Category: Leadership

Job Searching as an Entrepreneur: Why You Don't Need to Go It Alone

Job Searching as an Entrepreneur: Why You Don’t Need Go It Alone

You were prepared for change.

You knew this next chapter wouldn’t be easy.

But nothing quite prepares you for job searching when you’re an entrepreneur.

You thought your biggest challenge would be updating your résumé.

Instead, it’s the quiet, grinding uncertainty that no one warned you about.

The job search isn’t just a search. It’s a test of resilience.

You apply for roles that sound like a fit. You try to explain what you did as a founder without sounding like you’re overqualified – or worse, like you’re starting over after what the interviewer may assume as a failure.

You wonder if the recruiter on the other side understands what it meant to build a brand from nothing, lead a team, manage budgets, grow revenue, solve crises.

You wonder if they can see the value behind the title of “Founder.”

You hit submit and wait. And wait. And wait.

Sometimes there’s a rejection. More often, just silence.

You start to question your instincts.

You rewrite your story. Again.

You try to stay upbeat for the next interview, even as your confidence thins.

And you begin to ask: Is it just me? Am I doing this wrong?

It’s not just you. And you’re not doing it wrong.

Job searching as an entrepreneur is uniquely challenging.

Not because you lack skills, but because traditional hiring systems aren’t built to understand non-traditional paths.

But here’s what no one tells you: You don’t need to muscle through this alone.

You don’t have to.

The missing piece in your job search might not be a better resume or a new strategy.

It might be a support circle, a space where you’re reminded of what you bring to the table, even when the world feels unsure of where to seat you.

What can support circles do for you?

A strong circle doesn’t just offer encouragement. It changes the experience of job searching as an entrepreneur in real, tangible ways.

First, you gain clarity. Talking with others helps you see yourself and your transferable skills more clearly.

You also learn how to tell your story. A support group helps you shape your founder journey into a compelling narrative that hiring managers can understand.

You get unstuck. Whether it’s a new connection, a practical tip, or just someone who’s been there, the right support gives you momentum.

Lastly, you feel human again. Being around others who get it helps you shake off the isolation, the imposter syndrome, and maybe even the shame that job searching can trigger.

You’ve carried enough alone. It’s time to let someone help you.

Finding the right support is what Job Searching for Entrepreneurs is all about. It’s not another job-searching, resume-writing workshop.

It’s a gathering place for people who are in the thick of the search, who’ve been refreshing job boards, second-guessing themselves, and wondering what’s next.

It’s a chance to talk about what really makes a difference: connection, community, and support that actually understands where you’re coming from.

In the upcoming session of this conversation, titled “Finding Support as a Job-Searching Entrepreneur,” we’ll explore:

What makes the job search uniquely hard for founders
How to find the right people to walk this path with you
Where to look for mentorship, guidance, and belonging
How to ask for help in a way that feels empowering

This session is on August 19, 2025, at Offbeat Coffee in Salem, OR, co-facilitated by Conrad Rohleder of Clearinity and Malee Ojua of Sacred Fire Creative.

The job search is hard.

But you don’t have to do it alone.

And you were never meant to.

Join us for this part of Job Searching for Entrepreneurs.

Let this be the session that reminds you that you’re not stuck.

You’re evolving. And there are people who see what you bring, even when the hiring algorithm doesn’t.

Joining is free. RSVP today.

Oregon Startup Conference 2025: Building Strong Roots for the Future of Community

At the Oregon Startup Conference, held June 20, 2025, we witnessed something rare.

It wasn’t just a gathering of entrepreneurs. It was a moment—a shared breath—where hope, vulnerability, and possibility met in the same room.

Founders came with big dreams and unfinished ideas.

Mentors came with open hands and honest words.

Strangers became collaborators. Ideas became momentum.

And what started as a conference became something much deeper: community.

One quote echoed through our hearts all day long:

“Even if I knew that tomorrow the world would go into pieces, I would still plant my apple tree.” — Martin Luther King Jr.

