Extraordinary Pursuits by BIP Ventures

The Startup Hypergrowth Playbook: Lessons from PlayOn! Sports

Hypergrowth is the stuff of dreams and legends for many startups. For those who achieve it, it’s also one of their greatest challenges. Scaling at an accelerated pace can unlock massive opportunities – provided it’s executed with a disciplined strategy. The key to navigating hypergrowth toward opportunity (not chaos) lies in balancing agility and sustainability and making data-driven decisions in the face of overwhelming decisions.
Companies that master hypergrowth don’t just expand rapidly; they evolve strategically. Those that figure out when to push forward aggressively and when to refine processes are best positioned to turn momentum into lasting market dominance.
In this episode of the Extraordinary Pursuits podcast by BIP Ventures, PlayOn! Sports CEO David Rudolph shares his journey leading a company through hypergrowth. He breaks down how PlayOn! transitioned from chasing growth to harnessing it to transform the company from a startup to a sector leader. This episode is an honest look at the challenges, turning points, excitement, and learnings from a startup leader who lived the ‘dream.’
Timestamps:
[02:16] David’s career background and journey into entrepreneurship
[04:43] The problem that inspired David to create PlayOn!
[06:54] The genesis of PlayOn! and where they are now
[11:48] How, where, and when PlayOn! hit hypergrowth
[23:02] Balancing data and action in scaling a company
[29:04] How PlayOn! went from chasing growth to harnessing it strategically
[31:29] David’s advice to startups pursuing high growth
[36:38] Lessons David wishes he knew when he started as an entrepreneur
[39:56] Where to learn more about PlayOn! and its family of brands
Points of Wisdom:
“Have a theory, and be prepared as you can, but ultimately, you’ve to put your product into the market and see how the market responds.” [22:30]
“There’s part of hypergrowth that is luck, and you’ve to be as prepared as possible so when that moment shows up in your company, you can capitalize on it.” [31:54]
“If you try to stick with the plan you imagined at the start, you’re going to miss the opportunity.” [32:33]
About David Rudolph:
David Rudolph is the CEO of PlayOn! Sports, a cutting-edge technology company that has revolutionized how people connect, engage, and experience digital content. Under David’s leadership, PlayOn! has become the central source for high school fun engagement. It encompasses everything from the ticketing process to streaming events. Their innovation has revolutionized how we experience high school sports. David’s entrepreneurial vision and leadership have positioned him as a dynamic force in the industry, driving innovation and growth at an unprecedented scale.
NFHS Network: https://nfhsnetwork.playonsports.com/overview
GoFan: https://gofan.playonsports.com/overview
VidSwap: https://www.playonsports.com/analytics
VNN: https://www.playonsports.com/products/vnn 
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Mini-Episode: The Power of Regional Investor Networks

In this mini-episode of the Extraordinary Pursuits podcast, Venture Atlanta CEO Allyson Eman zeroes in on why networking and preparation are critical elements of a healthy startup ecosystem.
She explains how and why Venture Atlanta has connected early-stage innovation companies with investors since 2007. Pulling from the near 20-year history of the event, she offers useful insights for founders and investors to prepare to succeed at Venture Atlanta specifically and venture capital in general. Listen in for her useful guidance. 
Key Points 
Differentiation and solid connections matter more than having $1M in revenue.  
Do your research so you can be smart about who you reach out to and why.  
Looking at a company online isn’t enough – talk to them, look at their growth, and review their financials. 
Most startups are unlikely to experience hockey stick growth – and investors know better when they see that projected in a pitch deck. 
If you connect with someone, look them up afterward, make sure they are the right person, and follow up with them. 
About Allyson Eman 
Allyson Eman is a seasoned professional with over 30 years of experience in marketing, communications, sales leadership, and business development. Since 2007, she has served as Executive Director, and later CEO, of Venture Atlanta, the largest venture capital conference on the East Coast. Under her leadership, the conference has grown significantly, attracting over 1,500 attendees and helping emerging technology companies raise over $7.5 billion. Before Venture Atlanta, Allyson was key in expanding SouthStar Funding from a small team to a nationally respected mortgage lender and managed marketing for SouthTrust Bank's Georgia branches. She holds a BS from the University of Florida. LinkedIn  
About Venture Atlanta
The Venture Atlanta Conference has evolved from a two-day, high-caliber event into a full-blown community dedicated to bringing innovative companies, disruptive technologies, and top-tier investors together. The 2025 Venture Atlanta event is happening on October 15th and 16th. Sponsorships are open, and startups can apply to pitch starting in May. 
Learn more, sponsor, and prepare to apply
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The Reality of VC Returns: Why Batting Average Beats the Power Law

