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Kevin Jackson

Friday May 08, 2026

Category: Newsletter

VOB Roundtable Recap 5-5-26

Aloha everyone,

We kicked off with me (Kevin Jackson — Founder, Offsite CFO Services; Co-Founder & Executive Director, VOB Network) looking out at pouring rain on the Big Island, while Kelvin Ching (Kaneohe, HI; financial advisor specializing in tax-free retirement strategies through Kelvin Ching and Associates / Mod Financial) checked in—and GB De Leon (independent insurance broker with USA Benefits Group + regenerative farmer/rancher in KY) was literally on a tractor trying to get cover crops down before the weather hit. GB stayed in the flow listening in while he worked.

From there, we welcomed a few new faces and got right into what people are building.

Nakisha Jolanda Gregory (U.S. Navy Veteran; Gift Opener LLC + “The Crown Confidence Alchemist™” behind Baldie Brigade; workforce/leadership development + PR/relationship marketing) introduced herself and shared her mission: helping veterans translate their military skills into civilian language, walk confidently through the “open doors” of available resources, and build real pipelines between veterans, employers, and support programs—especially with an eye on Hawai?i and Guam. She also shared she’s currently in Virginia (Hampton Roads) for trainings and plans to be back in Hawai?i on May 12. Kelvin immediately invited her to connect and dropped his calendar link.

Mike Verret (Verret & Associates; pitch/presentation and messaging coach — “Stop Rambling and Start Pitching”) framed a theme that kept showing up all meeting: we all know 100% of what we do, but the audience only cares about a small slice—his work is helping people identify that slice and communicate it with confidence, clarity, and impact.

Marc Cole (Senior Franchise Consultant, The YOU Network; helps clients evaluate 400+ franchise brands) gave a quick overview for anyone exploring franchise ownership—how the process mirrors what veterans already know (follow the process, don’t stop at “4” when the system calls for “5”), and how he can help people evaluate fit and options (with many brands offering veteran discounts). That naturally connected to the “gold and silver” conversation that’s been circulating lately.

In the chat (and in the room with us), Tom Lundell (Honolulu, HI; gold & silver savings consultant with soundMoney / 7k Metals) shared his contact info and links for anyone who wanted to follow up on the precious metals lane, that he made a presentation on last week.

Bill Clement (U.S. Navy; Wise Energy Solutions — energy broker) then brought a very practical cost-reduction lane: he helps commercial businesses shop alternative electricity and natural gas plans in deregulated markets. He emphasized there’s no cost to at least confirm whether you’re paying a good rate—and he posted his contact info plus the deregulated-state list into the chat so it can travel with the recap.

Jennifer “Jen” Oliva (Founder & CEO, Jen Oliva Media; former network news producer — TODAY/NBC/Fox/Fox Business/Bloomberg) shared how she helps experts, authors, and people with strong stories earn media exposure (earned media—not ads), and she dropped her site/email into chat before hopping to a client call.

Deb Plennert (Gold Star widow; founder, Precision with Honor Bookkeeping) stayed active in the flow with connector energy—helping bridge who should meet whom and keeping the conversation grounded in real-world execution.

Nikki Gianni (former federal contracting officer; GovCon strategist — The GovCon Architect / The Small Business Architect) shared a resource for veterans with dogs: the Sierra Delta https://www.sierradelta.com/programs program and a path to up to $3,500 for dog training (not limited to service dogs). She also floated a veterans-and-dogs book concept (Chicken Soup-style stories) and invited anyone with a great story to contribute.

We also had several people in the chat who were part of the room even if they didn’t take mic time:

Frank Yeager (VOB President, and ADA & hazard pattern identification — “protect assets and people”) was active in chat, especially checking in on Ryan’s interview process.
Christopher Hunt (CEO/Founder, Blue Prairie Synergy Solutions) shared his LinkedIn/company link.

Midway through, I shared a VOB update: the member directory and Community News are live. The big idea is simple — instead of a random Google search that can send you down rabbit holes of dead links, disconnected numbers, and unmonitored inboxes, we’re building a vetted, veteran-aligned database of programs, services, and real humans you can actually reach. Also when you post an update in Community News, it gives us something concrete we can amplify across the network.” Kelvin also dropped a direct directory link into the chat to make it easy to find.

Then we hit a very “roundtable” moment: a clear ask and quick routing.

Brian Cate (Assistant VP, SouthStar Capital; small business funding/AR financing including government contract financing) asked the room for a commercial insurance broker who can write general liability policies in Washington state. Deb pointed Brian to GB, and Brian confirmed he reached out to GB by email to start the thread.

