advising leaders at over 200 colleges and universities, Jane built Emma Advisor from the belief that opportunity should not depend on insider knowledge, social capital, or expensive consultants.
Drew Dorenfest — Client Magnet CRM
Drew Dorenfest is a marketing expert who has worked with global brands including Netflix, Apple, Warner Bros., the NFL, and more as a video editor. Today, through Client Magnet CRM, he helps small business owners grow their brands through more clients, more 5-star reviews, stronger SEO, and more sales.
Connect with Drew:
Website: https://clientmagnetcrm.com
Erik Berglund — The Language of Leadership / Loominary
Erik Berglund is the founder of The Language of Leadership and Loominary, where he builds custom skill simulation systems that help teams practice the difficult conversations that drive performance.
Connect with Erik:
Website: https://www.languageofleadership.io
Website: https://www.loominary.io
LinkedIn: https://www.linkedin.com/in/emberglund/
Lisa Larson — Mindful Corporate Mastery
Lisa Larson is the founder of Mindful Corporate Mastery, where she helps leaders and high performers build clarity under pressure before reactivity takes control. Her work focuses on performance-focused mindfulness, micro-interventions, and sustainable operating rhythms that support clearer thinking, better decisions, and long-term performance.
Connect with Lisa:
Website: https://www.mindfulcorporatemastery.com
LinkedIn: https://www.linkedin.com/in/lisa-larson-atx/
Free Program: https://awakeningperformance.com/5-day-clarity-challenge/
Spotify: https://open.spotify.com/show/6EqbbvCrXoBgtEt21ZItVX?si=fMY2efj0S7KTfwCikdibHg
Nate Hebbert — SelfWare Consulting
Nate Hebbert is an entrepreneur and software engineer who previously worked for 3M, KPMG, and Domo, where he developed custom Java code for Fortune 500 clients. After burnout threatened to derail his career, Nate became obsessed with helping tech companies beat burnout without pressing pause. Today, he is the founder and CEO of SelfWare Consulting.
Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting
Stephen Custer — Dry Humor Marketing
Stephen Custer started Dry Humor Marketing because he believes marketing is seriously fun. He helps clients combine strategy, data, video, photography, websites, and authentic storytelling so they can inspire people to act instead of simply throwing ideas against the wall to see what sticks.
Connect with Stephen:
Website: https://www.dryhumormarketing.com/
LinkedIn: https://www.linkedin.com/in/stephen-custer/
Nicholas Cook — Money 101 Academy
Nicholas Cook is a blogger, teacher, real estate investor, and founder of Money 101 Academy. His background includes work as a financial advisor and paraplanner, teaching personal finance, English, literature, theology, investing, and algebra, and building online projects across writing, web design, YouTube, ecommerce, affiliate marketing, and email marketing.
Connect with Nicholas:
Website: https://money101academy.com/
LinkedIn: https://www.linkedin.com/in/nicholas-cook77/
Life, Business, and Creativity Blog: https://nickcook.blog
🚀 Action Steps For Wantrepreneurs and Entrepreneurs
Identify one hobby, discipline, or life experience that has already taught you something useful about business.
Pick one area of your business where you have relied on talent or instinct, then study someone who has mastered that craft.
Replace one “home run” goal with a smaller, repeatable action you can take consistently.
Block time on your calendar for business self-care: systems, team support, metrics, strategy, or reflection.
Build recovery into your week before your body or brain forces you to.
Look at one recurring business problem and break it down like a system: inputs, steps, decisions, outputs.
Turn one fact-heavy pitch, email, or piece of content into a story with a hook, journey, and takeaway.
Revisit a creative hobby and ask how it might sharpen your communication, leadership, or founder instincts.

In this special Collab Week episode of Wantrepreneur to Entrepreneur, four founders answer one powerful question:
What is an opportunity you almost ignored — but now realize changed everything?