The Power Law of Venture Capital is the theory that an exceedingly small number – as little as 5-10% of an investor's venture capital investments – will yield the vast majority (90-100%) of returns from venture investing. In a special interview for the Extraordinary Pursuits podcast, BIP Capital CEO Mark Buffington argues that this definition of the Power Law is (at best) extreme.
Buffington explains why venture capital investors and founders should not accept playing a game where 10% of investments generate a 25x, and everything else is basically a write-off. 
This episode will give you an insider's knowledge of why Batting Average is a better measure of a VC's ability to generate the best possible outcomes for everyone they serve.
If you're a founder, listen in to understand what questions to ask when considering a long-term VC partner and how much capital to pursue to balance risk with optimal outcomes. If you're an investor, you'll gain more clarity about the risks inherent in chasing a small number of high returns.
Timestamps
[02:06] The Power Law and how it has shifted over time in Venture Capital
[03:51] Mark's contrarian perspective on Power Law
[06:43] The usefulness of a Batting Average approach to outcomes
[12:33] The role of risk management
[18:56] The impact of extreme Power Law on VC investors 
[22:48] The balance of skill and luck
[26:52] AI's influence on Power Law dynamics
Points of Wisdom
 "Too many times people try to fund their way to category leaders, that's earned with the customers that you have, not the amount of capital that comes." [09:06]
"Founders need to be thoughtful about where they take the money and how much capital they take in based on their level of product fit and market sophistication." [10:04]
"Getting alignment is important; assessing the risk and gaps is super important." [15:39]
About Mark Buffington
Mark Buffington is the co-founder and CEO of BIP Capital and the Managing Partner of BIP Ventures. Since founding BIP Capital in 2006, he has guided the firm to become one of the most recognized venture capital brands outside Silicon Valley, leading investments in over 80 companies across industries such as healthcare, fintech, and enterprise SaaS. Mark serves on several corporate and nonprofit boards, reflecting his commitment to innovation and community impact. LinkedIn
Resources Mentioned
The Power Law of Venture Capital article
The Current and Future State of AI 
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Delivering Value to Distinct Buyer Audiences

Great companies are built on and driven by clear GTM strategies, a specific ICP, consistent messaging, and disciplined metrics. Those steps are fairly straightforward when that company has a single audience to serve. But it’s almost a given that a business will have more than one audience. Most have a set of buyers who then have their own set of constituents. As the source provider, you must understand what constitutes value for each – then meet those distinct needs thoughtfully and consistently, and be aware of how they may be evolving. 
The key to success lies in understanding which of your audiences is the ICP and which are secondary targets and then mapping your offerings to what each one needs and wants most. The process demands focus and flexibility. When a business succeeds in the effort, partnerships thrive, channels widen, and the business is positioned for exponential impact. 
In this episode of the Extraordinary Pursuits podcast from BIP Ventures, HealtheMed CEO Steve Pontius shares strategies and tactics for understanding and addressing multiple audiences' needs. He shares examples of how HealtheMed has grown by organizing its sales and marketing efforts to satisfy the distinct requirements of two very distinct audiences – healthcare providers and their patients.  
This is an episode for any company that is striving to grow their buying audiences and build partner channels. 
Let’s get started. 
Timestamps: 
[00:01] Intro and a bit about our guest, Steve Pontius
[03:07] Steve’s career journey and how he got into entrepreneurship 
[07:21] About HealtheMed and its mission to serve underserved populations
[09:12] The challenge that sparked Steve’s interest (in just 45 seconds)
[11:51] How HealtheMed delivers solutions to its audience 
[14:43] HealtheMed's main buying constituent and solution
[19:04] Key sales and data points for building strong partnerships  
[23:58] How HealtheMed works inside the home
[29:09] How HealtheMed mitigates challenges in remote monitoring 
[31:50] Steve’s advice on how to get to the core of what your audience needs
[35:22] How to reach out and connect with Steve 
Points of Wisdom: 
“If you’re going to be an entrepreneur, one of the best questions you can ever ask is WHY.” [05:39]
“The story is way more important; the data is a supplement.” [17:53]
“Clients have their own concerns, and they are legit; whether we think they should be or not, it doesn’t matter.” [30:46]
“The start-ups that get there get there (do so) because they keep pushing and talking to everybody; this is the only way to be successful.” [34:41] 
About Steve Pontius: 
Steve Pontius is the CEO of HealtheMed, a groundbreaking organization delivering in-home health healthcare and support to underserved populations in Minnesota. He has decades of entrepreneurial, operational and marketing experience within complex businesses in the healthcare space, including Minute Clinic. Under Steve’s leadership, HealtheMed is bridging gaps by bringing innovative technology and care into the homes of the people who need it most. HealtheMed has improved access to vital care services, the health and longevity of typically underserved populations, and the outcomes for caregivers and the healthcare system.   
 