Jake “The Flagman” Droge (Certified Reverse Mortgage Professional; reverse mortgage specialist — gave a quick update on being in motion and working through the compliance/transition side of his lending world, and he dropped contact info for anyone who wants to connect around senior homeowner solutions. He’s grouped up with other Vet mortgage professionals all at Loan Depot.

Ryan Ballou (TS/SCI-cleared U.S. Army intelligence and operations leader with 10+ years in high-stakes HUMINT/S2X/S3 environments; also listed as an independent social media contractor) shared a strong update on his nonprofit job opportunity with Monterey Bay Economic Partnership: the process expanded into second-round interviews, and he had what he expected to be a final “casual” discussion with the CEO and directors later that afternoon. He also shared that the organization spans affordable housing, technology, literacy, and internet expansion—and even advanced air mobility (UAS drone logistics / VTOL hybrids / electric aircraft)—and he dropped their link into chat. That sparked a useful side conversation on drones, FAA rules, and the difference between legitimate commercial operators and “anyone with a drone.”

We closed on cybersecurity (with the perfect blend of humor and seriousness).

Todd Mitchell (Owner/Consultant, CyberSecurity4biz; Service-Disabled Veteran-Owned Small Business; author of “The Small Business Owner’s Cybersecurity Guide”) got pulled into a follow-up from Brian about a prior intro to a government contractor dealing with CMMC challenges. The thread ended with a very real takeaway: most cybersecurity risk shows up in simple habits, and Todd’s work is designed to make it clear enough that you either tighten the basics immediately—or decide you want an expert in your corner.

Later in the wrap-up, Mark Spenelli (U.S. Army veteran; CDL-A truck driver building the Nature’s Edge Management concept for a veteran-centered rural property/nonprofit) was on the move to his daughter’s tennis match, and when I welcomed Dorothy Smith (Enrolled Agent; founder of DMS tax prep, and IRS/tax-resolution support) back after the post–tax season stretch, Mark jumped in to say she hasn’t taken much time off—she’s been busy helping him work through a tax issue.

If you want a warm intro to anyone from this week, just let me know who you want to meet and why—happy to bridge it.

See you next Roundtable.

Mahalo,

Kevin Jackson
Co-Founder & Executive Director

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Memorial Day

As we approach Memorial Day, we take a moment to remember and honor the fallen.

I’m thinking of those that have passed on, but also the many people I’ve had the immense privilege of getting to know through VOB Network—veterans and allies whose hearts are full of service and honor. The kind of people who don’t just speak gratitude…they live it, quietly, consistently, and with conviction.

That’s also why VOB Network exists. I’ve watched veterans and allies come together with a shared purpose: to help veteran entrepreneurs move from idea to action. We connect veterans with the resources, and support they’ve earned — and we walk beside them every step of the way.

The Pineapple Creed is the heartbeat of how we show up:
Tough on the outside. Solid at the core. Grown to lead.
Grit in the armor. Gold in the heart.

To those we remember this weekend: thank you. We won’t forget.
And to the people still serving—through business, through community, through showing up for others—thank you for carrying the mission forward.

#MemorialDay #Veterans #Service #VeteranOwned #VOBNetwork

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VOB Roundtable Recap – 5/19/26

Hi everyone,

Thanks for showing up for this week’s VOB Roundtable. I love how these calls keep bouncing between “real life” and “real resources” — and somehow we end up with practical next steps every time.

We started out getting to know Frank DiBartolomeo (retired U.S. Air Force Lt Col; public speaking coach for technical professionals at Speak Lead and Succeed / DiBartolomeo Consulting International). Frank shared he’s based in the Charleston, SC area, spent decades as an engineer + Toastmaster, and now helps technical people advance their careers through better public speaking — including 1:1 coaching, group courses, and conference talks. He also mentioned his book, “Speak Well and Prosper,” which he pulled together from years of presentation-focused blogs.

That opened the door for a quick author-to-author moment with Bill Haase (founder of Money Mindset Media; financial literacy educator, author, and podcast host), who noted he’s building a publishing footprint and offered encouragement around spreading your message. Alex Snyder (Army veteran; financial professional with New York Life in the Greater Boston area) was also in the mix early and gave a quick “yes” as the conversation flowed.

From there we shifted into a really meaningful thread Deb Plennert (Gold Star widow; founder of Precision with Honor Bookkeeping — supporting military families, veterans, first responders, and their family-owned businesses) brought to the group: VA education benefits updates and how we can help transitioning vets not fall through the cracks. Deb shared that her 27-year-old son was approved “yesterday” for Fry-related education benefits (something they didn’t think was possible), and that she’s been following changes closely while connecting dots between groups like Honor Box / Patriot Fund / Company Dogs Inc / Sierra Delta (all referenced in the call).

