In this episode of Fiscally Awesome, Hiline CEO Matt Gardner explores the art and science of strategic business pivots with a legal influencer, sales leader, and now CRO at Latitude, Alex Su.

From shifting professional identities to recognizing when your business model needs a refresh, this conversation digs into how successful leaders know when it's time to change direction—and how to do it without losing momentum.

Discover:

1. Why professionals trained to avoid risk often struggle to embrace necessary pivots
2. How to recognize when "the cheese has moved" in your industry before your competitors do
3. Practical strategies for balancing caution with the need for speed in business decisions
4. Why understanding your true audience is crucial when shifting direction
5. The financial implications of pivoting too late (or too early)

Whether you're a founder at a crossroads, a professional considering a career shift, or a small business leader watching market dynamics change, this episode delivers candid insights about making smart pivots that create lasting competitive advantage.

No jargon, no fluff—just straight talk about how to stay fiscally awesome when everything around you is changing.

Tune in and learn how to turn market disruption into your next opportunity!

About Fiscally Awesome
Want to unfu*k your finances? Fiscally Awesome is produced by Hiline, where we make small business finances stress-free so you can focus on building a great company. Visit our website or connect with us on LinkedIn to learn more.

Hosted by Matt Gardner, CEO and Co-Founder of Hiline. New episodes drop every other Thursday.

In this episode of the Fiscally Awesome Podcast, host Matt Gardner (Co-founder and CEO of Hiline) sits down with Dave Wieseneck, Expert in Residence at Ramp, for a deep dive into the evolving world of finance and accounting technology.

Dave and Matt explore how modern finance professionals are leveraging automation and AI to move beyond transaction processing and deliver true strategic value. As former auditors who've navigated similar career paths, they share candid insights about:

• The current state of finance technology and how it's finally catching up to other departments
• Why the traditional accounting skillset is being rapidly transformed by AI and automation
• How finance teams can architect the right tech stack for their organization's needs
• The bottlenecks preventing wider adoption of modern finance tools
• What finance professionals should be automating right now
• The exciting future where finance teams deploy AI agents to handle routine tasks

Whether you're a finance professional looking to stay ahead of industry trends, a founder wanting to modernize your financial operations, or simply curious about how AI is reshaping traditional roles, this conversation offers practical wisdom from two industry veterans.

About Fiscally Awesome
Want to unfu*k your finances? Fiscally Awesome is produced by Hiline, where we make small business finances stress-free so you can focus on building a great company. Visit our website or connect with us on LinkedIn to learn more.

Hosted by Matt Gardner, CEO and Co-Founder of Hiline. New episodes drop every other Thursday.

In this episode of Fiscally Awesome, Hiline CEO Matt Gardner sits down with multi-time founder Jeff Knauss to dig into the financial realities of scaling a service business.

Jeff shares the unfiltered truth about his journey from building Digital Hive (ranked 52nd on the Inc. 5000) to his successful exit and newest venture, Arcovo AI. From bootstrapped beginnings with a three-month-old at home to managing rapid growth, Jeff offers practical wisdom on:

1. Why "sales cures all" and how to develop this critical function beyond founder-led selling
2. Building and maintaining a championship team culture that drives performance
3. How to approach financial management when you "don't know what a P&L is"
4. The emerging opportunities in AI automation for small businesses
5. Why the most successful entrepreneurs obsess over how they spend their time

Whether you're running an agency, building a service business, or just trying to make sense of your financial data, this conversation delivers straight talk on what it really takes to build a fiscally awesome company.

Subscribe for more insights that make finance fun again!

Ever wonder what happens when you mix a millennial leader, his boomer dad, and a dash of fortune 500 consulting? Join Matt Gardner as he chats with Robby Riggs, the Oklahoma-born founder who turned The Bridge into a global consulting powerhouse (and just sold it to North Highland – talk about a power move!).

In this episode, Robby dishes on everything from navigating four generations in the workplace to why your accountant's boring spreadsheets might be holding you back. Plus, find out why he wrote a leadership book with his dad after a heated Thanksgiving day argument.