You’ll hear from Jane Alexander of Emma Advisor, Shawn Sundsvold of GoldBear Media, Mike Gross of Michael J. Gross LLC and Management System Certification Training Solutions, and Nate Hebbert of SelfWare Consulting as they each share a moment they could have easily dismissed.
A bootcamp that felt intimidating.
A cold email that could have been deleted.
A coaching opportunity that seemed inconvenient.
A local resource that could have been overlooked.
Each story reveals the same lesson: some of the biggest entrepreneurial breakthroughs do not arrive looking obvious, polished, or perfectly timed. Sometimes they show up as discomfort, doubt, outreach, community, or an opportunity you do not yet feel ready for.
For any wantrepreneur or entrepreneur wondering whether to take the call, join the room, ask for help, invest in themselves, or say yes to the thing that scares them, this episode is a reminder to look twice. The opportunity that changes everything might already be sitting right in front of you.
✨ What You’ll Take Away
In this episode, you’ll learn how to:
Recognize opportunities even when they do not look like opportunities at first.
Bet on yourself when you feel underqualified, intimidated, or unsure.
Use new tools, AI, and accessible technology to move faster without waiting for permission.
Reframe cold outreach, local events, and free resources as potential doors instead of distractions.
Invest in personal growth before you feel “ready” to become the next version of yourself.
Build a stronger entrepreneurial support system so you do not have to figure everything out alone.
🎙️ Meet the Collab Week Contributors
Jane Alexander — Emma Advisor
Jane Alexander is the founder and CEO of Emma Advisor, an AI platform helping families navigate the path from high school to college with more clarity, strategy, and confidence. Her own path included homeschooling in rural Idaho, community college, transferring to a private university, graduate work at Harvard University, and more than a decade advising leaders at over 200 colleges and universities on enrollment, student success, and strategy. Emma Advisor grew from her belief that access to college strategy should not depend on money, insider knowledge, or social capital.
Connect with Jane:
Website: https://emmaadvisor.ai/
Shawn Sundsvold — GoldBear Media
Shawn Sundsvold is the co-founder and COO of GoldBear Media, a marketing agency based in Westminster, Maryland. After years of solving problems across business development, sales, marketing, operations, and management, Shawn joined his wife Kelly in building GoldBear Media full time. Today, they help small and medium-sized businesses improve their marketing, branding, online presence, social media, email marketing, and growth.
Connect with Shawn:
Website: https://goldbear.media/
Instagram: https://www.instagram.com/goldbear.media/
YouTube: https://www.youtube.com/@GoldBearMedia
Mike Gross — Michael J. Gross LLC / Management System Certification Training Solutions
Mike Gross is a trainer, training provider, consultant, and auditor who helps organizations make sense of ISO standards and apply them in practical ways. With more than 35 years of experience, including growth into executive leadership roles, Mike focuses on helping organizations build understanding through training first, then refine and improve their systems. As a committed solopreneur, his approach is practical, straightforward, and centered on leaving people more capable than when he started.
Connect with Mike:
Website: https://mj-gross.com
LinkedIn: https://www.linkedin.com/in/mj-gross/
Company LinkedIn: https://www.linkedin.com/company/michael-j-gross-llc/
LinkedIn Showcase: https://www.linkedin.com/showcase/mscertts/
Nate Hebbert — SelfWare Consulting
Nate Hebbert is an entrepreneur and software engineer who previously worked for 3M, KPMG, and Domo, where he developed custom Java code for Fortune 500 clients. After burnout threatened to derail his career, Nate became obsessed with solving one problem: how to escape the cycle of burnout. Today, he is the founder and CEO of SelfWare Consulting, helping tech companies beat burnout without pressing pause.
Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting
💡 The Opportunities They Almost Missed
Jane Alexander: The intimidating room that changed the trajectory of the company
Jane’s opportunity came through a bootcamp that felt outside her comfort zone. As a non-technical founder building an AI platform, it would have been easy to assume she did not belong in a room full of technical builders and Silicon Valley expertise. Instead, she said yes. That decision helped her learn new tools, build with more confidence, save significant money, and rethink what she was capable of creating herself.