That led perfectly into Mike Hallopy (Director of the Service Dog Division + student coordinator/instructor at Highland Canine Training / School for Dog Trainers). Mike walked us through Highland Canine’s work across police/military canines, service dogs, and pet behavior/obedience — and then zoomed in on their 24-week Master Dog Trainer Program and the practical, hands-on nature of the training (including service-dog outings and bite-work practicals). Most importantly for this group: Mike confirmed Highland Canine is approved to accept VA education benefits for the program and outlined which chapters they’re currently working with. Lisa Bowers (Founder of Office Allies; executive-level admin support + remote bookkeeping) jumped in right there to reinforce what Chapter 35 is commonly used for, and Deb added detail on recent Chapter 35 changes for surviving spouses and children that may matter for vets and families exploring these paths.

Mike also made it clear he’s open to quick “what’s this all about?” phone calls with anyone considering the program, and he’s happy to be a resource for the veteran community. Deb and I also discussed syncing up with Highland Canine’s owner, Jason Ferguson to talk through partnership possibilities and how we can help get the right people into the right lanes.

Later in the call, Meade Kincke (veteran executive advisor; founder/CEO of Imperfektus and “The Recalibrator” speaker/coach) helped us think through podcast distribution and embedding. Meade suggested a simple solution: using a single YouTube playlist link so the site can display all episodes cleanly instead of embedding one at a time. That led into a bigger point: we’re building the member directory + community news + podcasts/resources area to create a sustainable engine that brings eyeballs (and opportunity) back to the VOB ecosystem.

From there, we welcomed back Nakisha Jolanda Gregory (U.S. Navy veteran; PR/relationship marketing + workforce development trainer; host/executive producer of Confidence On Command LIVE; also building community-driven brands like Baldie Brigade Apparel). Nakisha introduced herself as newly in Hawai?i (moved in December), with a heart for helping veterans build confidence and navigate the overwhelm of transition — “buffet style,” one plate at a time.

We also had a strong “Hawai?i thread” running through the call with Kelvin Ching (financial advisor in Hawai?i; Executive Managing Director at Mod Financial and lead at Kelvin Ching and Associates focusing on tax-free retirement strategies), Pete Tingstrom (retired U.S. Army LTC / Green Beret; co-owner of Aloha Oahu Weddings & Events on Kaneohe Bay), and Kevin M. Desler (U.S. Army veteran; cybersecurity specialist building the Cyber Wingman brand).

On the bookkeeping / tax side, Lisa reconnected with Dorothy Smith (Enrolled Agent; founder of DMS Bookkeeping Inc in Memphis; former Air Force financial management professional specializing in tax resolution and helping people respond to IRS letters). Dorothy is actively leaning toward taxes, Lisa is actively leaning away from taxes — which makes this a pretty natural partnership fit.

We then heard from Anitha L. Srinivasan (principal AI engineer; founder/leader behind UpThriveHQ — career trajectory intelligence for veteran transitions). Anitha shared how UpThriveHQ maps skills into viable “role clusters” and uses an AI + probability component to identify the top 20% skills that can drive 80% of the results needed for a target role. Nakisha immediately raised her hand to connect, especially with her capstone project coming up — and I reinforced that making introductions is part of what I do.

Deb also gave a shout-out to Mike “Buzz” Mallon Jr. (U.S. Marine Corps veteran; founder/managing partner at Storyteller Promotions — branded merchandise + culture-driven recognition and event experiences), noting his veteran-heavy chapter community (“Tropic Thunder”) and the strong environment he’s built.

That opened the door to a very practical benefits + business conversation with Gb De Leon (independent insurance broker with USA Benefits Group; also building a regenerative ranching mission alongside his insurance work). Gb shared how he thinks about helping veterans and families leverage options like ChampVA and individualized plans — and then expanded the lens to small businesses, emphasizing that individualized insurance planning can create real cost savings and more flexibility for both employer and employee.

Before we wrapped, we got a quick slice of “where in the world are you” from Mark Spenelli (U.S. Army veteran; CDL-A driver and founder behind a veteran-centered rural property / tiny-home + RV campground model through Nature’s Edge Management). Mark shared he was out near Kentucky Lake / Tennessee River area at the moment.