Website: https://healthemed.com/ 
LinkedIn: https://www.linkedin.com/in/stevepontius/ 
 
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Mini-Episode: Driving Startup Growth Through Effective CRM Use

In this episode of the Extraordinary Pursuits podcast, host Rachelle Karamoto speaks with Brendan Tolleson, co-founder and CEO of RevPartners, about the importance of revenue operations (rev ops) and customer relationship management (CRM) systems for startups. They discuss how to effectively harness data, the triggers for implementing a CRM, and the best CRM options for early-stage companies. The conversation emphasizes the need for efficiency and sustainable growth in the current venture capital landscape.
Points of Wisdom: 
"Be generous. Share it."
Timestamps: 
02:47 Understanding CRM's Role in Revenue Operations
05:56 Choosing the Right CRM for Startups
About Brendan Tolleson: 
Tolleson is the founder and CEO of RevPartners, a firm that designs, builds, and executes revenue operations to support its holistic go-to-market strategies for scaling companies. Brendan is a HubSpot expert who leads RevPartners in designing, building, and executing RevOps strategies to support high-growth companies. Before founding RevPartners, he held leadership roles at companies like Cprime, TaxConnex, and Tricentis.  
Website: https://revpartners.io/ LinkedIn: https://www.linkedin.com/in/brendan-tolleson-hubolutionary/ 
🎧 Listen to and watch this episode and other episodes of the Extraordinary Pursuits podcast. 

The Key to Leadership Communication

In many workplaces, “conversations” are actually more like broadcasts—leaders talk and teams listen, but real engagement is missing. In others, the dialogue flows freely, ideas are exchanged, and collaboration thrives. In the first instance, leadership talks AT people, while in the other, people talk WITH each other. Particularly in fast-moving environments, it can feel like effective leadership hinges on delivering messages—dictating strategies, giving orders, and requiring answers. Research shows that successful outcomes and organizational endurance come from the quality of the connections between the people working together. Genuine communication builds critical levels of trust that lay a foundation for necessary candor and ensure every voice is heard.
Shifting from monologue to meaningful conversation is more than a cultural imperative. Healthy team dynamics can shape the health of the organization. In this episode of the Extraordinary Pursuits podcast from BIP Ventures, Chris Kisley joins host Rachelle Kuramoto to share strategies for effective and productive conversations even in resource-constrained and fast-moving companies. Chris is the founder and leader of leadership and organizational development firm Kisley & Wild. She offers decades of experience and perspective on how fast-changing businesses can successfully navigate team dynamics as they evolve—so that they CAN evolve.
Timestamps:
[02:29] Christina’s entrepreneurship journey running Kisley & Wild
[03:48] The motivation behind Christina’s transition from corporate to entrepreneurship
[07:41] Leadership communication: What ‘Talking at one another’ means
[10:54] How leaders can avoid ‘Talking at People’ and enhance communication
[12:37] How to reset a conversation when things start going wrong
[15:31] Practical tips on how to move past ‘Talking at’ to ‘Talking with’
[18:55] Managing team dynamics and relationships in a high-growth environment
[22:26] Case study: The consequences of neglecting people in leadership
[27:30] Red flags to watch out for when managing team dynamics
[30:51] Strategies for building cohesion in hybrid and return-to-office workplaces
[35:57] The one thing you need to become a better communicator in the workplace
Points of Wisdom:
“Communication is meant to be two ways, but sometimes we get too excited about what we’re talking about and don’t pay attention to the fact that there is somebody else.” [07:43]
“If you forget that humans are human beings, not human doing, you can move fast with the work but slow with people.” [10:14]
“What you invest in is where you will get results; if you don’t invest in people, your results won’t come through people, and people do the work of the company.” [19:29]
“Ask for feedback to figure out what it feels like to be on the other side; if you don’t ask, you won’t be told.” [35:51]
About Christina Kisley:
Christina Kisley is the founder of Kisley and Wild, a Leadership and Organizational Development firm dedicated to transforming how leaders communicate and collaborate to create healthy, scalable work environments. With a career spanning three decades, Christina brings deep expertise as a leadership strategist and executive coach. Her extensive experience has given her a unique understanding of the unique challenges leaders face, and she has a proven track record of helping them turn challenges into opportunities for growth and success.
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Mini-Episode: Why Founders Thrive in Atlanta