Key reminder: Do not let your current skill set define the limits of your vision.
Mike Gross: The cold email that became a hidden door
Mike’s opportunity arrived in the form many entrepreneurs are trained to ignore: cold outreach. But instead of immediately dismissing it, he paid attention to the way the opportunity showed up — professional, persistent, respectful, and not overly demanding. A simple exploratory conversation opened the door to a global business opportunity that expanded what he thought was possible.
Key reminder: You do not have to say yes to every opportunity, but you should learn how to recognize signal through the noise.
Shawn Sundsvold: The coaching opportunity that expanded his vision
For Shawn, the opportunity was not a tool, lead, or sales call. It was personal development. At a time when he was still trying to figure out what business ownership could look like, coaching helped him see a different future for himself. It challenged how he thought about life, work, possibility, and what he was capable of building.
Key reminder: Sometimes the opportunity is not about the business yet — it is about becoming the person who can build it.
Nate Hebbert: The local resource that became a community
Nate’s story is a reminder that entrepreneurship does not have to be as lonely as it often feels. By exploring local business resources, libraries, councils, and community networks, he found support, connection, and momentum. One small step into a local ecosystem created a ripple effect of relationships and opportunities.
Key reminder: The support you need may already exist closer than you think.
🚀 Action Steps For Wantrepreneurs and Entrepreneurs
Look back at one opportunity you recently dismissed and ask whether it deserves a second look.
Say yes to one room, event, call, or learning opportunity that feels slightly intimidating but potentially expansive.
Take one low-risk exploratory call before deciding whether an unfamiliar opportunity is worth pursuing.
Search for local business resources in your city, region, library system, chamber, or industry community.
Invest in one personal development opportunity that challenges how you currently see your future.
Identify one AI, no-code, or automation tool that could help you build something you previously assumed you had to outsource.

In this special Collab Week episode of Wantrepreneur to Entrepreneur, five founders answer one deceptively powerful prompt:
What is the single most important question you ask yourself to stay focused, make better decisions, and keep building?
You’ll hear from Brent Newton of myOwl, Mary Gunther of The Social G Co., Nate Hebbert of SelfWare Consulting, Stephen Custer of Dry Humor Marketing, and Shawn Sundsvold of GoldBear Media as they each reveal the internal question that helps guide their work, energy, leadership, and growth.
From asking whether something is truly CEO-level work, to buying back time, to protecting your energy, to shifting from “why?” to “why not?”, this episode is a masterclass in the questions that shape better entrepreneurs.
For any wantrepreneur or entrepreneur feeling stretched, distracted, overwhelmed, or unsure where to focus next, this episode will help you rethink the conversations you’re having with yourself — because the quality of your questions often determines the quality of your next move.
✨ What You’ll Take Away
In this episode, you’ll learn how to use better questions to:
Filter your to-do list down to the work that actually moves the business forward.
Identify what can be delegated, automated, or eliminated so you can buy back your time.
Reframe doubt and hesitation into possibility and action.
Protect your energy as a real business asset, not a luxury.
Clarify your highest priority by factoring in urgency, growth, and personal capacity.
Recognize and nurture the entrepreneurial spirit in yourself and others.
🎙️ Meet the Collab Week Contributors
Brent Newton — myOwl
Brent is the co-founder and CEO of myOwl, an AI-powered platform helping student athletes and their families take back control of their time. Built around the “Play Hard, Study Smart System™,” myOwl combines homework aggregation, sports schedule syncing, and AI-generated study plans into one unified calendar. Brent built the company alongside his daughter after living the student-athlete time crunch firsthand.
Connect with Brent:
Website: https://www.getmyowl.com
LinkedIn: https://www.linkedin.com/in/brent-newton-myowl
Mary Gunther — The Social G Co.
Mary Gunther is the founder of The Social G Co., a Grand Rapids-based social media agency helping brands build strategic, authentic, impossible-to-ignore social presences. With a background in organizational development, HR, operations, community-building, and brand strategy, Mary brings a sharp mix of creativity and business growth to the companies she serves.