JR Allan Rey Bilbes (U.S. Navy veteran; entrepreneur with trucking + real estate interests, including SUM DUM GUY LLC) then offered a time-sensitive heads-up: he’d seen news about funding for veterans pursuing a CDL, and he urged schools to apply for the grant before June 17, noting it’s connected to FMCSA and may help veterans avoid using GI Bill benefits for that training (details to be confirmed).

And finally, Chris Hunt (U.S. Navy veteran; President/CEO of Blue Prairie Synergy Solutions — program/project management, technical integration, risk management, and operational excellence) shared how BPSS supports both government and commercial clients — including “save-the-day” project management, auditing, data analysis and trend reporting, and strengthening security posture (identity access, continuity, disaster recovery, etc.). Chris also asked about the best way to share VOB through the Fort Worth Chamber network (where he’s plugged in), and he offered to help bring in people who can enrich the program.

Reminder: if you haven’t yet, go grab your free directory profile and post anything you want shared here under Community News — events, asks, offers, wins, partnerships, all of it.

See you on the next one,

Mahalo,

Kevin Jackson
Co-Founder & Executive Director

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Bill Haase — 2026 National Business Innovator Prime Award Winner!

Big congratulations to Bill Haase — Founder of Money Mindset Media — on receiving the National Business Innovator Prime Award (2026)!

Bill has been part of the VOB family for some time now, and it’s been awesome to watch him keep pushing the conversation forward around financial education, mindset, and practical tools that help people take control of their money decisions.

The award recognizes Bill’s innovation-driven leadership and the impact of his work through Money Mindset Media, including his book, Our Mindset on Money:
It’s Easy to Control, So Why Don’t We?

Proud of you, Bill — and grateful to have you in our community. Link to the full release in the comments. ???

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VOB Roundtable Recap — May 12, 2026

Hey everyone,

We started with Wayne Murray (Founder/CEO, A-1 VA Ratings West — helps veterans improve/maximize VA disability benefits with free evaluations and coaching) and Kevin Jackson (Founder, Offsite CFO Services + Co-Founder/Executive Director, VOB Network — fractional CFO and systems “engineer” for small businesses) catching up and getting the room settled.

Deb Plennert (Founder, Precision with Honor Bookkeeping — Gold Star widow supporting military families, veterans, first responders, and family-owned businesses) brought a new person into the circle right away: Sophia (introduced as a young patriot looking for work and wanting to serve veterans/military; research context). Deb said she has Sophia’s resume, and Kevin asked Deb to send it over.

Deb then asked the group for referrals to CPAs, tax preparers, or Enrolled Agents (veteran preferred, but anyone in our community is welcome). Kelvin Ching (Executive Managing Director, Mod Financial — Hawaii-based financial advisor focused on tax-free retirement strategies and “financial efficiency” for families and business owners) asked if Hawaii-based talent would work, and Deb clarified she prefers U.S.-based (not offshore), but location is flexible. Kevin also clarified that CPA licenses aren’t limited by state in the way people often assume.

Bill Clement (U.S. Navy Chaplain vet; Wise Energy Solutions — energy broker helping commercial businesses lower electricity and gas costs in deregulated markets) gave a quick overview of how he helps business owners reduce utility spend through rate shopping/negotiation and bill review. He also mentioned a new add-on opportunity he’s stepping into with National Utility Refund (expanding beyond just negotiating rates into helping businesses identify and recover utility billing errors/refunds), and said he’s moving that forward right away.

Ryan Ballou (U.S. Army intelligence/operations leader — TS/SCI background; also listed as an independent social media contractor) shared an update on his work with drones and mentioned he’s reaching out to Sara Raley in San Diego.

That staffing thread turned into a strong “helpful resource” moment when Bill Haase (Founder, Money Mindset Media — author/podcaster focused on financial literacy and money behavior) shared county “workforce development” programs that can subsidize hiring by covering wages for an initial period in some cases. Kelvin chimed in that Hawaii has a workforce development option too.

From there, Deb naturally connected the dots back to Bill Clement’s lane—how lowering a big expense like utilities can be a game-changer, especially for high energy-use businesses. Todd Mitchell (Owner/Consultant, CyberSecurity4biz — Navy veteran helping solopreneurs/micro-businesses with practical cybersecurity compliance; author of “The Small Business Owner’s Cybersecurity Guide”) offered to introduce Bill Clement to a venture capitalist in the “data center in a box” space

We also had Brian Cate (SouthStar Capital — helps businesses fund the upfront money for materials/supplies so they can buy first and get paid later) was introduced by Deb as a resource for bridging that cash gap when timing is tight between expenses and customer payments.

