Jack Siney: How a Business Pivot Turned Rejection Into a Nine-Figure Valuation
The Behavioral Profit Show

Jack Siney: How a Business Pivot Turned Rejection Into a Nine-Figure Valuation

Debbie Longo | Episode : 52 | 15m | August 24, 2026
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In this episode of Behavioral Profit, Debbie Longo speaks with Jack Siney about business pivots, market feedback, change management, and the willingness to change direction when an idea is not producing the expected results.

Jack shares the story of GovSpend, a company he co-founded to help government agencies purchase more efficiently. The original concept aggregated government purchasing data so agencies could compare vendors, pricing, and purchases. After investing significant time, money, and effort into the technology, Jack and his partner took the idea directly to government purchasing professionals—and the response was overwhelmingly negative.

Rather than abandoning the technology, they examined the value of the data and began asking who else could benefit from it. That process led to a complete business-model pivot. Instead of selling the database to government agencies, they offered it to government contractors that wanted insight into what agencies were purchasing, who they were buying from, and what they were paying.

The change required far more than a new sales pitch. Jack explains that they changed their marketing, website, CRM, contacts, processes, and target customer. The new market responded positively, the product took off, and the company operated successfully for more than 12 years before being sold to private equity.

Debbie and Jack discuss the behavioral side of making major business changes. Entrepreneurs can become emotionally attached to an idea because of the time, money, and energy already invested. Moving forward sometimes requires accepting that the original plan is not working, listening to feedback, changing your mindset, and being willing to take a completely different approach.

Jack explains that the market will tell business owners what works if they are willing to listen. At the same time, he cautions against changing direction because of one person's opinion. His approach was to pay close attention when the same feedback appeared three or four times because repeated feedback often signals a real issue that needs to be addressed.

The pivot ultimately helped GovSpend grow to a nine-figure valuation, demonstrating how a business that begins in the wrong direction can achieve significant success when its leaders remain open to change.

This episode explores business pivots, entrepreneurship, market feedback, change management, leadership behavior, adaptability, business growth, decision-making, resilience, and taking action when something is no longer working.

Contact Debbie Longo, Executive Behavioral Coach, Founder and CEO Life In Bloom NY

Behavioral Profit

Website: https://www.debbielongo.com/

Email: debbie@lifeinbloomny.net

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Contact Jack Siney

Jack Siney, Co-Founder + Chief Revenue Officer at FrontRace

Email: jack@frontrace.com

Web: www.frontrace.com

Welcome to the Behavioral Profit Show, where

we look at the behavior behind business results.

I'm your host, Debbie Longo, executive behavioral

coach. And on this show, we go beyond strategy,

talk about the decisions, communication patterns,

leadership behaviors and internal shifts that

shape trust, culture, performance and profit.

Today's conversation is about what really drives

change, not just what people say they want, but

the behaviors they create, the results they get.

We have a very special guest today, Saini. Good

afternoon, Saini. Welcome to the show. Hey, Debbie.

How are you? Nice to meet you. Hi, good. Thank

you for being here. I'm going to ask you today

to give an example of a workplace environment

that you have experienced, whether it's your

company that you own or someplace that you have

worked previously where you had something happen.

an issue, and then you were able to resolve it.

And what was that process? And I'm going to ask

you if you could focus on the process as much

as possible, because a lot of times when listeners

listen, or they wanna try to identify, they're

going to, most of the time, listen to what the

actual situation is, right? And when we look

at the process of something, that kinda helps

us decide whether we wanna get out of that specific

situation or not. So whatever the thing is or

the situation you're gonna be talking about might

not be the exact same thing that the listener

is in the same problem or whatever that they're

in, but they will be able to identify with the

process and then they will be able to insert

their own situation because a lot of these things

we can just do it that way and we could make

the process similar to everything that we do.

And then that's how we're going to solve the

problem. And then the end result to your example

is going to be positive. So you, you solve this

problem. and it worked out great. And that's

gonna give the listener a little bit of a hope

or know that there's a solution. to whatever

issue that they're having in their business and

how they don't have to stay in that. They don't

have to sit in that. And that will eventually

hurt their business. So if you could do that

for me, I would appreciate it. Thank you. Yeah.

So what immediately comes to mind from my end

is my previous company was a company called GovSpend.

GovSpend was we aggregated purchase orders from

government agencies. So imagine city of Orlando,

city of St. Louis, Broward County. We took everything

that they purchased, put it in this big online

database, and the goal was to help government

procure more efficiently. That's where we started,

which is really interesting because the company

we had before that, we helped public safety agencies

be more efficient. Prior to that, we put technology

in police cars to help public safety officers

operate more efficiently. So that was our background.

From that company started GovSpend, which again,

our initial goal was to help government agencies

buy more efficiently. We saw them buy, say, an

AED. One agency would buy an AED for 200 bucks.