That spirit was everywhere. In every pitch, every breakout session, every side conversation over coffee. People chose to plant something—an idea, a connection, a belief that what they’re building matters.

We created space for people to show up as they are. No polish required. Just passion, persistence, and purpose.

And that’s what made this event unforgettable.

Because at the heart of every startup is a voice. A story. A reason for doing the hard thing anyway.

At Sacred Fire Creative, that’s what we’re here to nurture: the voice that connects, the story that resonates, the brand that builds bridges between humans.

🧡 If you’re ready to find your authentic voice and use it to spark connection in your community, we’d love to collaborate.

How to Ace the Job Interview as an Entrepreneur

For years, your job interview was a client pitch.

You didn’t talk about your job qualifications. Instead, you showed them.

You didn’t wait to be hired to show what you can do. Instead, you built a business around what you can do.

You wore every hat, made every decision, and held the full weight of success (and failure) on your shoulders.

But now, something has shifted.

Maybe you’re craving stability. Maybe you’re burned out. Or maybe, for the first time in a long time, you’re curious about what it might feel like to be part of a team again – this time, not as the leader, but as a contributor with clear boundaries, shared goals, and room to breathe.

And that’s brought you here: preparing to reenter the world of traditional employment.

But let’s be honest. Job interviews hit differently when you’ve been the boss.

In the first part of this blog series, we talked about the resume and the cover letter. Here, we’re going to tackle the job interview.

Why Interviews Are Uniquely Challenging for Entrepreneurs

When you’re used to creating your own opportunities, sitting across from someone evaluating your qualifications can make you feel vulnerable, even strange.

There’s a quiet fear underneath.

Will they understand my story? Will they think I failed?

Am I too much? Or not enough?

These are common and completely normal questions for entrepreneurs making this leap.

Here’s why the interview stage can feel especially hard:

Your career path is nonlinear. Traditional roles follow a ladder. Yours was more like a jungle gym.
You’re afraid they’ll think you can’t follow. You’re no longer the CEO, but that doesn’t mean you can’t thrive in a supportive role. Still, that transition can be hard to communicate.

What Hiring Managers Need to Hear

You bring incredible value to the table. But it’s up to you to make that visible.

Here’s how to make your experience resonate in the interview:

Reframe your story.

Don’t just say, “I ran a business.” Translate it.

I launched and scaled a client-focused brand, led a team of five, managed a $100K budget, and built a marketing system that generated consistent leads through organic social media.

Be specific with your story and focus on outcomes. Connect your experience to the job you’re applying for.

Address the elephant in the room.

If your business closed or paused, acknowledge it confidently.

After several meaningful years in entrepreneurship, I’m choosing this next chapter intentionally. I’m excited to contribute in a focused role where I can apply my experience and collaborate with a team.

Most employers aren’t put off by your business pausing, closing, or being set aside. They just want to understand your “why” and know you’re ready to show up fully.

Shift the narrative from “boss” to “team player.”

One of the biggest assumptions you may face is that you won’t take direction or adapt well to the hierarchy.

Prove them wrong by sharing examples of collaborative partnerships, taking client feedback, and learning from mentors or peer networks.

Let them see your willingness to grow within a team, without needing to lead everything.

Use the STAR Method to Tell Compelling Stories

Entrepreneurs are natural storytellers. But job interviews require a more structured kind of storytelling.

That’s where the STAR method comes in.

STAR stands for:

Situation: What was going on?
Task: What challenge or goal were you facing?
Action: What specific steps did you take?
Result: What was the outcome?

This method helps you clearly demonstrate your value through real-life experiences. And that’s something entrepreneurs have in abundance.

Let’s break it down:

SITUATION: Set the Scene.

“Our customer retention rates were dropping, and we realized our onboarding process wasn’t setting clients up for success.”

TASK: Define the Challenge or Goal.

“I need to redesign the onboarding system to improve retention and create a more seamless client experience.”

ACTION: Describe What You Did.

“I mapped out the existing process, created a new step-by-step welcome journey, and trained my team on delivering it consistently.”