On the veteran housing thread, Mike “Buzz” Mallon Jr. (Founder/Managing Partner, Storyteller Promotions — USMC veteran; branding and promotional products partner for events/tradeshows and culture-driven gifting) was part of the conversation and added helpful perspective. Tyler Rue (USMC veteran; Financial Representative, Western & Southern Life — helps individuals and business owners with protection and financial solutions) asked Buzz to connect him to Pam Brown (introduced as working on a veteran housing 501(c)(3); research context: so he could learn how she runs it. Kevin and Deb also talked about intentionally building a working group around veteran housing projects and who needs to be in the room.

Christopher R. Hunt (U.S. Navy veteran; President/CEO, Blue Prairie Synergy Solutions — program/project management, technical integration, risk management, operational excellence) was part of the conversation and added helpful perspective, including wanting to share VOB through the Fort Worth Chamber where he’s active and looking for people who could strengthen the program.

Nikki Gianni (USAF (Ret.); former Federal Contracting Officer — “The Small Business Architect / GovCon Architect,” helping small businesses win government contracts) steered the group into a really practical thread on funding and access around dog training—specifically pointing to Sierra Delta’s programs and describing a pathway where you complete an initial cohort and then apply for grant support to help cover training costs. She said she’d repost the Sierra Delta link in chat, and she also offered to ask BJ (Sierra Delta) about eligibility details when Deb shared she’s trying to help her daughter get a service dog for Complex PTSD and also wants to train a therapy dog to bring to her local VA.

Brian Davis (CEO/Founder, Stealth Tech Services — SDVOSB IT/cyber/cloud provider with infrastructure + IoT and smart-systems focus) shared what he’s been working on in solar/IoT infrastructure and grant-related momentum, and Kevin flagged that Brian could be a strong fit in the broader veteran housing ecosystem. Brian also shared an AI tool he’s been testing (Marblism) to help with outreach/content workflows, and Nikki echoed that it’s been a real time-saver.

Then I walked everyone through the VOB site and member directory—how profiles work, how to message each other directly, and the deeper “why” behind VOB: making it easier for veterans to reach real, vetted resources instead of dead ends and outdated listings.

As we were wrapping, Mark Spenelli (U.S. Army veteran; founder behind Nature’s Edge Management — building a veteran-centered model combining an ADA-minded tiny-home community with a sustainable RV/campground concept) shared his connection to Must See Racing and pointed people to the series site and schedule.

Asks / Offers / Action Items

Deb Plennert: Seeking referrals to CPAs, tax preparers, or Enrolled Agents (veteran preferred; U.S.-based preferred). Also offered to forward Sophia’s resume for anyone needing a virtual assistant-type role.
Kevin Jackson: Asked Deb to send Sophia’s resume; plans to look into workforce development hiring-subsidy programs.
Todd Mitchell: Offered an intro for Bill Clement into the “data center in a box” investor lane; shared the Google Calendar setting path to show declined events.
Bill Clement: Looking for introductions to commercial business owners who want to reduce electricity/gas costs; shared deregulated-state coverage and contact info in chat.
Tyler Rue + Buzz Mallon: Buzz to connect Tyler to Pam Brown re: veteran housing nonprofit learnings.
Chris Hunt: Wants the best path to share VOB through the Fort Worth Chamber and is looking for people who can enrich the program.
Brian Davis: Shared Marblism link and promo codes in chat for anyone who wants to test it.
Mark Spenelli: Shared Must See Racing links and noted the schedule.

If you want a warm intro to someone from today, hit reply with who you’d like to meet and a one-liner on what you’re hoping to do together.

Mahalo,

Kevin Jackson
Co-Founder & Executive Director
Veteran-Owned Business Network

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Mondays with Morry — Happening Tomorrow (2 Live Options)

Tomorrow we’ve got a great opportunity to plug into calm, clarity, and real-life mindset tools with “Mondays with Morry” from MindTrainer-PRO.

Two chances to join live:

• 1:00 PM ET
• 4:00 PM ET

If you’ve been carrying stress, decision fatigue, or just feel like your focus has been scattered lately—this is a simple way to reset and get grounded with a supportive community.

Here’s the link Jason shared for access:
https://mindtrainer-pro.com/home?am_id=Thenomore9to5club

Let’s show up, support, and keep building strong minds alongside strong businesses.

Aloha

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Kevin Jackson

VOB Roundtable Recap 5-5-26

Discussion

Related News

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VOB Roundtable Recap – 5/19/26

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VOB Roundtable Recap — May 12, 2026

Mondays with Morry — Happening Tomorrow (2 Live Options)

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