In this episode of the Extraordinary Pursuits podcast, Alex Gonzalez, Chief Innovation and Marketing Officer for the Metro Atlanta Chamber joins host Rachelle Kuramoto to discuss why Atlanta is a leading startup market. The conversation covers the collaborative nature of Atlanta's startup ecosystem, the importance of talent and diversity, and initiatives aimed at fostering innovation and entrepreneurship in the region. Alex also shares some of the specific ways Atlanta is positioning itself as a top innovation hub – offering a list of action items for listeners. 
Points of Wisdom: 
 "It's all about belonging."
Timestamps: 
01:31 The Collaborative Spirit of Atlanta 
03:54 Building a Talent-Driven Ecosystem in Atlanta 
About Alex Gonzalez: 
Alex Gonzalez is a prolific speaker and writer whose book Disruptor has become a guide for innovators across enterprise, midsize, and startup businesses. He is also the chief innovation and marketing officer for the Metro Atlanta Chamber, a role that gives him a distinct and direct perspective of the Southeastern startup ecosystem. Alex has a hand in launching and expanding significant initiatives directed at building our region's innovation capacity, including ATL Unlocked, the Atlanta Growth Collective, and the Atlanta – Where You Belong initiative. 
🎧 Listen to and watch this episode and other episodes of the Extraordinary Pursuits podcast. 

Beyond the Pitch: Communicating with Confidence

Every founder has a story, but the ones who rise above the noise are those who can articulate their WHY with clarity and conviction. Your WHY is more than just a mission statement—it’s the heartbeat of your vision, the lens through which others see your purpose, and the driving force that inspires trust and investment. It’s what makes you memorable, relatable, and irreplaceable. Beyond the pitch deck, your WHY communicates how you’re wired, what truly matters to you, and why you are uniquely positioned to tackle the challenges ahead.
In this episode of the Extraordinary Pursuits podcast from BIP Ventures, Tara Flickinger from ON Search Partners shares ways for startup leaders to step confidently into the spotlight. Tara explains how to communicate in ways that will leave a positive indelible impression. She offers steps for differentiating yourself, standing out, and inspiring confidence. She also provides recommendations for ways to show up with clarity that motivates others and builds trust with investors.
Timestamps:
[02:15] Tara's background and her role at ON Search Partners
[03:17] How Tara got into the talent and financial industry
[07:23] How to communicate your WHY effectively and why it is important
[09:56] Practical steps to simplify and separate personal and business WHY
[12:08] How to reframe and overcome impostor syndrome
[14:24] Ways to tap into your WHY, differentiate yourself, and be memorable
[20:00] Forgiveness vs. permission: Balancing confidence, assertiveness, and humility
[23:21] Tara’s WHY and passion for the talent space
Points of Wisdom:
“The investors are investing in the person, as much as they are investing in the company, and the better they are able to communicate their WHY, the more they are going to gain the trust of the investors and ultimately the investment.” [08:16]
“Differentiate yourself and be memorable so you are not just another founder.” [14:54]
“If a founder comes across very confident and convicted in their ask and what they are looking for vs. asking for permission, they resonate more with investors.” [21:05]
Resources Mentioned:
Start with why: TED Talk by Simon Sinek: https://www.youtube.com/watch?v=u4ZoJKF_VuA.
About Tara Flickinger:
Tara Flickinger is a partner and executive committee member at ON Search Partners, a retained talent search firm specializing in VP, C-level, and board searches. Tara came to ON Search Partners from Parker Executive Search, and before that, Goldman Sachs. She earned an MBA at the University of North Carolina Keenan-Flagler Business School and a BA from Brown University, where she captained the women's golf team. Tara brings extensive experience with environments that demand presence and presentation.
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Mini-Episode: Building a Strong Foundation for Go-to-Market Success