RESULT: Share the Outcome.

“Client retention improved by 35% over the next six months, and support tickets dropped by half.”

Here are a few STAR tips that entrepreneurs can use during the job interview:

Choose diverse stories. Highlight collaborations, problem-solving, and resilience, not just your wins.
Tailor your examples. Connect them directly to the skills the job requires.
Practice out loud. STAR stories are designed to be spoken so they can be remembered.
Stay focused. The structure helps you avoid rambling, a common habit among founders.

Using the STAR method turns your entrepreneurial experience into concise, impressive stories that resonate with hiring managers. It shows that you’re not just experienced; you’re self-aware, coachable, and ready to contribute.

Find the Right Support

Transitioning from entrepreneurship to traditional employment doesn’t just involve a career shift. It’s diving into an identity shift.

And it’s okay to need help navigating it.

That’s why we’re hosting the second session in our Job Searching for Entrepreneurs series: Nailing the Interview: How to Tell Your Story with Confidence.

Whether you’re getting ready for your first interview in years or struggling to translate your founder journey into corporate language, this event is for you. We’ll walk through real examples and hold space for the complexity of this transition without judgment.

This second session is on August 12, 2025, at Offbeat Coffee in Salem, OR. Just like the first session, it will be led by Conrad Rohleder of Clearinity and Malee Ojua of Sacred Fire Creative.

Come as you are – curious, cautious, or completely overwhelmed. You’ll leave with tools, language, and renewed clarity for your next step.

Because you’re not starting over.

You’re starting fresh, with experience, perspective, and something powerful to offer.

RSVP here.

Scaling with Integrity: How Kristy Runge Helped Build HelloCare’s Operational Backbone

Kristy Runge didn’t just co-found a caregiving company. She architected its operational success.

With decades of experience in healthcare and business leadership, Kristy understood that meaningful care doesn’t scale on goodwill alone. It takes rigorous systems, thoughtful hiring, quality assurance, and leadership that balances compassion with performance.

That’s the foundation she helped build at HelloCare, a company now serving families in multiple cities across Oregon.

The System Behind the Soul

While HelloCare is known for its deeply personal, people-first approach to in-home care, much of that consistency comes from the operational design that Kristy helped create.

She implemented systems and processes at HelloCare that ensure quality at scale without sacrificing heart. Her leadership bridges the emotional weight of caregiving with the accountability and structure required to grow a service-based business that can last.

It’s that rare balance between heart and logistics that has made HelloCare not just sustainable but replicable.

Why Founders Should Hear Her Speak at the Oregon Startup Conference

Kristy Runge will be featured on the Success Panel at the Oregon Startup Conference on June 20, 2025, at George Fox University.

There, she will offer founders a transparent look into what it really takes to scale a mission-driven operation.

She’ll speak to the practical aspects that many early-stage businesses overlook: operational workflows, systems thinking, hiring for values and competence, and building processes that grow with your team – not against them.

If you’re an entrepreneur building in the service space, Kristy’s insights are both inspiring and actionable. She’s walked the road of taking a community-centered idea and turning it into a business with backbone. And she’s ready to share how.

Hear from founders like Kristy Runge, who know how to build for both heart and scale.

Slumberkins, Callie Christensen, Kelly Oriard

Slumberkins: How Two Moms Built a Global Brand for Early Learning and Emotional Wellness

In the heart of the Pacific Northwest, two lifelong friends transformed a shared passion for child development into a thriving business.

Kelly Oriard and Callie Christensen, co-founders of Slumberkins, have created a brand that not only comforts children but also empowers them with emotional intelligence.

Their journey from educators to entrepreneurs exemplifies the innovative spirit that defines the local startup ecosystem.

The Genesis of Slumberkins

Kelly and Callie are, first and foremost, friends. It was a friendship that began in childhood. Their paths eventually diverged: Kelly became a school counselor and family therapist in Portland, OR, while Callie built a career as a special education teacher in Vancouver, WA.