Connect with Mary:
Website: https://www.thesocialgco.com
Instagram: https://www.instagram.com/thesocialgco/
LinkedIn: https://www.linkedin.com/in/marykgunther/
Nate Hebbert — SelfWare Consulting
Nate Hebbert is an entrepreneur and software engineer who previously worked for 3M, KPMG, and Domo, where he developed custom Java code for Fortune 500 clients. After burnout threatened to derail his career, Nate became obsessed with helping tech companies beat burnout without pressing pause. Today, he is the founder and CEO of SelfWare Consulting.
Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting
Stephen Custer — Dry Humor Marketing
Stephen started Dry Humor Marketing because he believes marketing is seriously fun. He helps clients combine strategy, data, and authentic storytelling so they can inspire people to act instead of simply throwing ideas against the wall to see what sticks.
Connect with Stephen:
Website: https://www.dryhumormarketing.com/
LinkedIn: https://www.linkedin.com/in/stephen-custer/
Shawn Sundsvold — GoldBear Media
Shawn Sundsvold is the co-founder and COO of GoldBear Media, a marketing agency based in Westminster, Maryland. After years of solving business problems across sales, operations, management, and marketing roles, Shawn joined his wife Kelly full-time in GoldBear Media to help small and medium-sized businesses improve their marketing, branding, online presence, social media, email marketing, and growth.
Connect with Shawn:
Website: https://goldbear.media/
Instagram: https://www.instagram.com/goldbear.media/
YouTube: https://www.youtube.com/@GoldBearMedia
💡 The Questions That Shape Better Founders
Mary Gunther: “Is this CEO-level work?”
Mary’s question is a direct challenge to every entrepreneur who confuses motion with momentum. Not every task deserves the founder’s time, energy, or attention. If the business is going to grow, the leader has to grow too — and that means protecting the calendar, saying no more often, and focusing on the work only the CEO can do.
Key reminder: Busy is not the same as building.
Shawn Sundsvold: “Where can I buy back my time?”
Shawn’s question reframes time as something entrepreneurs can intentionally reclaim. Instead of assuming every task belongs on your plate, ask what can be delegated, automated, systemized, or handed off. The time you buy back becomes the space you use to lead your team, grow the business, and be present in the rest of your life.
Key reminder: You do not have to do everything yourself.
Brent Newton: “Why did it take me so long?”
Brent’s reflection is both personal and generational. As a first-time founder building myOwl alongside his daughter, he reminds us that entrepreneurship can start at any age — but when we see that spark in someone younger, we should nurture it. Sometimes the most important question is not just how we build, but how we help others believe they can build too.
Key reminder: It is never too late to start, and never too early to encourage someone else.
Stephen Custer: “Why not?”
Stephen’s question is simple, but powerful. Many founders default to asking “why?” from a place of fear, scarcity, or pessimism. But adding one small word — “not” — changes the energy of the entire question. “Why not?” opens the door to possibility, experimentation, hiring, scaling, and trying the thing you might otherwise talk yourself out of.
Key reminder: Sometimes your next breakthrough starts with a better question.
Nate Hebbert: “What is my highest priority right now?”
Nate’s question goes deeper than urgency. Your highest priority is not always the loudest task, the nearest deadline, or the thing someone else wants from you. It also includes your growth, your energy, and your ability to do quality work. For entrepreneurs especially, protecting your physical, mental, and emotional capacity is not separate from business performance — it fuels it.
Key reminder: Your energy is part of your operating system.

In this first-ever Collab Week episode of Wantrepreneur to Entrepreneur, four past guests come together to answer one powerful question:
What’s a tiny decision you made that changed everything?
You’ll hear from Stephen Custer of Dry Humor Marketing, Nate Hebbert of SelfWare Consulting, Drew Dorenfest of Client Magnet CRM, and Janice Kephart of ZipID as they each share a seemingly small moment that created a major ripple effect in their entrepreneurial journey.