On this episode of Extraordinary Pursuits, BIP Ventures Chief Performance Officer Christy Johnson is joined by Hailey Devlin and Jason Moore, co-founders of DNA Partners. Hailey brings over a decade of experience in sales, marketing, and product leadership, while Jason is a seasoned entrepreneur with two successful exits. Together, they bring a depth of knowledge and tips for creating operational clarity, improving leadership, and prioritizing communication. Their approach emphasizes the importance of simple, scalable systems that can support long-term growth. 
Timestamps: 
00:55 Building a Content Foundation for Startups 
04:10 The Importance of Iteration and Lean Practices 
Points of Wisdom: 
"Don't aim for perfection; aim for progress." 
About Haley Devlin and Jason Moore 
Haley Devlin is a Growth, GTM, and Operations Consultant with over a decade of expertise in sales, marketing, and product leadership. Jason Moore is a specialist in operations, sales, and executive leadership. He founded and scaled two companies. Together, these industry experts share tips for setting up a successful recruitment approach that builds a winning team, leverages strengths, and establishes a solid foundation for sustainable growth. 
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Essential Annual Planning Strategies for Startup Leaders with Christy Johnson

As we step into a new year, strategic leaders pause to consider what went well and what to do in the year ahead. That process begins with an annual retrospective. For startups—especially those that are in an intense growth mode—an annual retrospective is a crucial exercise. It clarifies what worked, what didn’t, and why from internal and external perspectives and from subjective and objective perspectives. The process requires exercises like team SWOTs and customer surveys. This result is a broad view that can help uncover blind spots and provide the necessary context for setting informed, measurable, effective goals for the coming year.
In this episode of the Extraordinary Pursuits podcast, BIP Ventures Chief Performance Officer Christy Johnson shares insights based on decades of experience as a startup executive and a venture investor. She explains what startup leadership should prioritize at the start of a new year—from conducting an annual retrospective to setting measurable goals and KPIs. Christy also offers actionable advice on aligning teams, creating visibility, and fostering accountability.
Whether you’re revisiting your strategy or planning for growth, this timely episode is packed with invaluable counsel.
Timestamps:
[01:58] Christy's career background and role on the operating side
[04:11] The core components of annual strategic retrospective planning
[10:20] Conducting surveys effectively with minimal cost and time
[13:51] How to maximize value from SWOT analysis and surveys
[18:39] Key considerations for assessing performance and building KPIs
[20:00] Leadership responsibilities: visibility, alignment, and accountability
[26:12] Tracking and adjusting KPIs based on your strategy throughout the year
[30:26] Where to start and what to prioritize now
[33:19] Wrap up and end of the show
Points of Wisdom:
“It’s not just about the metrics and how you do it, it’s about all the rich context around that, both externally and internally, and making sure every person has a voice.” [08:52]
“If you’re trying to do an external analysis of competitors, have your success and sales team contribute because they have a unique lens from talking to customers and prospects all the time.” [14:40]
“When people understand all the different mechanics of what makes a company successful, they tend to make better decisions about how they contribute, and it’s easier to set goals for individuals and teams.” [24:15]
About Christy Johnson:
Christy Johnson is the Chief Performance Officer and General Partner at BIP Ventures. With over 30 years of experience, she has worked with small and scaling companies, gaining hands-on expertise in what it takes to build thriving organizations. From rolling up her sleeves in early-stage startups to leading a technology business as CEO, Christy has experienced the full spectrum of business challenges. Her journey has provided a deep understanding of the obstacles founders and leaders face, making her a valuable resource in helping companies navigate their growth.
At BIP Ventures, Christy partners with portfolio companies to unlock the insights that drive sustainable growth, focusing on efficient scaling, data-driven decisions, and organizational design. Her work includes guiding executive teams to build strong foundations before scaling aggressively and serving as a trusted advisor to help leaders sharpen their decisions and overcome challenges. Follow Christy on LinkedIn.
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