<![CDATA[Shift & Thrive Podcast: Investor Series]]>https://www.shiftandthrivepodcast.com/s/investor-serieshttps://substackcdn.com/image/fetch/$s_!Jl46!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbcb9e0d3-4aff-4c96-b12c-2bb9b3b8b19d_1000x1000.pngShift & Thrive Podcast: Investor Serieshttps://www.shiftandthrivepodcast.com/s/investor-seriesSubstackSat, 31 Oct 2026 12:02:43 GMT<![CDATA[From Solo Founder to Investor - Paul Oggelsby - Shift & Thrive - Investor Spotlight - Episode # 101]]>https://www.shiftandthrivepodcast.com/p/from-solo-founder-to-investor-paulhttps://www.shiftandthrivepodcast.com/p/from-solo-founder-to-investor-paulThu, 18 Jun 2026 16:02:58 GMTWhat does it take to build a business so well structured that it could run without you? In this Investor Spotlight episode of Shift & Thrive, host Natalie Nathanson talks with Paul Oggelsby, a former IT managed services CEO and Founder, who exited his business in 2022, and now is an investor, chairman, and advisor. Paul shares how a single Reddit post connected him with thousands of struggling founders, the impact the book Traction had on how he ran his company, and why building toward an eventual exit, whether or not you ever plan to sell, leads to stronger decision-making.

In a special Shift & Thrive exclusive, Paul also announces his newest venture, Maturable.io, born from the same blind spot he faced running his own company and later saw in nearly every founder he advised: the lack of real benchmarking data to know where a business truly stands. He built the platform to close exactly that gap for SaaS leaders.

Takeaways:

~ Most blind spots come from isolation, not incompetence. Surround yourself with peers or advisors who can see what you can’t.

~ Without a real benchmark, you’re guessing. Compare your business against others in your space to know where you actually stand.

~ Build your business with the exit in mind, even if you never plan to sell. It forces stronger systems and leadership.

~ Know which pillars of your business are strong and which are weak, then put your energy into closing the weak ones.

~ Adopt a proven framework, such as Traction or EOS, to simplify your fundamentals and align your leadership team.

~ Lead with data, not opinion, when working with technical leaders. Evidence builds trust faster than instinct alone.

~ Expect resistance to obvious fixes. Changing how a leader operates often takes months of repeated, patient guidance.

Quote of the Show:

“Everyone’s fundamentally got the same issues. No matter the market you’re in, everyone’s fighting the same battle, and it’s so much easier if you surround yourself with people on the same journey.” - Paul Oggelsby

Links:

~ LinkedIn: https://www.linkedin.com/in/oggelsby/details/experience/

~ Website: Maturable.io

Ways to Tune In:

~ Spotify:

~ Apple Podcasts:

~ Amazon Music: https://music.amazon.com/podcasts/fa60b654-1955-4055-93df-fdd40c2a5c8f/shift-thrive-ceo-insights-on-driving-change

~ iHeart Radio: https://www.iheart.com/podcast/269-shift-thrive-ceo-insights-166792501

~ Pandora: https://www.pandora.com/podcast/shift-and-thrive-ceo-insights-on-driving-change/PC:1001086797

~ YouTube: https://www.youtube.com/channel/UClf9QxGUxZw_Sv8_4bZP34Q

This show is sponsored by Magnetude Consulting, bringing you the thinking-Power of a Growth Consultancy and the Getting-It-Done Power of a full-service B2B Marketing Agency.

Learn more at: Magnetude Consulting

]]><![CDATA[Why B2B Deals Stall and How to Fix It - Paul Terry - Shift & Thrive - Episode # 97 ]]>https://www.shiftandthrivepodcast.com/p/why-b2b-deals-stall-and-how-to-fixhttps://www.shiftandthrivepodcast.com/p/why-b2b-deals-stall-and-how-to-fixWed, 20 May 2026 14:03:42 GMTWhat does it actually take to lead a commercial transformation before anyone else believes in it, and what happens when the biggest threat to closing a deal is not your competitor, but your buyer’s fear of being wrong? In this Investor Spotlight episode of Shift & Thrive, host Natalie Nathanson sits down with Paul Terry, global go-to-market leader, advisor, and investor at Tech Operators, who brings over 25 years of experience building and scaling international sales teams. Paul shares the hard-earned lessons from leading one of the earliest social selling rollouts at Forrester Research in 2012, before LinkedIn Sales Navigator was even a household name. He and Natalie dig into the evolution of B2B buyer behavior, the FOMU (fear of messing up) phenomenon that is quietly killing deals, and the practical frameworks Paul uses today when advising early and mid-stage tech founders on ICP, international expansion, and go-to-market clarity. Candid, grounded, and full of real examples, this conversation is one every GTM leader and founder needs to hear.

Takeaways:

  • Pre-wire your frontline managers before rolling out any change initiative. They are the culture carriers closest to your team, and without their buy-in, even the best ideas will land in silence.

  • Overcommunicate through multiple channels and formats until it feels repetitive to you. The audience receiving the message needs far more repetition than the leader driving the change.

  • Recognize that today’s buyers fear making the wrong call far more than they fear inaction. Shift your sales motion at the right moment from urgency-driving to comfort-building, and use social proof, peer dinners, and transparent risk conversations to help buyers feel safe saying yes.

  • Narrow your ICP down to a specific wedge before expanding. Targeting everyone is functionally the same as targeting no one, and trying to go broad too soon is one of the most common and costly go-to-market mistakes founders make.