However, a mutual recognition of the lack of engaging emotional learning tools for children brought them back together. They began crafting stories and sewing plush creatures that embodied therapeutic concepts in 2015, thus laying the foundation for Slumberkins. Their initial creations, Bigfoot and Sloth, addressed self-esteem and relaxation. These characters resonated with parents and children alike.

In 2017, Kelly and Callie took their concept to Shark Tank. While they were not able to secure an investment, they pushed forward. That decision led to the development of a comprehensive product line that includes plushies, books, educational resources, and an Emmy-nominated television series produced by The Jim Henson Company. Slumberkins has since become a trusted resource for over 1.5 million families, offering tools that foster resilience and emotional growth in children.

In 2022, they brought in a CEO to focus on the business side of things at Slumberkins. Kelly transitioned into the Chief Therapeutic Officer, while Callie became the Chief Brand Officer.

Impact on the Oregon Startup Community

Beyond their business success, Kelly and Callie are active contributors to the local entrepreneurial landscape. They have shared their insights at events like the Bend Venture Conference, Portland Startup Week, and Starve Ups, providing guidance on fundraising and brand development.

Their efforts have not gone unnoticed. In 2022, they received the Entrepreneurial Achievement Award from the Oregon Entrepreneurs Network, recognizing their significant contributions to the state’s innovation economy. Their inclusion in Inc.’s 2023 Female Founders 200 List further underscores their influence and dedication to fostering a supportive environment for women in business.

Meet Kelly and Callie at the Oregon Startup Conference

Kelly and Callie’s journey embodies the essence of entrepreneurial success: identifying a need, creating a solution, and scaling it with authenticity and purpose. Their experience in building a mission-driven brand that prioritizes emotional wellness offers invaluable lessons for startups aiming to make a meaningful impact.

Their presence on the Success Panel at the Oregon Startup Conference will provide attendees with practical strategies and inspiration drawn from real-world experience.

Don’t miss the opportunity to engage with Kelly Oriard and Callie Christensen at the conference on June 20, 2025, at George Fox University. Their story is a testament to the power of combining passion with purpose, and their insights could be the catalyst for your own entrepreneurial journey.

Tech that Heals, Leadership that Elevates: How Rachel Dreilinger Is Bridging Innovation and Inclusion in MedTech

When Rachel Dreilinger co-founded NeuraMedica, she wasn’t just setting out to solve a surgical problem. She was aiming to change the way innovation works for patients, providers, and underrepresented entrepreneurs like herself.

A biomedical engineer by training and a systems thinker by instinct, Rachel brings over two decades of experience in medical development to her role as NeuraMedica’s CEO. Her path has taken her from engineering labs to executive leadership, but the heart of her work has always remained the same.

And that is to use technology to make people’s lives better.

A Simple Idea with Profound Impact

At the center of NeuraMedica’s story is DuraFuse™, an elegantly engineered bioabsorbable clip that offers a safer, faster alternative to traditional sutures for closing the dura mater during spinal surgery.

Designed to reduce the risk of cerebrospinal fluid leaks that come with traditional spinal surgery and improve surgical efficiency, DuraFuse is FDA-cleared and commercially viable. It’s a milestone that only a handful of startups in this corner of the medical space ever reach.

The journey to get there wasn’t simple.

Rachel and her co-founder, neurosurgeon Dr. Neil Roundy, began with a prototype and a bold idea. Backed by grants and early collaborations with Oregon Health & Science University, they methodically advanced their technology through years of clinical research, testing, and refinement.

Leading with Vision and Roots

Rachel is a proud member of the Diné (Navajo) Nation and one of the few Native American women leading a medical technology company. That perspective shapes everything she does, from how she leads her team to how she shows up for the broader community.

She’s a vocal advocate for inclusion in entrepreneurship and STEM, especially for women and Indigenous founders. Her leadership is visible not only inside NeuraMedica but also across Oregon’s startup ecosystem. Rachel frequently participates in regional pitch events, panels, and mentorship programs, where she offers real-world guidance to founders navigating similar hurdles.