What you'll learn:

1. Why slapping AI on top of your messy data is like putting lipstick on a pig
2. How to stop being the "I'll just do it myself" entrepreneur
3. Why your fancy MBA might actually be making you dumber in 2025
4. How to lead teams when you're not the smartest person in the room (and why that's a good thing)
5. The real reason your finance team is stuck in 1995

Whether you're a small business owner trying to make sense of your numbers, or a leader wondering why Gen Z keeps rolling their eyes at you, Robby's got the straight talk you need. Come for the leadership wisdom, stay for the dad jokes and bridge puns.

In this episode of Fiscally Awesome, Hiline CEO Matt Gardner connects with Anabel Paksoy, a People Operations virtuoso turned venture capitalist who's redefining both how we work and how we invest.

From scaling OpenDoor from 25 to 600 people in just three years to launching her fund, 43, Anabel's journey shows that understanding humans might be the ultimate superpower in tech.

Check out this episode to learn:

1. Why your people problems exist whether you address them or not (and how that debt compounds!)
2. Why Gen Alpha might actually fix everything wrong with work culture
3. The secret to spotting founder potential
4. How AI is becoming more of a foundational toolkit that every business needs, regardless of industry

We're ditching the HR handbook and getting real about what it takes to build companies people actually want to work for. Whether you're drowning in people ops debt or dreaming of becoming an investor, this episode's packed with wisdom that'll make you rethink everything you know about human capital.

Grab your headphones and hit play!

In this episode of Fiscally Awesome, Hiline CEO Matt Gardner sits down with Darrin Jahnel, CEO and Co-Founder of Jahnel Group, who turned a $70,000 credit card debt into a 150-person powerhouse agency.

Darrin's journey reads like a startup rollercoaster – from Wall Street suits to failed educational software to finding his groove in services.

Darrin drops the gold on:

1. How to build a culture so awesome people willingly work 100-hour weeks (for fun!)
2. Why growing agencies need to rethink their accounting and tax strategy and how to do it.
3. The power of RAG (Retrieval Augmented Generation) and why it's about to change everything

We're cutting through the agency jargon and getting real about what it takes to build a company people actually want to work for. Whether you're drowning in startup debt or trying to figure out how to scale without losing your soul, this episode's packed with insights that'll make you rethink everything you know about company culture.

So grab your beer pong ball, settle in, and get ready to learn why sometimes the best business strategy is just caring more than everyone else.

In this episode of Fiscally Awesome, Hiline CEO Matt Gardner sits down with Harini Karthik, a data genius who's gone from wrangling Target's massive datasets to democratizing data analytics for small businesses with her company Zetta.

Harini's journey reads like a who's who of tech powerhouses – GoFundMe, Shipped, Loom. And now she's on a mission to make data accessible to the businesses that need it most.

Harini drops some serious knowledge bombs on:

1. Why waiting 30 days for insights is a no-go for growth
2. How AI is turning months of data work into days and saving small businesses millions
3. Why spreadsheets are like training wheels for your business (it's time to level up!)
4. The future of work where everyone's an entrepreneur with AI sidekicks

Whether you're still tracking customers in Excel or drowning in disconnected data points, this episode's packed with insights that'll make you rethink how you run your business.

So settle in and get ready to learn why data doesn't have to be scary anymore.

In this episode of Fiscally Awesome, Hiline CEO Matt Gardner chats with Joseph Cabrera, a former military leader turned business whisperer who's helping shape the future of small business ownership at Main Shares. (Fun fact: He's the one who gave Matt his first podcast interview!)

Joseph's journey reads like an action movie script – from jumping out of planes in Afghanistan to navigating Silicon Valley boardrooms, with a dash of entrepreneurial wisdom from his mom's small business adventures.

Joseph drops some serious knowledge on:

1. Why 11 trillion (yes, TRILLION) dollars worth of small businesses will change hands this decade
2. How to turn trades experts into business owners (spoiler: you don't need to be rich!)
3. Why treating your financials like a "necessary evil" is killing your business
4. The secret wisdom his mom shared that changed everything

We're cutting through the business jargon and getting real about what it takes to keep America's small businesses thriving. Whether you're a plumber dreaming of owning your own shop, a business owner planning your exit, or just curious about the future of main street America, this episode's packed with insights that'll make you rethink what's possible.

So grab your coffee (or your wrench!), settle in, and get ready to learn why the next generation of business owners might be wearing work boots instead of wingtips.