  • Build product-market fit and repeatability in a core market before expanding internationally. Have a proven motion, a defined ICP, and a scalable operation before paying the tax of internationalization.

  • When entering new markets globally, standardize your operations at the corporate level but hire and trust local expertise for that last-mile cultural execution. One size will lose you business; total localization will prevent scale.

  • The fuse is lit the day you say yes. Whether you are joining a PE-backed company or any scaling business, leaders are brought in to fix something, and the expectation for change starts immediately.

Quote of the Show:

  • “Feel the fear and do it anyway. There are a lot of decisions in our lives that can instill uncertainty and fear, but just because we’re afraid of them, that’s not a good enough reason not to do them.”

Links:

Ways to Tune In:

  • Spotify:

  • Apple Podcasts:

This show is sponsored by Magnetude Consulting, bringing you the thinking-Power of a Growth Consultancy and the Getting-It-Done Power of a full-service B2B Marketing Agency.

Learn more at: Magentude Consulting

]]><![CDATA[Funding National Tech - Derek Willis - Shift & Thrive - Investor Spotlight - Episode # 088]]>https://www.shiftandthrivepodcast.com/p/funding-national-tech-derek-willishttps://www.shiftandthrivepodcast.com/p/funding-national-tech-derek-willisWed, 18 Mar 2026 13:00:00 GMTWhat does it actually take to move a dual-use technology from a proven prototype to a scalable, fundable business? In this Investor Spotlight episode of Shift & Thrive, host Natalie Nathanson sits down with Derek Willis, Founder and Managing Partner of Etowah Capital Partners, who has spent more than three decades navigating the space between early-stage innovation and full-scale commercialization. Derek shares hard-won lessons from directing over $35 million in early-stage investments, why readiness level six is the critical inflection point for any tech startup, how founders can protect their cap tables while crossing the Valley of Death, what it really means to find product-market fit in a white-hot market versus a hyped one, and what he looks for in founders beyond credentials. From Silicon Valley in the early 90s to investing in national security technologies today, Derek brings a rare mix of operator instinct and investor discipline to one of the most complex corners of the startup world.

Takeaways:

  • Build dual-use revenue channels early, or struggle to raise. Smart investors require a credible commercial path before writing a check.

  • Bet on founders with battle scars, not just credentials. Investors like Derek look for leaders who have made payroll under pressure and faced real failure; that resilience cannot be taught, only earned.

  • Go-to-market is a one-strike opportunity. When product-market fit is real and a market is white-hot, the entire organization must be aligned and laser-focused. There is rarely a second chance to launch well.

  • Changing an industry standard takes longer than you think; plan for it. Proving a better technology can take six years, and then proving the market takes another six. Runway and conviction are non-negotiable.

  • Relationships built outside formal business settings move the needle most. The people who can solve your biggest problems are often standing next to you. Never underestimate any conversation.

Quote of the Show:

  • “Truly get to know every person you meet. That person could have the answer to one of the problems that you’re working on.”

Links:

Ways to Tune In:

  • Spotify:

  • Apple Podcasts:

This show is sponsored by Magnetude Consulting, bringing you the thinking-Power of a Growth Consultancy and the Getting-It-Done Power of a full-service B2B Marketing Agency.

Learn more at: Magnetude Consulting

]]><![CDATA[What Investors Really Look For - Elena Gantvarg - Shift & Thrive - Investor Spotlight - # 084]]>https://www.shiftandthrivepodcast.com/p/what-investors-really-look-for-elenahttps://www.shiftandthrivepodcast.com/p/what-investors-really-look-for-elenaWed, 18 Feb 2026 15:03:24 GMTIn this Investor Spotlight episode of Shift & Thrive, Natalie Nathanson sits down with Elena Gantvarg, Principal at Flint Capital, to unpack how early-stage investors evaluate startups in today’s rapidly evolving market. Elena shares firsthand stories of portfolio transformations, explains why product-led growth has become a baseline expectation rather than a differentiator, and offers a candid look at what founders often misunderstand about go-to-market, scaling speed, and U.S. market entry. The conversation explores how culture, leadership decisions, and execution discipline increasingly separate companies that scale from those that stall.

Takeaways:

  • Be willing to evolve leadership as the company scales. The founder or CEO who gets a company off the ground may not be the right person to lead it through hypergrowth, and recognizing that early can unlock the next stage of value creation.

  • Focus on execution over ideas at the seed stage. Investors care far more about the team’s ability to sell, adapt, and execute than the originality of the idea itself.

  • Treat product-led growth as a baseline, not a strategy. Buyers expect to experience value immediately, but PLG alone won’t close deals without strong sales execution behind it.

  • Design your go-to-market for your industry, not trends. What works in enterprise software may fail in digital health or regulated markets, so tailor GTM decisions to how buyers actually purchase.

  • Prove U.S. market traction before scaling aggressively. Even small wins in the U.S. signal cultural and sales readiness and reduce the risk of a costly expansion misstep.

  • Pivot for the right reasons, not impatience. Course corrections should be driven by real market signals and constraints, not by the assumption that another market or idea will be easier.

Quote of the Show:

  • “ What has changed the most during the last few years with Go-To-Market is that the buyers don’t want to be sold to. They want to touch the product and realize the value immediately.”

Links:

Ways to Tune In:

  • Spotify:

  • Apple Podcasts:

This show is sponsored by Magnetude Consulting, bringing you the thinking-Power of a Growth Consultancy and the Getting-It-Done Power of a full-service B2B Marketing Agency.

Learn more at: Magnetude Consulting

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