Rachel has been recognized for that work, too. NeuraMedica was a finalist for Oregon Entrepreneurs Network’s Angel Oregon Life & Bioscience Investment in 2024. This is a clear sign that the innovation coming out of Mid-Willamette Valley is gaining significant attention.

Meet Rachel at the Oregon Startup Conference

On June 20, 2025, Rachel will be part of the Success Panel of the Oregon Startup Conference at George Fox University.

She does more than represent the future of MedTech. She’s helping to shape it. Her story is a reminder that great startups aren’t only built on good ideas. They’re built on perseverance, collaboration, and a vision that extends beyond the bottom line.

Don’t miss the opportunity to connect with Rachel Dreilinger. She’s someone worth knowing, whether you’re passionate about healthcare innovation, inclusive entrepreneurship, or just want to meet someone who is changing the game in their field.

Code, Defense, and Vision: How Tracy Camp of UpSight Is Changing the Cybersecurity Playbook

Most people only think about cybersecurity after something goes wrong.

But for Tracy Camp, the question has always been: “What if we could see the attack coming before it starts?

That question didn’t come out of nowhere. Tracy spent nearly two decades in the trenches of cybersecurity. He helped various organizations, from scrappy startups to Fortune 100 companies, fight back against evolving digital threats.

He’s worked with some of the biggest names in the field, including Carbon Black and McAfee. He’s seen ransomware change lives, shut down hospitals, and cost companies everything.

He knew we needed a new approach. So he built one.

From Pattern Recognition to Prediction

As co-founder and Chief Product Officer of UpSight Security, Tracy is leading a bold new chapter in the fight against cybercrime. It’s a fight that’s powered by AI, driven by data, and rooted in the idea that security should be proactive, not reactive.

At the heart of UpSight is a groundbreaking platform that does more than detect threats; it anticipates them.

Using techniques inspired by natural language processing (NLP), UpSight’s technology “reads” attacker behavior the way a human might read a book. It learns the patterns, understands the structure, and identifies the next likely move. It helps teams predict, interdict, and evict threats before they can do damage.

It’s like giving security teams a forward-moving time machine, and it’s working.

Building in Oregon, for Oregon

But Tracy isn’t just building a company. He’s helping build a community.

After winning third place in the 2023 Westside Pitch Competition, UpSight Security went on to secure funding from the Oregon Venture Fund. It’s an achievement that positioned the company as one of the region’s most promising up-and-comers in the cybersecurity space.

More than that, Tracy and his co-founders made a conscious choice to house their nationwide operations in Mid-Willamette Valley, where about half of the UpSight team is located. He’s deeply committed to growing Oregon’s tech ecosystem by taking on paid interns from Oregon State University through MECOP.

Through mentorship, advocacy, and collaboration, he’s creating opportunities for other founders to thrive right here at home.

Meet Tracy at the Oregon Startup Conference

At the Oregon Startup Conference, happening on June 20, 2025, at George Fox University, Tracy will join the Success Panel to talk about what it really takes to build and protect a startup in today’s high-stakes digital world.

His insights go beyond firewalls and code. He’ll speak to the mindset, the mission, and the million tiny decisions that separate survival from success.

Because in cybersecurity, as in entrepreneurship, the winners aren’t always the biggest. They’re the ones who can see what’s coming and act upon it before it’s too late.

Learn how to stay two steps ahead, whether you’re building a company, a product, or a secure future. Meet Tracy Camp at the Oregon Startup Conference and walk away with insight and inspiration.

From Engineer to Ecosystem Builder: How Rita Hansen Is Driving Climate Innovation in Oregon

Rita Hansen does more than build companies. She helps build a future where clean technology is the norm, not the exception.

With decades of experience in engineering, operations, and leadership, Rita has made a name for herself as a thoughtful, data-driven changemaker in the energy space.

Her career spans major industries, but her most defining work came as the co-founder and former CEO of Onboard Dynamics, a climate-tech startup that’s helping reshape how we reduce greenhouse gas emissions.