The next agency would buy it for $300. You're

like, that doesn't seem good. And there has to

be the exact same device. A week later, you'd

be like, that doesn't seem right. When we started

Gulfspan, we put together all this data to save

for every agency in Florida. Then we went to

the Florida Purchasing Show. So all the purchasing

people get together outside in a big hotel outside

Orlando. Huge show every single year. We're a

vendor. We walk around, start telling people

this idea, and they hated it. And they literally

hated it. I mean, they were just like, let me

get this straight. You're taking our data, jiggering

it, bringing it all together, and then quasi

-selling it back to us? No shot. I mean, they

literally, we were at this show. They almost

threw us out of the show as a vendor. So many

people combined it. I mean, I'm talking about

hundreds. They were like, not a chance. This

is a horrible idea. There's no chance we're giving

you our public data. You're going to aggregate

it all. normalize it and sell it back to us,

dead on the ride. So we had been in this by way

a good year. So we were in it part of it. We're

up to our neck at this point, went home, left

that show, my partner and I sideways. That night

you lay in bed, you stare at the ceiling. You're

like, Oh, this could be bad. This idea that we

had, we thought was so great. Thousands of dollars

invested in it. A lot of effort deal with agencies,

what have you. What happened is we started to

look at the data set we saw. We thought it was

amazing. There were so many insights. When you

have all this data, it's so many insights. And

then we just kept talking through it. We kept

whiteboarding it. What would it be? Who can lever

this? We wanted the agencies to use it, right?

Help share best of and what's the best pricing?

What's the best vendors? What happened? We actually

went 180 and wound up offering the database to

the vendors. So we then repositioned the database

and said, hey, not to the government, but to

vendors. Hey, would you like to see what the

city of Orlando is buying, who they're buying

it from and what they pay? And so that pivot

of our core business model. changed the entire

company. Literally went from kind of, if you

sell the government, it typically takes six to

eight months, kind of a long sales cycle. There's

some red tape, RFPs, what have you. So we went

to now selling to private entities, private government

contractors, which happened much quicker. The

financing, the money involved in the deal was

higher. And so our whole perspective changed

from this process of selling to the government

to selling to government contractors. And so

over the course of about a month, we changed

our marketing, we changed our website, we changed

what we did from a process standpoint, our database,

all of our contacts and our CRM had to change.

And so we wound up selling this product and this

solution to government contractors. And it took

off. And we were just clicking along, trying

to figure out where we should be. The government

contractors loved it. Picture a company like

Dell. If you worked for Dell, you could now go

into our database, see Oh, if I'm going to go

talk to this agency, were they on iOS or are

they on Windows? And when's the last time they

bought computers? And who did they buy from?

And what's the average price they're used to

selling? And so for them, it was amazing. It

was an amazing data set. And so it changed the

whole trajectory of our company, changed how

we worked. And so it worked out great. We were

in that business for both plus years, wound up

selling it to a private equity job, which turned

out great a couple of years ago. And I guess

the moral of that story. when I heard you ask

the question was, normally if you have great

attachment to an idea, there's normally a use

case for it. Sometimes it's not what you initially

think though, right? Sometimes you have an idea,

you sit around and you have an idea like, this

will be so good. And then the market will always

tell you, though, when you go out and tell people

in the market, they'll help redirect you. You

just got to follow the cues and you got to follow

the insights and you'll typically get there.

So that would be my that's the story that first

comes to mind when you ask that question. Yeah,

that's interesting. Thank you for that story.

I really appreciate it. I just want to go back

a little bit. What was the what was the bottom

of that story? What was the thing or things that

you knew that you really couldn't continue in

that company? and that you really needed to change,

and what was your thinking in that, and what

really brought you to that whole change that

you just described in detail? I'd say the bottom

of it is, I kind of passed it really quickly,

but it is really humbling. When you're an entrepreneur

and you work on an idea, not one that's just

an idea, you have a lot of cycles in developing

a piece of technology, gathering data, processing

that data. putting it in a big database, and

a lot of cycles, and a lot of hours, and a lot

of costs involved in that, really challenging.

When you go to sell it, the first people you

talk to, they all tell you, no, 100 % we're not

interested, and 100 % we're not paying for this.

And so big miss, all of your brainstorming, all

of your business development stuff, all the ideas

you had for marketing, website, all went south.

And so we were probably in a change management.

bottom of the valley for a couple of weeks trying

to, again, figure out where do we miss? There's

no interest in this. How could we re figure what

we're doing? The data has a lot of learnings

in it. And so that valley, as you called it,

was probably a two to three week effort of like,

this is not good at all. We have a lot of time

and energy sunk into this solution. It has, again,

some inherent value, but we're clearly selling

it to the wrong people. And just talking to companies,

talking to people in the government, the GovTech

world, really helped us see a different angle

of what we could be, how it could work. And so

that's how we started to slowly come out of that

malaise, is just being open to a new idea, a

new repositioning of the solution, which is much

easier said than done. If you lock into a certain

concept in your head, of what it should be, the

ability to kind of pivot away from that and look

at a new, again, we had to wipe out our whole

CRM, all the contacts and find a whole new set

of contacts. We had all government, all these

government contacts from agencies all across

the country, 90 ,000 agencies. And now we had

to go to vendors. Well, there's three million

vendors. So it was a totally different data set,

totally different process. And so really was

just a lot of long days and long nights, the

willingness to pivot, change what you're doing,

change your mindset. was how that really evolved

over a series of weeks. And then I would just

say the encouragement of when you start talking

about it and then to another client, potential

client base, then being positive, then the feedback

you got. Oh, I'm interested. That can be intriguing.