From writing down a goal, to helping a friend for free, to saying yes to a terrifying opportunity, to using a job as a training ground for future business ownership, this episode is a reminder that transformation rarely starts with a grand master plan. More often, it starts with one small, decisive action.
For any wantrepreneur or entrepreneur feeling stuck, this episode offers real-world proof that the next move doesn’t have to be massive. It just has to be intentional.
✨ What You’ll Take Away
In this episode, you’ll hear how small decisions can become major turning points, including:
Why writing down your goals can help shape your identity and future direction.
How one free project can become the proof of concept that launches a business.
Why scary opportunities often become the moments that create credibility and confidence.
How your current job can become a paid training ground for your future company.
Why you don’t need perfect clarity to begin — you just need one committed step.
How tiny moments of courage, service, and curiosity can compound into major entrepreneurial momentum.
🎙️ Meet the Collab Week Contributors
Stephen Custer — Dry Humor Marketing
Stephen started Dry Humor Marketing because he believes marketing is seriously fun. He helps clients combine strategy, data, and authentic storytelling so they can inspire people to act instead of simply throwing ideas against the wall to see what sticks.
Connect with Stephen:
Website: https://www.dryhumormarketing.com/
LinkedIn: https://www.linkedin.com/in/stephen-custer/
Nate Hebbert — SelfWare Consulting
Nate Hebbert is an entrepreneur and software engineer who previously worked for 3M, KPMG, and Domo, where he developed custom Java code for Fortune 500 clients. After experiencing burnout firsthand, he became obsessed with helping tech companies beat burnout without pressing pause. Today, he is the founder and CEO of SelfWare Consulting.
Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting
Drew Dorenfest — Client Magnet CRM
Drew Dorenfest is a marketing expert who has worked with global brands including Netflix, Apple, Warner Bros., the NFL, and more as a video editor. Today, through Client Magnet CRM, he helps small business owners grow their brands through more clients, more 5-star reviews, and more sales.
Connect with Drew:
Website: https://clientmagnetcrm.com
Janice Kephart — ZipID
Janice Kephart is the founder of ZipID and brings decades of experience at the intersection of law, policy, national security, identity verification, and biometric technology. Her work has included drafting the federal identity theft criminal statute, serving with the 9/11 Commission, contributing to REAL ID and biometric border entry-exit systems, and now building technology to bring greater trust and integrity to identity verification.
Connect with Janice:
Website: https://www.zipidapp.com
LinkedIn: https://www.linkedin.com/in/janicekephart/
💡 Key Lessons From This Episode
Define who you’re becoming.
Nate’s story shows the power of writing down your goals and allowing that act to shape your identity, attention, and future decisions.
Create proof before you chase perfection.
Drew’s story is a reminder that helping one person, even for free, can become the case study that gives you confidence and opens the door to paying clients.
Say yes before you feel ready.
Janice’s story reveals how one intimidating opportunity can become the moment that changes how you see yourself and how the world sees your expertise.
Use where you are to build where you’re going.
Stephen’s story shows how your current job, role, or environment can become the place where you develop the exact skills you’ll later use to build your own business.
🧠 Memorable Moments
“Your environment and the experiences that you've had in the past do affect who you are right now, but the future in so many ways is for you to decide.” — Nate Hebbert
“That small decision just to help a friend and try something changed everything for me.” — Drew Dorenfest
“It gave me the confidence that I had something to offer in a way that I never had it before.” — Janice Kephart
“I learned how to make videos that engaged people and educated them and most importantly caused them to act.” — Stephen Custer
🚀 Action Steps For Wantrepreneurs and Entrepreneurs
Write down one goal you want to grow into and keep it somewhere you’ll see it often.
Find one person or business you can help this week to create real-world proof of your skills.
Say yes to one opportunity that scares you but could stretch your credibility.
Look at your current job, project, or environment and ask: “What skill can I develop here that my future business will need?”
Stop waiting for the huge breakthrough and identify the tiny decision you can make today.