Turning an Idea into Impact at Onboard Dynamics

Onboard Dynamics began as a university research project at Oregon State University – Cascades back in 2013. Under Rita’s leadership, it grew into a nationally recognized innovator in methane emissions reduction.

She guided the company into developing technologies like the GoVAC® and GoFLO®. They are portable, self-powered compression systems that help utilities and fleet operators capture and reuse natural gas that would otherwise be wasted.

These systems do more than save money. They dramatically lower environmental impact, aligning both climate goals and operational needs.

With her steady hand at the helm, Onboard Dynamics secured federal grants, expanded commercial partnerships, and brought critical clean-energy technology into real-world use.

Mentorship, Advocacy, and Ecosystem Support

After transitioning out of her CEO role, Rita didn’t step away from innovation. Instead, she stepped deeper into community impact.

Today, she serves as a mentor with the OSU Advantage Accelerator and actively supports Oregon’s entrepreneurial ecosystem. Rita brings the same level of care and insight that fueled her own journey, whether she’s advising a new founder on market strategy or helping a startup secure non-dilutive funding.

She’s also a champion for diversity in STEM and cleantech. Rita advocates for inclusive innovation, especially for women and underrepresented founders working at the intersection of science, sustainability, and entrepreneurship.

A Trusted Voice in Clean Energy and Startup Growth

Rita’s influence has earned her national and international recognition. She represented the US at the Global Entrepreneurship Summit in 2017 and 2019. She also received the GRIT Award from ALLY Energy, which honors resilience and impact in the energy industry, in 2022.

But her focus remains local. She continues to invest her time, expertise, and energy into strengthening Oregon’s clean-tech pipeline, thus supporting the people and ideas that will shape a more sustainable tomorrow.

Connect with Rita at the Oregon Startup Conference

Rita Hansen will join the Success Panel at the Oregon Startup Conference this June 20, 2025, at George Fox University. Her story is one of steady leadership, purposeful innovation, and a deep commitment to building communities.

If you’re looking for inspiration or a blueprint for scaling with impact, you won’t want to miss the chance to hear from Rita.

Register for the Oregon Startup Conference. Meet founders like Rita Hansen and see what’s possible when vision meets execution.

Newberg’s Real Estate Powerhouse: Tina Smith’s Journey of Empowerment and Community Impact

When Tina Smith purchased her first home in 1998, she did more than cross a milestone. She discovered her calling.

What began as a personal investment quickly grew into a full-fledged passion for real estate. Over the years, she transitioned from homeowner to investor, flipper, landlord, and eventually a trusted real estate broker in the Portland metro area.

Strategic Mindset, Heart-Centered Service

Armed with an MBA and related certifications, Tina blends business acumen with a personal touch.

Her background in finance and project management allows her to approach real estate transactions with a sharp eye for detail and strategy. But what truly sets her apart is her unwavering commitment to the people she works with.

Tina does more than close deals. She builds relationships that last, offering support long after the paperwork is signed.

A Broker Building Community

Tina’s definition of success goes beyond profit margins. Deeply rooted in Newberg, she believes in giving back to the community that shaped her.

Tina’s work is guided by a spirit of service, whether she’s mentoring new homeowners, investing in neighborhood revitalization, or supporting local initiatives. She plays an active role in her community, driven by her genuine love for helping people, not just with finding a home.

Meet Tina at the Oregon Startup Conference

Tina Smith brings a grounded, real-world perspective to the Oregon Startup Conference on June 20, 2025, at George Fox University as a Startup Champion.

She has been actively supporting regional entrepreneurial initiatives, especially through her participation in Newberg’s Coffee Club for Startups.

As someone who has built her career from ground up, she understands the entrepreneurial grind. Her experience navigating risk, negotiating deals, and managing growth makes her insights especially valuable for startups exploring real estate, local investment, or sustainable business practices.

Stop by Tina’s table at the Conference. Whether you’re seeking entrepreneurial insight or simply an inspiring conversation about building a values-driven business, Tina is someone you’ll want in your network.

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