How would it work? How much does it cost? So

you start to get positive vibes and positive

feedback, and then it starts to feed upon itself.

Yeah, that was very interesting. Thank you. So

that was to me sounded like a pretty detailed

explanation and description of the process, which

is exactly what I'm looking for. So a lot of

times in business, I don't know, I'm not really

sure whether I really need to make a change or

not. And I don't really know if the change, which

direction it's gonna go into. And you kind of

touched on that a little bit, but here's the

thing. Sometimes if I think something or if I

think I need to make a change or something, a

lot of times then that means that I should. And

even if I try it, it doesn't always work out

the way that I want, then that's just the way

that it's meant to be. Because a lot of times

it doesn't work out the way that I think it's

gonna work out. or the prediction that I make

or I think rarely, rarely it does. Right. Rarely

it does the way we think it's going to work out.

Rarely does it go that way. That's true. A lot

of times it doesn't, but the way that it works

out and the way that it comes together and all

the people that are involved in it are really

the way that it's meant to be. And if I can just

accept it as that, because if I want to create

a, if I'm have a business that's $200 ,000 a

year and I want to create a million dollar business,

I might get to 800 ,000. So I might not meet

my goal exactly the way that it should be. And

I kind of feel that that was kind of part of

your story within the description that you gave,

but either way, you're pretty happy with the

outcome. And that's kind of the message that

I really want to send based on what we're talking

about here, your story and the way that we're

describing it. So how do you feel today, right

now, about everything you just talked about and

your business and what the results are? Yeah,

I would add to your comment. I think in the business

world, this doesn't apply to all things that

are loved. But in the business world, again,

the market will tell you, right? You can have

all the thoughts you want on a whiteboard. A

lot of things look good in the office or when

you're brainstorming. But just encourage folks

to throw as many things out as you can. The market

will tell you. It doesn't matter what you think

in the conference room. The market will tell

you. The market will tell you what they like,

what they don't like. And you have to be willing

to hear that and take feedback. and change accordingly.

The other dynamic I would say is we always have

this rule, you had to hear it three times. Like

if you go around and you start talking about

your business, you're going to get advice from

a lot of people to do a lot of different things.

Everyone has an opinion. The reality is we really

wouldn't pivot until we heard something a third

time, right? So if you hear something once, you're

like, oh, that might be interesting. If you hear

it twice, you better take note. If you've heard

it now a third time, it's pretty true. If you've

encountered a pushback, an FAQ, a pricing issue

a third time, a real thing. And then you're going

to have to find a way to address that accordingly.

But a lot of times, not for the world particularly,

folks hear something one time and they change

their whole thing. And you're like, no, you don't

want to be so whiffshall that you're going to

change on every piece of feedback. Because again,

everyone has an opinion. But just to encourage

you, once you've heard it three or four times,

now it's real, right? You're going to have to

do some of it. Going back to your question. Yep.

That works out great for us. We, again, we were

in that business for about 12 years, grew it

to a nine figure valuation. And so it was a blessing,

really a blessing. We were able to get, have

that much success on something that started out

in a totally different vein originally. Very,

very good. And I agree with everything that you're

saying and it really makes sense. And that was

a good way to close. And in closing, I would

like to say that Anybody can do anything with

their business. Anybody can make their business

positive. They don't have to sit if they have

a negative situation or they're unhappy with

something in their business, whether it's sales,

profits, whatever the situation is, the example

is, but that can change. And that's only if I

think as a business owner or an executive that

I will allow that to change and I will create

the willingness that something needs to be different

here. I don't want it. to stay the way that it

is now. And if I take the action, then I can

produce a result. But if I sit... and I do nothing

and I talk or I think and no action is taken

and there's no willingness to do anything about

the situation that I know that I'm in that's

hurting me and my business, then nothing's going

to happen. And it's going to continue to go downhill.

So that was good. So thank you for listening

to the Behavioral Profit Show. If this conversation

gave you a new way to think about leadership,

behavior, communication or business growth, make

sure to follow the show. so you don't miss future

episodes. You can also learn more about my work,

upcoming episodes, and guest opportunities at

DebbieLongo .com. And I also have a website,

Grow Shows. I have two podcasts also. So I'm

gonna put both of those links in there. I'm Debbie

Longo, and remember, when you understand the

behavior behind the outcome, you can create stronger

decisions, better communication, and more profitable

results. And I thank you, Cindy, for being on

the show. I really appreciate it.

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